My life, short version to 2020
Just a short bio on how I came to my present state of ambivalence.
I was in the Royal Navy for a time and on one occasion in married quarters a neighbour mentioned that he wanted to see a film. Margaret, my wife, said that she would like to see it as well and asked if I minded if she went with Steve (a Petty Officer on the Royal Yacht, with quite a reputation with the ladies). Now, during the long hours at sea I had started reading men’s magazines, particularly Fiesta which had a section about Readers’ Wives with pics and stories. Men submitted pictures of their partners and wrote letters about how turned on they got from showing off their wives – and even how great a thrill they got from having them fuck other men! I have to admit to getting quite turned on by the thought. So now that an opportunity presented itself, I jumped at it. When the evening came for the “date” I was quite impressed with her appearance – knee length boots, tights, mini skirt and blouse. She really was very pretty at the age of 20. Off she went, and I spent some hours on tenterhooks. They came back rather later than I expected though she had told me they would “probably go for a drink after”. She did look rather flustered though – and no longer wore her tights! On reflection, I should have owned up there and then that I was positive that she had fucked Steve (in his old-style Mini Cooper!) and I most certainly didn’t mind. In the event I kept my thoughts to myself but really relished the love-making that night as I slipped into her well-lubricated body.
Later in my marriage and shortly after I returned from a period at sea, I was informed by a friend that my wife had been having an affair. She had been working as a barmaid and on several occasions she had taken this guy home with her in the early hours of the morning. It didn't need much imagination to work out what was happening. And imagine I did. Instead of being furious I was totally aroused. I couldn't stop imagining my wife getting fucked by this guy. Eventually I confronted her, and she admitted it, begging forgiveness etc. I forced her to give me the full details whilst making love to her. I came in torrents! For a while I was satisfied by listening time after time to the gory, beautiful details until I craved for more. After quite some time I persuaded my wife to have another affair. I think she didn't trust me and thought I was just trying to catch her out to get a divorce but eventually she agreed. That was the start of a long procession of lovers
There was one young lad she would go with one night a week and come home well and truly fucked! Once I waited outside his house and watched. I saw her come out of the bathroom unbuttoning her blouse and walking into his bedroom. Unfortunately, his bedroom curtains were drawn and his parents were still up but the thought of her going in to a 21-year old lad to be fucked was mind-blowing. Better still, when she got home an hour later I got her to undress in front of the fire and squat on my face (see pic right). I knew the wetness I tasted was his and her cums, but this only added to my excitement.
Now I was determined to watch her but she totally refused a threesome, indeed now seemed reluctant to even tell me the details of her affairs. She knew the agreement was that I was to get my thrills from her descriptions of the sex she was getting but it seemed that she was happy to enjoy herself without having to give me my thrills. I tried everything from tapping the phone calls she was getting and making, to recording the conversations and sounds of love-making in her car but what I really needed was to watch. I was still reading Fiesta which had articles and letters by the score describing what was commonly called wife-watching, so I was obviously not alone in fantasising about this. It was from one letter that I got the idea of drilling a small hole in the ceiling of our bedroom. I let her know that I would particularly get turned on by her being fucked in our own bed, though I suspected she was doing this anyway, and arranged to be working away one Wednesday when I knew that her lover had the same afternoon off as she did.
Naturally I didn't go anywhere - except up in the loft. I was quite certain that something was going to happen when my wife came home from work and went straight up to the bedroom, got undressed, had a shower and put on matching bra and pants, and stockings. She slipped on her dressing gown and went downstairs. It was stifling hot and uncomfortable up there and I strained to hear sounds from downstairs. After what seemed like ages I heard the dog bark. By getting my eye as close to the hole as possible I could just about see the stairs. My heart was in my mouth as minutes later I saw her lover walk up those stairs followed by my wife and into the bedroom. As they faced each other my wife slipped off her dressing gown and reached up to put her arms around him and kiss him full on the mouth. She is only 5' 1" and he was over 6ft. They were directly under me, only inches away. She let him go and dropped to her knees. Seconds later I had the incredibly erotic sight of my wife feeding his hard, white cock into her mouth with her small hand wrapped around it. He fucked her mouth for a few minutes before lifting her to her feet and unclasping her bra. He pushed her back onto the bed, OUR bed, and sucked at a nipple whilst feeding her pants over her hips and off onto the floor. She opened her legs wide and I could see her wetness glisten as his spare hand slipped up to her cunt and played. Then, shit, they got into the bed and pulled up the bedclothes.
They fucked three times - but out of sight under the duvet. And she went under the sheets on each occasion to clean him with her mouth. After over an hour of this he dressed and left. My wife left to pick up the kids from school shortly after and I managed to get down and escape.
I managed to watch on a further three occasions, but only once were they completely uncovered. Then at last I saw this tall blonde god thrusting in and out of my little wife's body. My God, it was beautiful. And the sucking! She managed to get his (a disappointingly medium-sized) cock completely into her mouth. She always did a better job on him than she did on me - and she swallowed at least once that I saw.
He left the country shortly after and things changed between my wife and me. She became less willing to recount details of her past affairs whilst we made love and no longer dressed in miniskirt and see-through blouse when we went out - which occasions became fewer and fewer anyway. She seemed to become middle-aged and frumpy almost overnight and seemed to lose all inclinations for any more affairs.
Eventually I met someone who worked for me for a while. She was fantastic. Very good-looking, a brunette to my wife's blonde, intelligent, empathic and very, very imaginative. I owned a couple of shops then, and on more than one occasion she would squat under the counter and suck me to completion whilst a customer was in the shop. She would regularly ask me for a fantasy. Once I said I wanted her to come to work naked. The next morning, she walked through the door in her beige trench coat and stood there with her back to the street. She slowly undid the belt and buttons and opened it up to show me her naked, gorgeous body.
Another time when asked for a fantasy I remarked that I had always wanted a blow job whilst driving my car in daylight. That happened about a week later the way to a trade show in Bournemouth. On the way, she pulled up her skirt flashing her stocking tops (she always wore stockings) to lorry drivers. Then, minutes before we came off the dual carriageway she leant over, unzipped me and took me in her mouth. I came in a few short great minutes. Licking me clean she sat up and fingered some stray come back in her mouth saying how lovely it tasted. She loved to suck and always, always swallowed. In fact, in the three months I knew her she sucked me off dozens and dozens of times, but we only fucked on three occasions. She preferred to suck than fuck. I suppose it was about then that I seriously started wondering what it would be like, after all she seem to get so much out of it. I think that, like her, I preferred to please people rather than getting pleasure myself, so this would be a part of that process.
On one occasion after much begging I finally got her to divulge one of her fantasies. She wanted to make love in the open with people watching. With little hesitation I took the opportunity to drive to the New Forest. We found a semi-secluded spot and lay out a blanket and started to kiss and cuddle. Within a few minutes we had an audience. One was a gentleman in Barbour jacket and tweed flat cap, the other a young forestry worker. As soon as she was aware that her audience had arrived, she set to work, flashing, sucking, fucking. It ended up doggy fashion followed by her licking me clean. It was fantastic, playing to the gallery.
Unfortunately, my wife discovered our affair and as my girlfriend’s husband was in the police, she made it so difficult for him that he was transferred. After that no more women were allowed to work with me. I started to take on young lads for work experience and I well remember one, in particular, called Jeff. The moment he walked through the door, for the first time in my life, I thought "he's beautiful" and I actually fancied a male. Nothing overt ever came of it but I often fantasised about him but in real life I arranged a cunning plot. I had a good selection of real porn magazines which I kept hidden at the shop (my wife won't let me keep them) and I let him "discover" the hiding place. Then one day I told him I had to go out for half an hour after closing but was expecting an important call so could he sit in the back room after locking me out until I came back.
I had hidden a security CCTV connected to a recorder in the back room. When I got back and let him go my hands were shaking as I played it back. The temptation was, as I suspected, too much and he had got out my books. Not two feet from the camera he wanked himself over the pictures. I could plainly see when he shot his come out all over the floor. I had hoped that he would have come into some tissues I had cunningly left there so I could have had a close-up afterwards but no, he even scrubbed the come with his shoes to hide the evidence. It was the most erotic blue movie I had ever seen. I did it three more times and got a kick each time. I had included a gay mag in the pile hoping that he would at least show a passing interest, but he quickly discarded it. I took him for a drink a few times but never had the courage to make a pass. Shortly after he got married and left the area.
Andrea seemed to enjoy giving a blowjob so much (she preferred it to fucking) I got to wondering what it would be like. My real turn on is seeing others get turned on! Does that make sense? Ideally, I would like a threesome with Margaret and another guy. I went on YuVuTu and put myself down as bi-curious, plus kept a close eye on the M2M forums. I did post on there a couple of times and replied to some other invitations. I think there are a lot of bi-curious men out there as I had more than a few contacts but most fizzled out, mainly them not having the bottle to meet up.
Then I saw a re-post from someone I had been in contact with, but nothing came of it. I mailed him and two days later I was in his house with his wife out for a couple of hours. It was his first time as well so there was a bit of hesitation on both sides, but we took the plunge, stripped and shyly looked at each other. He is about 27, good looking and tanned. I suggested I start, and he sat on sofa with me between his knees - and I proceeded to give him the best BJ he had ever received (his words). He came quickly and in my mouth which I swallowed. I really didn’t think I had got the amount I had fantasised about. He later mailed to say he had a wank before I got there! He didn't want me to cum in his mouth - fine by me, I got what I went for and I was now no longer a BJ virgin!
A couple of weeks later I got a call from him – he needed another BJ as he had enjoyed the last so much, though he thought it may be his last as he and his wife wanted a baby and he didn’t want to jeopardise his relationship. The second meeting was a good as the first with the benefit that we could relax this time. We photo’d and videoed our tryst and this time he came loads! The taste wasn’t unpleasant – in fact it didn’t taste of much at all; certainly, the amount was copious but not anywhere near as thick as I had assumed it would be. I know he really enjoyed it again, but he said that as he and his wife were now trying for a baby and he had “scratched his itch” he would not be asking for anymore meets. I certainly respected his wishes; as always, my partner is in charge. I get my kicks vicariously not by forcing my wishes on my partners
An opportunity arose for me when Margaret went away for a week. The guy from Southampton who I had chickened out on previously, as he seemed to want to go too far, too fast, contacted me again but as this time was possibly my only and last opportunity for complete privacy I agreed to a meet at my place. I decided that I would experience just about everything left for me to do just to see if it turned me on!
He had done the lot on a previous occasion with another guy and persuaded me to try it. I, being an organiser, went to town. I got on the web and ordered butt plug and lubricant, I shaved, before he came I showered and cleaned myself out inside and out (and put in the butt plug, weird feeling but it stays in due to its shape and stretches your arse for things to come!), I then put out drinks and snacks to keep us going.
He arrived; a nice guy, well-spoken, quite slim and well dressed. I had provided dressing gowns, so we got undressed and talked for a bit over glasses of wine (his choice) telling our stories. He has had quite an interesting life but his wife is quite ill, long term, so he hasn’t had sex with her for years.
We then went upstairs; I had put a bath towel on bed and rigged up cameras (with his permission). I had also set up a projector playing selected porn on the bedroom wall. Slipping off the robes we did some serious sucking for a while until he suggested that he fuck my arse. He had a condom (as had I), took out my butt plug and lubricated me with my little black bottle (£5.95 – dearer than champagne!). He then proceeded to fuck my arse. His cock was long but thin (thank god) and he really hammered the length into me, banging me somewhere deep up my arse. What did I think? – well, it was certainly different. I think that except for the fact he was so long I would have enjoyed it more but the banging deep inside was a bit off-putting, even slightly painful. He did come, but in the condom of course so I didn’t actually feel anything (shame, I was hoping for that experience, but I realise the dangers).
After another drink, he asked me to fuck him. Out came the lube again and he lay down arse up in the air. I slipped on my condom and proceeded to fuck him. He certainly enjoyed it (especially when I played with his cock while fucking his rather tight arse - no butt plug there!). Did I enjoy it? Well, yes, I suppose so, not so much physically as it was much the same as any other fuck but as it was the first time I had fucked a man’s arse that added a bit of something. I didn’t come though, I’m not sure why. We did spend quite some time sucking after that and the score was 2-2 by the time he had to go home.
All in all, an afternoon to remember. For quite some time after I seriously thought that I would call it a day as I had done just about everything I had fantasised about, so I haven’t made contact or even looked on that site since. I had though joined another site, xHamster, which aroused my interest once more with its wide range of subjects and some good videos.
I was regularly surfing xHamster and I began to notice the number of “friends” I was gathering who wore panties in their profile pictures. One guy, in particular, lived just down the road from me and after many private messages between us we eventually got me meet up at his lovely big house. I was not totally surprised to find him wearing a G-string under his dressing gown and we got on very well indeed as we talked of our experiences and expectations. It was his first time with a man and really his nervousness didn’t lead to the most satisfactory of meetings. But he did enjoy it and wanted a re-match. He asked me about my “feminine side” and whether I dressed up much. Actually, I hadn’t (except in my youth – go on, we’ve all done that!) but it did arouse my curiosity and one day when the wife was out, I tried on a few of her things – and certainly got aroused. I also looked at the massive range of cross-dressing videos on Yuvutu and xHamster and my arousal got even stronger!
I joined FabGuys and what a revelation. Basically, it’s all about casual sex with all sorts as members. You define what you are after (I entered a wide-ranging specification!!!) and it shows you those available in the local area on an hour-by-hour basis, even sending to your smartphone. You load up your preferences, a few pics (which can be kept private or made public) and wait for the contacts. I had only been on a while and had many assignations. My profile was really a reflection of all I have put on here but it was the cross dressing that really got the responses. It appears that even “straight” men can’t resist playing with a CD. As luck would have it, Margaret went back up North with our (male) friend for four days and I had fun every day. I wonder whether she did. He was certainly up for it.
I get as many opportunities as I want nowadays through this site, from a MMM where I was the junior partner and ordered to suck and fuck; to being the dominant to a submissive; to getting a call to rush out and give a BJ almost literally in passing. And of course, as is my wont, I always swallow. It really turns me on seeing others in *******. And I really do give a wonderful blow job even if I say so myself.
What I really wanted was to fulfil my greatest wish of an MFM - a woman with no inhibitions, feeding my cock into the other guy’s mouth, encouraging him to play with me and me with him. And even, whisper it, spit roast and DP. Heaven. And then it happened. A guy on Fabswingers was arranging an MFM but after I had expressed interest he disappeared. The next thing I know I was organising a meet at the Ibis Hotel in Portsmouth. This is a budget hotel which most importantly has rooms free from 12:00. There was a lot of messing about trying to get people to confirm; lots asked to be there, but their profiles were inadequate. I needed them to be bi and show their pictures. Many on the site don’t though, often just have a picture of their cock. So I had a list including standbys. The girl had said that she wanted her very first gang bang and I didn’t want to let her down. She also wanted some guys in lingerie, something I was only too glad to go along with. So, on the day I booked in and shortly after there were six men all over Annette. Every combination you could think of and she responded fantastically with moans, screams and violent shaking. I got to fulfil a long-standing wish, underneath her while she sucked my cock and I was inches away from a cock pounding into a steaming, soaking reddened cunt. I fucked her arse while another was in her cunt and a cock in her mouth. I even, slut that I now am, licked up cum that had been sprayed over her tits and passed it into her mouth to the cheers of the crowd. After they had all gone she thanked me in her own way and I came gallons all over her.
The next thing I knew I was contacted by someone who I had given a blow job to the year before. He was back with his missus after a break when he had gone off with another, more adventurous, women. His wife was now back and had agreed to spice up their love life and was willing to have a MFM – as he knew me I was invited. My first MFM then and I saw the wife watching in awe as her hubby gave me a blow job, then she joined me giving him one. She squirted all over my face as I went 69s with her with her husband above me
Fabguys definitely the way to go for fun but an awful lot of time-wasters and fantasists without the balls to do anything about it. For example, I managed a late-night fuck for someone who had been let down and was desperate. A long drive but made up for by a tall, slim, beautifully dressed guy with tight arse and who adored me spraying his face.
One time. as alfresco fun was out of the question due to the weather, I decided to try the Tropics in Portsmouth, a gay sauna and my first time. Not that I’m a shy person but it was no problem – we are all there for the same thing anyway. Lots of dark rooms, steam rooms, saunas, videos going continually, private rooms if wanted and lube and condoms provided. Parking was in Sainsbury’s immediately next door and the entrance was out of the way and discreet.
No-one was “dressed” (except for the towel provided) that day but apparently there are several days a month where it is encouraged. I had prepared myself to be fucked but ran out of time (parking limited to 2 hours at Sainsbury’s but a big car park opposite and I spent most of that finding my way round). Quite busy though and I got and gave BJs including a big black cock – my first. Costs £15 but worth it for the privacy, safety and facilities.
I got the message from FabGuys that second Wednesday of the month was dress-up day at Tropics. Various comments on the site indicated that it was indeed anything goes so I determined to go for it. I showered early in the morning before anyone else was up and shaved all over really close. Later I had the house to myself, so I fully prepared myself, cleaning and thoroughly lubricating my arse. I checked with my life-size dildo that I was clean and slack enough before putting on stockings, sussie and the cutest pair of flowered panties I “found” in Margaret’s drawer. All I needed to do now when I got there was to wrap around my mini kilt and bolero top, slip on my wig and a fetching white knitted hat and I was ready to go. But I didn’t.
I got an invite from Fabguys from a guy from Hamble half my age who had a free house for a couple of hours. Well, I thought, why not save £15, I could always go to Tropics another time (and I will).
So I turned up at this guy’s house and he was waiting all prepared, wearing wifey’s panties and holdups. Straight into the bedroom where he pushed me back to lie there open and inviting – and he accepted the invite. He kissed and caressed me all over and I just lay there, eyes firmly closed (not that he was bad looking, but in my mind, he was a young Felicity Kendall, Jennifer Aniston and Gwyneth Paltrow, all rolled into one). Soon he was licking and sucking my cock and it would have been rude not to reciprocate. Seven inches of warm rigid flesh soon filled my mouth and I worked on it with relish much to his satisfaction. After all the preliminary fun he got down to the real action. I had pulled into a lay-by before arriving and slipped a thoroughly lubricate dildo up my arse to loosen the sphincter and prepare myself for this, no pain on entry for me!
He lifted my nylon clad legs over his shoulders and I wrapped my thighs around his head. His throbbing (yes, it was!) prick probed my arse and with only the slightest hesitation slipped in – deep. He exhaled and paused, then slowly at first withdrew almost the whole length, just a bit quicker this time. Then, withdraw again, and thrust, harder and quicker this time. Then even quicker and harder, he fucked me gentle reader. How was it? Divine!
This was only my third time and it was what I had always dreamed of. I was so wet, he had a cock of the perfect size, and his thrusting was just so right. I wish it had gone on for ever, but this thrusting actually did last a pleasing length of time. Then he started wanking me as well. I have seen many videos of men getting fucked and I was a bit surprised that many did not seem to have much of an erection – mine was really throbbing! Obviously, it appeared my prostate was getting lots of exercise.
His wanking was superb; his breathing was heavy and fast; my body was lifting against his thrusts and I was in total *******. Then we came; yes, we, simultaneously, the holy grail of fucking. His seed spurted deep into my arse on his last thrust and my cum shot up over my pushed-aside panties, over my little kilt and even onto my erect nipples. Best cum I’ve had in ages. And as for his...it was still dripping from my arse the following morning! Previously I had not been over-enthusiastic about being fucked, more curious, but I now know what an experience it can be, I shall definitely do it again (with the right size cock).
Then another first; a genuine, committed transvestite, Julie by name, young and gorgeous. Some great photos of her on Fabguys and you really, really, couldn’t say she wasn’t all female. I was introduced to her profile by a guy who had a motor cruiser on the Hamble. He came from the Midlands, had taken early retirement and spent his time between there and on his boat. I had accepted his invitation for an afternoon of fun. Actually, he wasn’t very virile at all but a great host. Over a glass of wine, he showed me the profile of a regular visitor to his boat, the above Julie. I was awe-struck as to how feminine and great looking she was and when he said that she was going aboard the following evening I begged him to invite me too. He contacted Julie and happily she agreed to a three-some.
We arrived at the same time the following evening. She travelled fully dressed and entirely convincing; other boat-owners watched as we boarded the cruiser and I’m positive they thought she was all women. I don’t, as a rule, kiss men (bar the one exception above) but Julie was so pretty I could not hold back, and I’m very pleased to say she fully reciprocated and for most of the evening we snogged, frenched and canoodled like school-age items. Jeremy had wanted me dressed and Julie certainly had no objections. In no time I was down to my hold-ups, school-girl kilt and top.
Julie just slipped off her panties fully maintaining her feminine personae. Jeremy had a bit of a problem with erections but that night I made up for him. In no time my throbbing cock was in her mouth while Jeremy did what he could to hers. Julie made it very obvious what she wanted; to be fucked, and I was more than happy to do it. For the next hour and a half, yes, that’s right – I had an erection for a fully ninety minutes to Julie’s delight - I fucked her arse in every position; from the front with legs over my shoulders, doggy-style, cow-girl, sideways and so on. I did not want to ever come, as I knew that the evening would probably end there, and I wanted it to never end.
I was amazed at my own staying power and there was a permanent smile on my face, well when it wasn’t being smothered by lipstick-covered plump lips. But the fucking and sucking had, of course, to come to an end. My excuse for being out for the evening expired at nine o’clock so it was with regret that I got her to lie on her stomach with legs clamped tightly together to squeeze my cock in the warm, wet haven then I thrust deeply and quickly to finally cum, and cum… and cum!
I reluctantly dressed, and we said our farewells. You may ask what Jeremy was doing all this time; well, when not directing us he was taking pictures (with our permission of course). These pictures are locked away in a private file on my computer for my enjoyment and to convince myself I was not dreaming.
I was impressed by the effort Julie had put into her looks; the first time on the boat she travelled there fully dressed and walked from the car park past other boat-owners confident that she could pass muster as a woman. She certainly did for me, I couldn’t keep my hands of her. This got me realising that my attempts at cross-dressing were pathetic; the randy schoolgirl’s micro tartan skirt, halter top and a pair of hold-ups. Rather amateurish and definitely not sexy, just another old man being kinky. I determined to put more effort into it, but opportunities hardly ever arose - until one week fairly recently.
My troublesome ******** guest who spoils most of my opportunities was away for the week and my wife went to Chichester with her friend. I have a tracker on her phone (not perfect, often a long delay in updating locations) so I knew that I had the opportunity to put some real effort into my appearance. I went through Margaret’s (very extensive) wardrobe and found the perfect dress, one she doesn’t wear anymore as it’s far too short and she no longer has the legs she had. I padded a bra with some sculpted sponge and glued them into the cups, felt perfect! I then experimented with a touch of makeup. Fully dressed I felt wonderful, no doubt how Julie and other far more convincing CDs than I feel, and worthy of the effort. Having felt so good it was obvious it would be a shame to waste that on just looking in the mirror, so back onto Fabguys and that day I was fondled and fucked by two great cocks, 9” each one. I finished each in my mouth and the cum was copious to my great satisfaction. I had a third on the go waiting when I checked the tracker – she was at Emsworth! I only just got properly dressed (and no, I didn’t forget the makeup thank God) when she walked through the door. Still a day to savour though, despite the close call. I have promised Steve, the last guy, first shot next time.
Then I had temporary access to empty offices in Lee on Solent and took the opportunity to really go to town, well fucked over a desk on several occasions, spit roast and even had a bukkake! I also got round to buying my own clothes and make-up and included a pair of thigh-high “fuck-me” boots. What a slut I’ve become.
One of the highlights of having the office to myself for hours at a time was the ability to really play – visitors every half-hour was perfect, and once with three guys I got my first bukkake! What an experience.
So, what was the future going to be for me? I was so impressed with Julie’s dressing efforts, and some others on Fabguys, together with my attempt, I’d like a girlie session one day. The problem is my perception of T-girls. I only wanted to see Julie as a woman, “him” coming into a hotel room in jeans and T shirt before getting changed into “her” really would spoil the image and the anticipation for me.
The second meet on the boat he came in plain clothes and changed into “her” in the small shower room. I deliberately averted my eyes the whole time. I didn’t feel I could kiss a man; I certainly could kiss a “Julie” (and did, incessantly). Now if I could get around that problem, a meet would be high on the agenda. Tropics may be a solution, very dark in there lol.
Just before Christmas I had another hotel room booked and managed to entertain seven guys, getting fucked five times and getting seven mouthfuls. Only one threesome unfortunately and a lovely spit roast. Timing is always difficult especially with the number of fantasists and deliberate time waster there are on Fabguys. I do like that sort of arrangement (the hotel room) though; it gives me the chance to go to town with make-up and clothes.
In January I was invited by a Fabguy regular to join him at a meet in Eastleigh. Married guy with a thing about dressing up and getting fucked – just like me then lol. I was asked not to dress as he wanted to be the centre of attraction. So off I went and was soon knocking at the door with Mike, the other guy, and was let in by a 6’2” slim guy, beautifully and sexily dressed in fishnets and miniskirt. Mike and I quickly undressed and were soon fucking, sucking and getting sucked Angie – and did so for a full hour and a half (and joined by another guy halfway through) before finally finishing in her arse. The other guy actually filled a condom which Mike fed to a greedy Angie. I was most impressed with the morning, particularly my stamina, and I really did envy her the attention she got.
Before the lockdown I was introduced to another bit of fun I hadn’t previously thought of. I met a Tranny called Sharon as part of a threesome at a guy’s flat. He was a waste of space, but Sharon really looked the part, had massive 38DD boobs (not real alas) but was quite slim and attractive (in the dim light that these meets usually take place in lol).
We did have a good time and the following week I was invited to a private session at her flat. I was invited to dress up which I did but was then asked to beat Sharon. I had never given the SM scene any thought before but as I always prefer to please my partner I agreed. I used a leather belt and a multi-stranded whip she had made on her bare arse and back – and I mean hard!
We had a safety word but no matter how hard I whipped her, and she screamed, she would not say it. It was only exhaustion that stopped me, but I was then rewarded with a fantastic fuck followed by me giving her a mouthful where I came loads.
We arranged another session and this time videoed it with three cameras and put it in toto on xHamster and 1-minute snippets on Fabguys on my profiles, both received rave reviews. That session involved a fair bit of violence, ripping off panties, belts and whips, much fucking and culminating in me wanking into an open and very willing mouth. I’d saved my cum for a week for which she was most grateful!
It was an amazing session and, Covid permitting, I’d thought that hopefully it would lead to another, possibly with another top who would fuck us both after helping me whip Sharon senseless. Unfortunately, Sharon had a son who frequented Fabguys and apparently recognised her despite the mask and her tattoos being covered. I never saw her again but heard that there had been signs of great violence at her flat. So it’s okay to watch such fun but no-one is allowed to take part – hypocrisy writ large.
I now was enjoying the thrills I get from dressing en femme, the feel of nylon on my thighs, the cooling breeze stirring my skirt, even my false but firm breasts trusting out of my top. I have greater confidence in my looks, having a reasonably slim figure and have often walked in public dressed, often at the filling station and Lee on Solent seafront
I’d taken to going on a Thursday morning to a local dogging spot, the car park opposite the Royal Armouries at Fort Nelson on Portsdown Hill, Portsmouth. This was the day that the wife went shopping and I could more or less guarantee two or three hours to prepare and have some fun. So, it’s lots of make-up and getting well-dressed to wander round with only some dog-walkers and loads of perves for company. We all know why we’re there, yet so many are nervous and extremely hesitant. Fortunately, there are many who, like me, are either confident or just don’t care. Yes, I’ve been fucked often and almost always get several mouthfuls of cum. I’ve met a couple of other cross-dressers there as well. One, Lesley, is a long-term tranny, doesn’t look, or even try to look, in the least bit feminine but another, Sarah, is convincing. She is a fully committed T-Girl and has lived as a woman since her teens and in my eyes is gorgeous – so much so that I have fucked her a couple of times and, boy, was it fun. Even more fun was when she fucked me! A wonderful surprise and one of, if not the, best fucks I have had. See what you get when you have the confidence to play! I’m really turning into a slut!
My wife regrettably has died of cancer (and I do blame the NHS, my GP in particular, due to their response to Covid) so cuckolding is no longer an option for me.
MMF is the next best thing I suppose but not many Fs willing and available to play it seems. Just a few memories of licking a clit and cock at the same time, then eating the cum out of a soaking cunt. Bliss!
On the plus side I have the house to myself so more opportunities to play.
I also had the opportunity to go, dressed, to a local T-gurls meet at Alwyn’s in his man-cave in the garden. Fully fitted out as a pub with the welcome addition of a pull-out double bed for group entertainment, and private bedrooms for more intimate fun. I’ve met some fantastic gurls there and we’ve all, at one time or another, been fucked by our super-stud host and invited tops. Great meets with the full-range of less-than-convincing to genuine trans gurls. Two in particular, Claire and Nina are actually beautiful!
In July last year I had the great pleasure of a weekend of fun in Liverpool. Four days up North for the Open staying at a Holiday Inn at Albert Docks with easy access and an opportunity for fun that I was unlikely to miss, especially as the weather gave me the excuse to entertain in my room rather than on the course. And entertain I did. Thirteen meets over the four days and what fun I had.
A few other fantasies fulfilled recently as well. I’ve always fancied walking dressed as a “lady of the night” around a lorry park – and I’ve now done that. I’m pleased to say I was invited into a cab in a Fratton lorry park where my miniskirt was removed, I was whipped (I always carry my little flogger in my handbag) and well fucked before having my mouth filled with copious Yorkshire cum! It was so much fun I did it in Southampton too.
On another occasion, on a Saturday night, I was invited to meet someone off Fabguys outside the London Hotel in Southampton. It was really busy and I walked through the partying crowds in my short trench coat and wearing my sexiest stuff – only to find he wasn’t staying there at all, but in the hostel behind for ex-offenders! There were police raiding it at the time. I declined the invite but being jostled in the Saturday party crowd was a massive turn-on.
I’m also fortunate to have experienced many instances of my favourite scenarios – three-and-more-somes! I’ve done this with MMMG, MFM and M,G,G. Guys and gurls, these are great fun and there are many combinations you can get up to.
Is there anything I don’t do? Well, I’ve never seen the fascination for watersports or ***********. Far too messy and requiring a lot of cleaning up afterwards. I did dally with it once with the wife at her request, I think she had a fantasy about, but I think it just ticked a box for her though doing it for her did turn me on.
At my request, most of my meets involve me getting whipped. Why? Well, I’ve found that many, if not most, men secretly get a massive turn-on whipping a peachy arse. On many occasions the whipping session has brough about a premature end to the afternoon as the highly aroused perpetrator of pain found it necessary to quickly finish (often very copiously) in my mouth.
An awful lot of guys fantasise about fucking schoolgirls – and I’m always pleased to oblige. A video I made of this with a very willing volunteer is very popular for some reason lol.
I’m always happy to make videos and role play though not that many guys are willing to show themselves (almost all are married I assume, maybe their wives should keep them happy, or maybe almost every man actually is secretly bisexual!)
Guys, there’s nothing wrong with fantasising. And it’s alright to act out your fantasy – with a willing (and legal) partner.
So, if you’ve read this far then this is me and where I am today. I hope this story encourages you to seize the day, Carpe Diem, like I have. I would so hate to be on my deathbed thinking “I wish I’d…”
Come join me, it’s lovely xxx
Contact me on [email protected] or via xHamster as popeye014
Mike (aka Michaela and Popeye)
I was in the Royal Navy for a time and on one occasion in married quarters a neighbour mentioned that he wanted to see a film. Margaret, my wife, said that she would like to see it as well and asked if I minded if she went with Steve (a Petty Officer on the Royal Yacht, with quite a reputation with the ladies). Now, during the long hours at sea I had started reading men’s magazines, particularly Fiesta which had a section about Readers’ Wives with pics and stories. Men submitted pictures of their partners and wrote letters about how turned on they got from showing off their wives – and even how great a thrill they got from having them fuck other men! I have to admit to getting quite turned on by the thought. So now that an opportunity presented itself, I jumped at it. When the evening came for the “date” I was quite impressed with her appearance – knee length boots, tights, mini skirt and blouse. She really was very pretty at the age of 20. Off she went, and I spent some hours on tenterhooks. They came back rather later than I expected though she had told me they would “probably go for a drink after”. She did look rather flustered though – and no longer wore her tights! On reflection, I should have owned up there and then that I was positive that she had fucked Steve (in his old-style Mini Cooper!) and I most certainly didn’t mind. In the event I kept my thoughts to myself but really relished the love-making that night as I slipped into her well-lubricated body.
Later in my marriage and shortly after I returned from a period at sea, I was informed by a friend that my wife had been having an affair. She had been working as a barmaid and on several occasions she had taken this guy home with her in the early hours of the morning. It didn't need much imagination to work out what was happening. And imagine I did. Instead of being furious I was totally aroused. I couldn't stop imagining my wife getting fucked by this guy. Eventually I confronted her, and she admitted it, begging forgiveness etc. I forced her to give me the full details whilst making love to her. I came in torrents! For a while I was satisfied by listening time after time to the gory, beautiful details until I craved for more. After quite some time I persuaded my wife to have another affair. I think she didn't trust me and thought I was just trying to catch her out to get a divorce but eventually she agreed. That was the start of a long procession of lovers
There was one young lad she would go with one night a week and come home well and truly fucked! Once I waited outside his house and watched. I saw her come out of the bathroom unbuttoning her blouse and walking into his bedroom. Unfortunately, his bedroom curtains were drawn and his parents were still up but the thought of her going in to a 21-year old lad to be fucked was mind-blowing. Better still, when she got home an hour later I got her to undress in front of the fire and squat on my face (see pic right). I knew the wetness I tasted was his and her cums, but this only added to my excitement.
Now I was determined to watch her but she totally refused a threesome, indeed now seemed reluctant to even tell me the details of her affairs. She knew the agreement was that I was to get my thrills from her descriptions of the sex she was getting but it seemed that she was happy to enjoy herself without having to give me my thrills. I tried everything from tapping the phone calls she was getting and making, to recording the conversations and sounds of love-making in her car but what I really needed was to watch. I was still reading Fiesta which had articles and letters by the score describing what was commonly called wife-watching, so I was obviously not alone in fantasising about this. It was from one letter that I got the idea of drilling a small hole in the ceiling of our bedroom. I let her know that I would particularly get turned on by her being fucked in our own bed, though I suspected she was doing this anyway, and arranged to be working away one Wednesday when I knew that her lover had the same afternoon off as she did.
Naturally I didn't go anywhere - except up in the loft. I was quite certain that something was going to happen when my wife came home from work and went straight up to the bedroom, got undressed, had a shower and put on matching bra and pants, and stockings. She slipped on her dressing gown and went downstairs. It was stifling hot and uncomfortable up there and I strained to hear sounds from downstairs. After what seemed like ages I heard the dog bark. By getting my eye as close to the hole as possible I could just about see the stairs. My heart was in my mouth as minutes later I saw her lover walk up those stairs followed by my wife and into the bedroom. As they faced each other my wife slipped off her dressing gown and reached up to put her arms around him and kiss him full on the mouth. She is only 5' 1" and he was over 6ft. They were directly under me, only inches away. She let him go and dropped to her knees. Seconds later I had the incredibly erotic sight of my wife feeding his hard, white cock into her mouth with her small hand wrapped around it. He fucked her mouth for a few minutes before lifting her to her feet and unclasping her bra. He pushed her back onto the bed, OUR bed, and sucked at a nipple whilst feeding her pants over her hips and off onto the floor. She opened her legs wide and I could see her wetness glisten as his spare hand slipped up to her cunt and played. Then, shit, they got into the bed and pulled up the bedclothes.
They fucked three times - but out of sight under the duvet. And she went under the sheets on each occasion to clean him with her mouth. After over an hour of this he dressed and left. My wife left to pick up the kids from school shortly after and I managed to get down and escape.
I managed to watch on a further three occasions, but only once were they completely uncovered. Then at last I saw this tall blonde god thrusting in and out of my little wife's body. My God, it was beautiful. And the sucking! She managed to get his (a disappointingly medium-sized) cock completely into her mouth. She always did a better job on him than she did on me - and she swallowed at least once that I saw.
He left the country shortly after and things changed between my wife and me. She became less willing to recount details of her past affairs whilst we made love and no longer dressed in miniskirt and see-through blouse when we went out - which occasions became fewer and fewer anyway. She seemed to become middle-aged and frumpy almost overnight and seemed to lose all inclinations for any more affairs.
Eventually I met someone who worked for me for a while. She was fantastic. Very good-looking, a brunette to my wife's blonde, intelligent, empathic and very, very imaginative. I owned a couple of shops then, and on more than one occasion she would squat under the counter and suck me to completion whilst a customer was in the shop. She would regularly ask me for a fantasy. Once I said I wanted her to come to work naked. The next morning, she walked through the door in her beige trench coat and stood there with her back to the street. She slowly undid the belt and buttons and opened it up to show me her naked, gorgeous body.
Another time when asked for a fantasy I remarked that I had always wanted a blow job whilst driving my car in daylight. That happened about a week later the way to a trade show in Bournemouth. On the way, she pulled up her skirt flashing her stocking tops (she always wore stockings) to lorry drivers. Then, minutes before we came off the dual carriageway she leant over, unzipped me and took me in her mouth. I came in a few short great minutes. Licking me clean she sat up and fingered some stray come back in her mouth saying how lovely it tasted. She loved to suck and always, always swallowed. In fact, in the three months I knew her she sucked me off dozens and dozens of times, but we only fucked on three occasions. She preferred to suck than fuck. I suppose it was about then that I seriously started wondering what it would be like, after all she seem to get so much out of it. I think that, like her, I preferred to please people rather than getting pleasure myself, so this would be a part of that process.
On one occasion after much begging I finally got her to divulge one of her fantasies. She wanted to make love in the open with people watching. With little hesitation I took the opportunity to drive to the New Forest. We found a semi-secluded spot and lay out a blanket and started to kiss and cuddle. Within a few minutes we had an audience. One was a gentleman in Barbour jacket and tweed flat cap, the other a young forestry worker. As soon as she was aware that her audience had arrived, she set to work, flashing, sucking, fucking. It ended up doggy fashion followed by her licking me clean. It was fantastic, playing to the gallery.
Unfortunately, my wife discovered our affair and as my girlfriend’s husband was in the police, she made it so difficult for him that he was transferred. After that no more women were allowed to work with me. I started to take on young lads for work experience and I well remember one, in particular, called Jeff. The moment he walked through the door, for the first time in my life, I thought "he's beautiful" and I actually fancied a male. Nothing overt ever came of it but I often fantasised about him but in real life I arranged a cunning plot. I had a good selection of real porn magazines which I kept hidden at the shop (my wife won't let me keep them) and I let him "discover" the hiding place. Then one day I told him I had to go out for half an hour after closing but was expecting an important call so could he sit in the back room after locking me out until I came back.
I had hidden a security CCTV connected to a recorder in the back room. When I got back and let him go my hands were shaking as I played it back. The temptation was, as I suspected, too much and he had got out my books. Not two feet from the camera he wanked himself over the pictures. I could plainly see when he shot his come out all over the floor. I had hoped that he would have come into some tissues I had cunningly left there so I could have had a close-up afterwards but no, he even scrubbed the come with his shoes to hide the evidence. It was the most erotic blue movie I had ever seen. I did it three more times and got a kick each time. I had included a gay mag in the pile hoping that he would at least show a passing interest, but he quickly discarded it. I took him for a drink a few times but never had the courage to make a pass. Shortly after he got married and left the area.
Andrea seemed to enjoy giving a blowjob so much (she preferred it to fucking) I got to wondering what it would be like. My real turn on is seeing others get turned on! Does that make sense? Ideally, I would like a threesome with Margaret and another guy. I went on YuVuTu and put myself down as bi-curious, plus kept a close eye on the M2M forums. I did post on there a couple of times and replied to some other invitations. I think there are a lot of bi-curious men out there as I had more than a few contacts but most fizzled out, mainly them not having the bottle to meet up.
Then I saw a re-post from someone I had been in contact with, but nothing came of it. I mailed him and two days later I was in his house with his wife out for a couple of hours. It was his first time as well so there was a bit of hesitation on both sides, but we took the plunge, stripped and shyly looked at each other. He is about 27, good looking and tanned. I suggested I start, and he sat on sofa with me between his knees - and I proceeded to give him the best BJ he had ever received (his words). He came quickly and in my mouth which I swallowed. I really didn’t think I had got the amount I had fantasised about. He later mailed to say he had a wank before I got there! He didn't want me to cum in his mouth - fine by me, I got what I went for and I was now no longer a BJ virgin!
A couple of weeks later I got a call from him – he needed another BJ as he had enjoyed the last so much, though he thought it may be his last as he and his wife wanted a baby and he didn’t want to jeopardise his relationship. The second meeting was a good as the first with the benefit that we could relax this time. We photo’d and videoed our tryst and this time he came loads! The taste wasn’t unpleasant – in fact it didn’t taste of much at all; certainly, the amount was copious but not anywhere near as thick as I had assumed it would be. I know he really enjoyed it again, but he said that as he and his wife were now trying for a baby and he had “scratched his itch” he would not be asking for anymore meets. I certainly respected his wishes; as always, my partner is in charge. I get my kicks vicariously not by forcing my wishes on my partners
An opportunity arose for me when Margaret went away for a week. The guy from Southampton who I had chickened out on previously, as he seemed to want to go too far, too fast, contacted me again but as this time was possibly my only and last opportunity for complete privacy I agreed to a meet at my place. I decided that I would experience just about everything left for me to do just to see if it turned me on!
He had done the lot on a previous occasion with another guy and persuaded me to try it. I, being an organiser, went to town. I got on the web and ordered butt plug and lubricant, I shaved, before he came I showered and cleaned myself out inside and out (and put in the butt plug, weird feeling but it stays in due to its shape and stretches your arse for things to come!), I then put out drinks and snacks to keep us going.
He arrived; a nice guy, well-spoken, quite slim and well dressed. I had provided dressing gowns, so we got undressed and talked for a bit over glasses of wine (his choice) telling our stories. He has had quite an interesting life but his wife is quite ill, long term, so he hasn’t had sex with her for years.
We then went upstairs; I had put a bath towel on bed and rigged up cameras (with his permission). I had also set up a projector playing selected porn on the bedroom wall. Slipping off the robes we did some serious sucking for a while until he suggested that he fuck my arse. He had a condom (as had I), took out my butt plug and lubricated me with my little black bottle (£5.95 – dearer than champagne!). He then proceeded to fuck my arse. His cock was long but thin (thank god) and he really hammered the length into me, banging me somewhere deep up my arse. What did I think? – well, it was certainly different. I think that except for the fact he was so long I would have enjoyed it more but the banging deep inside was a bit off-putting, even slightly painful. He did come, but in the condom of course so I didn’t actually feel anything (shame, I was hoping for that experience, but I realise the dangers).
After another drink, he asked me to fuck him. Out came the lube again and he lay down arse up in the air. I slipped on my condom and proceeded to fuck him. He certainly enjoyed it (especially when I played with his cock while fucking his rather tight arse - no butt plug there!). Did I enjoy it? Well, yes, I suppose so, not so much physically as it was much the same as any other fuck but as it was the first time I had fucked a man’s arse that added a bit of something. I didn’t come though, I’m not sure why. We did spend quite some time sucking after that and the score was 2-2 by the time he had to go home.
All in all, an afternoon to remember. For quite some time after I seriously thought that I would call it a day as I had done just about everything I had fantasised about, so I haven’t made contact or even looked on that site since. I had though joined another site, xHamster, which aroused my interest once more with its wide range of subjects and some good videos.
I was regularly surfing xHamster and I began to notice the number of “friends” I was gathering who wore panties in their profile pictures. One guy, in particular, lived just down the road from me and after many private messages between us we eventually got me meet up at his lovely big house. I was not totally surprised to find him wearing a G-string under his dressing gown and we got on very well indeed as we talked of our experiences and expectations. It was his first time with a man and really his nervousness didn’t lead to the most satisfactory of meetings. But he did enjoy it and wanted a re-match. He asked me about my “feminine side” and whether I dressed up much. Actually, I hadn’t (except in my youth – go on, we’ve all done that!) but it did arouse my curiosity and one day when the wife was out, I tried on a few of her things – and certainly got aroused. I also looked at the massive range of cross-dressing videos on Yuvutu and xHamster and my arousal got even stronger!
I joined FabGuys and what a revelation. Basically, it’s all about casual sex with all sorts as members. You define what you are after (I entered a wide-ranging specification!!!) and it shows you those available in the local area on an hour-by-hour basis, even sending to your smartphone. You load up your preferences, a few pics (which can be kept private or made public) and wait for the contacts. I had only been on a while and had many assignations. My profile was really a reflection of all I have put on here but it was the cross dressing that really got the responses. It appears that even “straight” men can’t resist playing with a CD. As luck would have it, Margaret went back up North with our (male) friend for four days and I had fun every day. I wonder whether she did. He was certainly up for it.
I get as many opportunities as I want nowadays through this site, from a MMM where I was the junior partner and ordered to suck and fuck; to being the dominant to a submissive; to getting a call to rush out and give a BJ almost literally in passing. And of course, as is my wont, I always swallow. It really turns me on seeing others in *******. And I really do give a wonderful blow job even if I say so myself.
What I really wanted was to fulfil my greatest wish of an MFM - a woman with no inhibitions, feeding my cock into the other guy’s mouth, encouraging him to play with me and me with him. And even, whisper it, spit roast and DP. Heaven. And then it happened. A guy on Fabswingers was arranging an MFM but after I had expressed interest he disappeared. The next thing I know I was organising a meet at the Ibis Hotel in Portsmouth. This is a budget hotel which most importantly has rooms free from 12:00. There was a lot of messing about trying to get people to confirm; lots asked to be there, but their profiles were inadequate. I needed them to be bi and show their pictures. Many on the site don’t though, often just have a picture of their cock. So I had a list including standbys. The girl had said that she wanted her very first gang bang and I didn’t want to let her down. She also wanted some guys in lingerie, something I was only too glad to go along with. So, on the day I booked in and shortly after there were six men all over Annette. Every combination you could think of and she responded fantastically with moans, screams and violent shaking. I got to fulfil a long-standing wish, underneath her while she sucked my cock and I was inches away from a cock pounding into a steaming, soaking reddened cunt. I fucked her arse while another was in her cunt and a cock in her mouth. I even, slut that I now am, licked up cum that had been sprayed over her tits and passed it into her mouth to the cheers of the crowd. After they had all gone she thanked me in her own way and I came gallons all over her.
The next thing I knew I was contacted by someone who I had given a blow job to the year before. He was back with his missus after a break when he had gone off with another, more adventurous, women. His wife was now back and had agreed to spice up their love life and was willing to have a MFM – as he knew me I was invited. My first MFM then and I saw the wife watching in awe as her hubby gave me a blow job, then she joined me giving him one. She squirted all over my face as I went 69s with her with her husband above me
Fabguys definitely the way to go for fun but an awful lot of time-wasters and fantasists without the balls to do anything about it. For example, I managed a late-night fuck for someone who had been let down and was desperate. A long drive but made up for by a tall, slim, beautifully dressed guy with tight arse and who adored me spraying his face.
One time. as alfresco fun was out of the question due to the weather, I decided to try the Tropics in Portsmouth, a gay sauna and my first time. Not that I’m a shy person but it was no problem – we are all there for the same thing anyway. Lots of dark rooms, steam rooms, saunas, videos going continually, private rooms if wanted and lube and condoms provided. Parking was in Sainsbury’s immediately next door and the entrance was out of the way and discreet.
No-one was “dressed” (except for the towel provided) that day but apparently there are several days a month where it is encouraged. I had prepared myself to be fucked but ran out of time (parking limited to 2 hours at Sainsbury’s but a big car park opposite and I spent most of that finding my way round). Quite busy though and I got and gave BJs including a big black cock – my first. Costs £15 but worth it for the privacy, safety and facilities.
I got the message from FabGuys that second Wednesday of the month was dress-up day at Tropics. Various comments on the site indicated that it was indeed anything goes so I determined to go for it. I showered early in the morning before anyone else was up and shaved all over really close. Later I had the house to myself, so I fully prepared myself, cleaning and thoroughly lubricating my arse. I checked with my life-size dildo that I was clean and slack enough before putting on stockings, sussie and the cutest pair of flowered panties I “found” in Margaret’s drawer. All I needed to do now when I got there was to wrap around my mini kilt and bolero top, slip on my wig and a fetching white knitted hat and I was ready to go. But I didn’t.
I got an invite from Fabguys from a guy from Hamble half my age who had a free house for a couple of hours. Well, I thought, why not save £15, I could always go to Tropics another time (and I will).
So I turned up at this guy’s house and he was waiting all prepared, wearing wifey’s panties and holdups. Straight into the bedroom where he pushed me back to lie there open and inviting – and he accepted the invite. He kissed and caressed me all over and I just lay there, eyes firmly closed (not that he was bad looking, but in my mind, he was a young Felicity Kendall, Jennifer Aniston and Gwyneth Paltrow, all rolled into one). Soon he was licking and sucking my cock and it would have been rude not to reciprocate. Seven inches of warm rigid flesh soon filled my mouth and I worked on it with relish much to his satisfaction. After all the preliminary fun he got down to the real action. I had pulled into a lay-by before arriving and slipped a thoroughly lubricate dildo up my arse to loosen the sphincter and prepare myself for this, no pain on entry for me!
He lifted my nylon clad legs over his shoulders and I wrapped my thighs around his head. His throbbing (yes, it was!) prick probed my arse and with only the slightest hesitation slipped in – deep. He exhaled and paused, then slowly at first withdrew almost the whole length, just a bit quicker this time. Then, withdraw again, and thrust, harder and quicker this time. Then even quicker and harder, he fucked me gentle reader. How was it? Divine!
This was only my third time and it was what I had always dreamed of. I was so wet, he had a cock of the perfect size, and his thrusting was just so right. I wish it had gone on for ever, but this thrusting actually did last a pleasing length of time. Then he started wanking me as well. I have seen many videos of men getting fucked and I was a bit surprised that many did not seem to have much of an erection – mine was really throbbing! Obviously, it appeared my prostate was getting lots of exercise.
His wanking was superb; his breathing was heavy and fast; my body was lifting against his thrusts and I was in total *******. Then we came; yes, we, simultaneously, the holy grail of fucking. His seed spurted deep into my arse on his last thrust and my cum shot up over my pushed-aside panties, over my little kilt and even onto my erect nipples. Best cum I’ve had in ages. And as for his...it was still dripping from my arse the following morning! Previously I had not been over-enthusiastic about being fucked, more curious, but I now know what an experience it can be, I shall definitely do it again (with the right size cock).
Then another first; a genuine, committed transvestite, Julie by name, young and gorgeous. Some great photos of her on Fabguys and you really, really, couldn’t say she wasn’t all female. I was introduced to her profile by a guy who had a motor cruiser on the Hamble. He came from the Midlands, had taken early retirement and spent his time between there and on his boat. I had accepted his invitation for an afternoon of fun. Actually, he wasn’t very virile at all but a great host. Over a glass of wine, he showed me the profile of a regular visitor to his boat, the above Julie. I was awe-struck as to how feminine and great looking she was and when he said that she was going aboard the following evening I begged him to invite me too. He contacted Julie and happily she agreed to a three-some.
We arrived at the same time the following evening. She travelled fully dressed and entirely convincing; other boat-owners watched as we boarded the cruiser and I’m positive they thought she was all women. I don’t, as a rule, kiss men (bar the one exception above) but Julie was so pretty I could not hold back, and I’m very pleased to say she fully reciprocated and for most of the evening we snogged, frenched and canoodled like school-age items. Jeremy had wanted me dressed and Julie certainly had no objections. In no time I was down to my hold-ups, school-girl kilt and top.
Julie just slipped off her panties fully maintaining her feminine personae. Jeremy had a bit of a problem with erections but that night I made up for him. In no time my throbbing cock was in her mouth while Jeremy did what he could to hers. Julie made it very obvious what she wanted; to be fucked, and I was more than happy to do it. For the next hour and a half, yes, that’s right – I had an erection for a fully ninety minutes to Julie’s delight - I fucked her arse in every position; from the front with legs over my shoulders, doggy-style, cow-girl, sideways and so on. I did not want to ever come, as I knew that the evening would probably end there, and I wanted it to never end.
I was amazed at my own staying power and there was a permanent smile on my face, well when it wasn’t being smothered by lipstick-covered plump lips. But the fucking and sucking had, of course, to come to an end. My excuse for being out for the evening expired at nine o’clock so it was with regret that I got her to lie on her stomach with legs clamped tightly together to squeeze my cock in the warm, wet haven then I thrust deeply and quickly to finally cum, and cum… and cum!
I reluctantly dressed, and we said our farewells. You may ask what Jeremy was doing all this time; well, when not directing us he was taking pictures (with our permission of course). These pictures are locked away in a private file on my computer for my enjoyment and to convince myself I was not dreaming.
I was impressed by the effort Julie had put into her looks; the first time on the boat she travelled there fully dressed and walked from the car park past other boat-owners confident that she could pass muster as a woman. She certainly did for me, I couldn’t keep my hands of her. This got me realising that my attempts at cross-dressing were pathetic; the randy schoolgirl’s micro tartan skirt, halter top and a pair of hold-ups. Rather amateurish and definitely not sexy, just another old man being kinky. I determined to put more effort into it, but opportunities hardly ever arose - until one week fairly recently.
My troublesome ******** guest who spoils most of my opportunities was away for the week and my wife went to Chichester with her friend. I have a tracker on her phone (not perfect, often a long delay in updating locations) so I knew that I had the opportunity to put some real effort into my appearance. I went through Margaret’s (very extensive) wardrobe and found the perfect dress, one she doesn’t wear anymore as it’s far too short and she no longer has the legs she had. I padded a bra with some sculpted sponge and glued them into the cups, felt perfect! I then experimented with a touch of makeup. Fully dressed I felt wonderful, no doubt how Julie and other far more convincing CDs than I feel, and worthy of the effort. Having felt so good it was obvious it would be a shame to waste that on just looking in the mirror, so back onto Fabguys and that day I was fondled and fucked by two great cocks, 9” each one. I finished each in my mouth and the cum was copious to my great satisfaction. I had a third on the go waiting when I checked the tracker – she was at Emsworth! I only just got properly dressed (and no, I didn’t forget the makeup thank God) when she walked through the door. Still a day to savour though, despite the close call. I have promised Steve, the last guy, first shot next time.
Then I had temporary access to empty offices in Lee on Solent and took the opportunity to really go to town, well fucked over a desk on several occasions, spit roast and even had a bukkake! I also got round to buying my own clothes and make-up and included a pair of thigh-high “fuck-me” boots. What a slut I’ve become.
One of the highlights of having the office to myself for hours at a time was the ability to really play – visitors every half-hour was perfect, and once with three guys I got my first bukkake! What an experience.
So, what was the future going to be for me? I was so impressed with Julie’s dressing efforts, and some others on Fabguys, together with my attempt, I’d like a girlie session one day. The problem is my perception of T-girls. I only wanted to see Julie as a woman, “him” coming into a hotel room in jeans and T shirt before getting changed into “her” really would spoil the image and the anticipation for me.
The second meet on the boat he came in plain clothes and changed into “her” in the small shower room. I deliberately averted my eyes the whole time. I didn’t feel I could kiss a man; I certainly could kiss a “Julie” (and did, incessantly). Now if I could get around that problem, a meet would be high on the agenda. Tropics may be a solution, very dark in there lol.
Just before Christmas I had another hotel room booked and managed to entertain seven guys, getting fucked five times and getting seven mouthfuls. Only one threesome unfortunately and a lovely spit roast. Timing is always difficult especially with the number of fantasists and deliberate time waster there are on Fabguys. I do like that sort of arrangement (the hotel room) though; it gives me the chance to go to town with make-up and clothes.
In January I was invited by a Fabguy regular to join him at a meet in Eastleigh. Married guy with a thing about dressing up and getting fucked – just like me then lol. I was asked not to dress as he wanted to be the centre of attraction. So off I went and was soon knocking at the door with Mike, the other guy, and was let in by a 6’2” slim guy, beautifully and sexily dressed in fishnets and miniskirt. Mike and I quickly undressed and were soon fucking, sucking and getting sucked Angie – and did so for a full hour and a half (and joined by another guy halfway through) before finally finishing in her arse. The other guy actually filled a condom which Mike fed to a greedy Angie. I was most impressed with the morning, particularly my stamina, and I really did envy her the attention she got.
Before the lockdown I was introduced to another bit of fun I hadn’t previously thought of. I met a Tranny called Sharon as part of a threesome at a guy’s flat. He was a waste of space, but Sharon really looked the part, had massive 38DD boobs (not real alas) but was quite slim and attractive (in the dim light that these meets usually take place in lol).
We did have a good time and the following week I was invited to a private session at her flat. I was invited to dress up which I did but was then asked to beat Sharon. I had never given the SM scene any thought before but as I always prefer to please my partner I agreed. I used a leather belt and a multi-stranded whip she had made on her bare arse and back – and I mean hard!
We had a safety word but no matter how hard I whipped her, and she screamed, she would not say it. It was only exhaustion that stopped me, but I was then rewarded with a fantastic fuck followed by me giving her a mouthful where I came loads.
We arranged another session and this time videoed it with three cameras and put it in toto on xHamster and 1-minute snippets on Fabguys on my profiles, both received rave reviews. That session involved a fair bit of violence, ripping off panties, belts and whips, much fucking and culminating in me wanking into an open and very willing mouth. I’d saved my cum for a week for which she was most grateful!
It was an amazing session and, Covid permitting, I’d thought that hopefully it would lead to another, possibly with another top who would fuck us both after helping me whip Sharon senseless. Unfortunately, Sharon had a son who frequented Fabguys and apparently recognised her despite the mask and her tattoos being covered. I never saw her again but heard that there had been signs of great violence at her flat. So it’s okay to watch such fun but no-one is allowed to take part – hypocrisy writ large.
I now was enjoying the thrills I get from dressing en femme, the feel of nylon on my thighs, the cooling breeze stirring my skirt, even my false but firm breasts trusting out of my top. I have greater confidence in my looks, having a reasonably slim figure and have often walked in public dressed, often at the filling station and Lee on Solent seafront
I’d taken to going on a Thursday morning to a local dogging spot, the car park opposite the Royal Armouries at Fort Nelson on Portsdown Hill, Portsmouth. This was the day that the wife went shopping and I could more or less guarantee two or three hours to prepare and have some fun. So, it’s lots of make-up and getting well-dressed to wander round with only some dog-walkers and loads of perves for company. We all know why we’re there, yet so many are nervous and extremely hesitant. Fortunately, there are many who, like me, are either confident or just don’t care. Yes, I’ve been fucked often and almost always get several mouthfuls of cum. I’ve met a couple of other cross-dressers there as well. One, Lesley, is a long-term tranny, doesn’t look, or even try to look, in the least bit feminine but another, Sarah, is convincing. She is a fully committed T-Girl and has lived as a woman since her teens and in my eyes is gorgeous – so much so that I have fucked her a couple of times and, boy, was it fun. Even more fun was when she fucked me! A wonderful surprise and one of, if not the, best fucks I have had. See what you get when you have the confidence to play! I’m really turning into a slut!
My wife regrettably has died of cancer (and I do blame the NHS, my GP in particular, due to their response to Covid) so cuckolding is no longer an option for me.
MMF is the next best thing I suppose but not many Fs willing and available to play it seems. Just a few memories of licking a clit and cock at the same time, then eating the cum out of a soaking cunt. Bliss!
On the plus side I have the house to myself so more opportunities to play.
I also had the opportunity to go, dressed, to a local T-gurls meet at Alwyn’s in his man-cave in the garden. Fully fitted out as a pub with the welcome addition of a pull-out double bed for group entertainment, and private bedrooms for more intimate fun. I’ve met some fantastic gurls there and we’ve all, at one time or another, been fucked by our super-stud host and invited tops. Great meets with the full-range of less-than-convincing to genuine trans gurls. Two in particular, Claire and Nina are actually beautiful!
In July last year I had the great pleasure of a weekend of fun in Liverpool. Four days up North for the Open staying at a Holiday Inn at Albert Docks with easy access and an opportunity for fun that I was unlikely to miss, especially as the weather gave me the excuse to entertain in my room rather than on the course. And entertain I did. Thirteen meets over the four days and what fun I had.
A few other fantasies fulfilled recently as well. I’ve always fancied walking dressed as a “lady of the night” around a lorry park – and I’ve now done that. I’m pleased to say I was invited into a cab in a Fratton lorry park where my miniskirt was removed, I was whipped (I always carry my little flogger in my handbag) and well fucked before having my mouth filled with copious Yorkshire cum! It was so much fun I did it in Southampton too.
On another occasion, on a Saturday night, I was invited to meet someone off Fabguys outside the London Hotel in Southampton. It was really busy and I walked through the partying crowds in my short trench coat and wearing my sexiest stuff – only to find he wasn’t staying there at all, but in the hostel behind for ex-offenders! There were police raiding it at the time. I declined the invite but being jostled in the Saturday party crowd was a massive turn-on.
I’m also fortunate to have experienced many instances of my favourite scenarios – three-and-more-somes! I’ve done this with MMMG, MFM and M,G,G. Guys and gurls, these are great fun and there are many combinations you can get up to.
Is there anything I don’t do? Well, I’ve never seen the fascination for watersports or ***********. Far too messy and requiring a lot of cleaning up afterwards. I did dally with it once with the wife at her request, I think she had a fantasy about, but I think it just ticked a box for her though doing it for her did turn me on.
At my request, most of my meets involve me getting whipped. Why? Well, I’ve found that many, if not most, men secretly get a massive turn-on whipping a peachy arse. On many occasions the whipping session has brough about a premature end to the afternoon as the highly aroused perpetrator of pain found it necessary to quickly finish (often very copiously) in my mouth.
An awful lot of guys fantasise about fucking schoolgirls – and I’m always pleased to oblige. A video I made of this with a very willing volunteer is very popular for some reason lol.
I’m always happy to make videos and role play though not that many guys are willing to show themselves (almost all are married I assume, maybe their wives should keep them happy, or maybe almost every man actually is secretly bisexual!)
Guys, there’s nothing wrong with fantasising. And it’s alright to act out your fantasy – with a willing (and legal) partner.
So, if you’ve read this far then this is me and where I am today. I hope this story encourages you to seize the day, Carpe Diem, like I have. I would so hate to be on my deathbed thinking “I wish I’d…”
Come join me, it’s lovely xxx
Contact me on [email protected] or via xHamster as popeye014
Mike (aka Michaela and Popeye)
vor 4 Jahren
