Fantasy cum true lol

Well I suppose I should start at the beginning as it’s normally the best place lol....

Two weeks ago I was doing my usual past time of seeing what everyone was up to on a favourite site of mine called fabguys when out of the blue I got a message from another user whom I will call Betty, in this message she said she had a female friend who would meet me, she was slim, blonde and would either meet as a female or with a strap on if I desired.

I have to admit I must have read this message about a dozen times and my initial reaction was that it was a wind up as I couldn’t be that lucky...could I ?????

So anyway in the end I replied to Betty saying that a message like that was most definitely a "first" for me but I sure wasn't complaining and again suspecting that it was not genuine I asked Betty what she got out of this possible arrangement?

She replied that she likes to watch if she is available or just to hear about it after the fact from her friend and that really turned her on, again I questioned whether Betty physically got involved and she said she would but was currently away from the UK so she would just enjoy hearing about it afterwards, again I have to admit this started to sound like a wind up especially as Betty had not been on the site very long, only had a few friends and had not been verified as genuine by another user, unfortunately as in all walks of life there are losers everywhere and due to myself being messed around by idiots in the past Betty was getting tarred with the same brush but I am so happy to say that I couldn't have been more wrong :)

So we talked a little more about where this "possible" meet "might" take place and when. The place wasn’t a problem as it was only a few miles from me but of the two possible times I could only do the one which in the end proved not to be a problem. I then went on to enquire if it would be possible for me to dress at the hotel as I haven’t got the bottle to travel dressed, to which the answer was "yes" that’s not a problem.

My next thought was how old is this lady? To which I got an answer which gave me shivers... I have always always loved older mature women and seem to have the same taste in the other sex as well if I am honest and although I will not state the exact age of this lady as there is every possibility she will read this all I will say is she was quite a bit older than me and my god did that set my blood pumping, even before the development of my alter ego of Sienna in the last 18 months or so I have always fantasised about older women and since the introduction of Sienna although I love to be with other similar CD's as myself the fantasy of being Sienna with an older woman has always been at the top of my wish list and to be perfectly honest its one box I thought I would never get to tick.

So I talked a little more with Betty and sorted a couple of minor details out and she said she would talk to her friend whom I will call Carol and come back to me through the fabguys site, this was the Wednesday morning I believe with the possible meet for the following Monday, anyway I heard nothing back from Betty which again made me think it was a wind up and I think it was Friday evening that I sent Betty a message saying that I was assuming by the lack of communication that her friend who was called Carol was not interested, as I thought at this point it was a wind up it felt a little like I was calling Betty's bluff and suspected that I would not get a reply, anyway Saturday morning I woke up and checked my messages and Betty had replied "no, she is interested" please contact her on this email ...@....

Again I looked at the message thinking, is this just the wind up going to next stage or again I am thinking could this actually be real??? God I was so hoping it was but almost didn’t dare think it lol

So I sent Carol an email saying that her friend Betty had been chatting to me and told me to email her, hence this email

To which I got a reply saying again that she would be local to me on the days we discussed and did I have any particular scenarios in mind and did I want to see a picture of her?

Again I have to be honest from the reply I got I was getting a little suspicious and asked her very subtly was this a "service" she provided?? From which I am sure you can work out what I might have been thinking having not had the privilege of meeting the wonderful Carol yet :)

Carol then replied "that I suppose you could call it that butt (pardon the pun) what service would you like me to provide??" and again she said that she asked me before would I like a picture.

To which I replied "that I would love a picture but I was sort of under the impression from Betty that I was helping her out as she had a thing about meeting a CD like myself"

Carol replied "that I was along the right lines, the long and short of it being that she loved sex and she was up in the North East on business and was taking the opportunity while she was away of having some fun" and did I like the picture she had attached???

Well I have done the same myself when I have worked away and "did I" like the picture, you bet I did WOW she was lying on the bed, stocking tops and panties showing but nothing what you may class as rude, oh my good god instant hard on at my end and she looked lovely, very classy and mature mmmmmmmmmmm

She wanted to know what I dress in so I explained that I fully dress, wig and makeup though the makeup is still a work in progress lol and sent her a few pictures of my latest look, short hair and mint green dress.

I didn’t hear anything back from her for quite a few hours and I thought I had blown it she mustn’t have liked what I looked like, bugger lol hey ho that’s life and all that, but no I was wrong I got a reply a few hours later saying she liked my pictures and she was still very interested if I was? If I was????? She had to be k**ding right lol, my heart was pounding just reading the reply and a bit like what it is now typing this and recalling the feeling at the time.
So we had a few more email messages back and forth and I sent her a few more pictures of me, she told me that she had sent one of them to her friend Betty as she particularly loved pictures of "girlies" lifting their skirts and showing their knickers and she knew that would get him all excited which I was more than happy for her to do, also a first for me was that she asked me would it be possible for Betty to ring me, which with a bit of arranging I managed to achieve and we had a 10 minute conversation and where Betty told me a little bit about Carol and that they had been friends for over 20 years and it was obvious that Betty cared a great deal for Carol and I assured her that she would be very safe with me, Betty hoped that we had a wonderful time and would it be possible to take a few pictures and email them to her, to which I replied as long as Carol was ok with that then yes it wasn’t a problem at all, she said that she would if possible like to talk to me again at some point afterwards to hear all the details first hand and again I said that so long as Carol was ok with this then it was fine with me.

Carol also sent me some more pictures of herself, one that was a bit more naughty as a barmaid behind a bar with her boobs out, mmmmm wish I was having a pint in that pub lol and another when she was dressed as a domme

Anyway Monday comes round and Carol wants to know what I was planning on wearing and I told her either my red dress or my new mint green one but I discovered later that my friend Sally managed to get lipstick on that one at our last encounter so I decided on the red one and of course all the accessories to go with it, a gurl has to look the part doesn’t she lol :)

So I am sitting in the hotel car park at the arranged time and ring the number Carol has given me to get her room number, and again to be perfectly honest I was thinking "bet this is a wind up" but thankfully I was very very wrong she answered on the 3rd of 4th ring and gave me her room number and told me to come in.

So I hung up and jumped out of the car and picked my case out of the boot and made my way quite casually into the hotel, I looked quite calm on the outside I think but my heart was going like a jack hammer on the inside. I walked past reception and to the room number I had been given and knocked on the door.

The door opens and I walk in and I see this gorgeous looking lady standing in front of me and I put my case down and she says to me "give me a cuddle" which I am more than happy to oblige and it’s a very good ice breaker as well that first little bit of physical contact can sometimes in my experience be a little uncomfortable but that was definitely not the case here.

She asks me if I could do her a favour and of course I answer that if I can yes not a problem, she asks me if I could take a few photos of her in the dress she is wearing and the a particular pair of shoes to send to her friend Betty as she had bought them for her but not seen her in them yet, which I gladly obliged and we emailed them there and then from my phone, all the time I am taking the photos my face must of looked like a k** let loose in a sweetshop, I am surprised I wasn't drooling, in fact I probably was lol. She was absolutely gorgeous, blonde, slim but not too slim as I prefer real women and legs..... WOW ,I couldn't keep my eyes off them, all the time I am thinking "please be wearing suspenders, please be wearing suspender" lol, I thought I had felt some when we had our first cuddle but wasn’t sure.

Anyway I went off into the bathroom to transform into Sienna and after about 25 mins I look at myself and think well that’s as good as it’s going to get, I feel more nervous meeting this beautiful and lovely lady than I have ever felt meeting another CD with the possible exception of my very first Bi meet but it would be hard to tell which was the most terrifying for me lol
So I walk out of the bathroom and introduce Carol to Sienna and she says "what a transformation" and she seems to like what she sees which I am relieved to hear and she particularly seems to like my dress... oooh this gurl talk is such a turn on I can tell you, I think she then asks me (or it could have been my suggestion) if we could take a couple more pictures of Carol and Sienna to show Betty as she will really really enjoy that and I was more than happy to do this and Carol took one of Sienna on her own as well.

All the David Bailey moments being finished (for now anyway) we stand at the bottom of the bed (me being fully dressed as Sienna) and proceed to start to cuddle each other and start to kiss, OMFG somebody pinch me this is really happening, I can’t believe it, I run my hands over her and as you can guess they head south onto her bum, mmmm that feels lovely and then I can feel the suspender straps, yes, get in, I think to myself lol.

Then I start to nuzzle her neck and she is moaning gently and compliments me on being a good kisser, thanks hun believe me your no slouch yourself and as you can imagine my clitty is rock hard and not that I think it’s possible but seems to be getting harder as Carol touches it through my dress...

To anyone reading this and especially if you’re a CD like me, I have to ask "how jealous are you at this point??"

I am not trying to brag or rub anyone’s nose in it but believe me if I were in your heels and reading this I would be like Kermit the frog I would be that green and there is so much more yet to cum... Including me and Carol lol

We carry on the kissing and fondling and I am having a fantastic time and so is Carol by the sounds of things, she keeps saying things "oh this is so nice", me personally I am having the time of my life but it is so nice to hear that she is enjoying herself too.

After a few subtle attempts to lift her dress so I can get my hands on her bum I give in and become a little less subtle and yank it up over her thighs and I can get at her wonderful arse, excuse my french there but that’s exactly what it was mmmmmm, then she whispers in my ear that she "didn’t put any on as she didn’t think there was any point" and at first I am thinking, what? didn’t put what on then when I move my hand round the front the penny dropped, that was the only thing that did drop mind you, my blood pressure went through the roof as I realised she meant knickers or the lack of, also a very nice surprise to find that she was hairy which is not something I am not personally used to and was a very nice change for me.

She now lifts my dress and takes hold of my clitty and whispers too me "mmmm a lovely hard cock" now there is not much of it but what there is works fine and there is that much blood in there at the minute while it is in her hand I don’t know how I am not fainting lol.

Of course I have to repay the favour and proceed to make my way through the lovely fur to find her clit, which I couldn’t miss as it was quite proud and my god was she wet, I whisper in her ear "that I think she must be liking this" and she replies that "I have no idea" lol, what a lovely wet pussy she has and I am loving the feel of her squirming against my hand though I must say I am doing a fair bit of that myself against hers as well.

She then asks me would I like to unzip her but I am so enjoying that fact that she is fully dressed and I am doing what I am doing to her that I say "in a minute", this might seem strange but it felt so sexy for her still to have her dress on at the time, well I couldn’t hold out too long and eventually I turn her round to get access to the zip and very very slowly unzip her dress, slowly revealing a lovely blue chemise, a gorgeous bum as remember no knickers and tan stocking tops held up by suspenders and she very sexily steps out of the dress and goes and lies down on the bed. At this point I could have happily died there and then as I was already in heaven and when I eventually snapped out of the trance I was in I tried as smoothly as I could but probably failed miserably in my attempt to remove my own dress as sexily as i could and just to be a matching pair I take my knickers off as well. I am wearing my favourite red basque with false boobs, flesh coloured stockings with black tops which are seamed with a bow on the heel and she definitely likes my look and we have a brief conversation about what makes seamed stockings so sexy, mmmmmm seamed stockings I absolutely love them even if they are a pain to get straight and keep straight lol.

So I lie on the bed next to this gorgeous creature, both of us in our underwear and we have a lovely kissing and fondling session and I have to get her boobs out and proceed to suck on her wonderful nipples, I honestly keep waiting for the alarm clock to go off as this all has to be a dream.. doesn’t it??

We then start having a conversation about toys and she asks me did I have any which I do, I have a dildo and she asks me if I had it with me which I did and could she see it, absolutely and her eyes light up as she says mmmm that’s a good size and she says she might use it on me later..... mmmm naughty hee hee

So we are still enjoying exploring each other when my flipping phone rang.... arrrgh well I am supposed to be working lol so I have to answer it... thank god it wasn’t a face time call or the girl at our office would have had a heart attack or died from laughing lol. So I finish the call and I am making my way to the bed and I am thinking god I have to taste that pussy so I stop at the bottom of the bed, work my way up and open her stockinged legs and start to bury my face in that lovely bush with tongue searching for her clitoris, it didn’t take much finding I can tell you and after a minute or two she asks me could I put my dildo in her while I am licking her, hey who am I to say no lol. So I proceed to slowly work my pink dildo into her lovely wet pussy, just a bit of a time and all she can say again and again is "oh this is so lovely" well Carol it’s not exactly unpleasant from where I am either darling lol. After a minute or so I get it all the way in and I am moving it in and out when Carol says just leave it in which I do and turn it 180 degrees to the balls are near her bum so I can get my tongue onto her clit easily. I must have only got my tongue there for 20 or 30 seconds when she says "god... you’re going to make me cum already..." and she proceeds to grip onto me like grim death while the orgasm rushes through her, I am over the moon at this point as my number one aim with anyone I am with is to make sure they have fun before me, I think this comes from being on the small side but I do get a lot of enjoyment out of a partner having an orgasm with me, however it is achieved and I have been told my tongue does have some skill lol

After Carol has caught her breath she asks me would I like to "fuck her" now and my more than happy answer was "if that’s what you would like hun, yes please" she then proceeds to put a condom on me which in itself is quite a sexy experience and then she lifts her gorgeous stockinged legs and puts them over my shoulders and I slowly enter her lovely pussy. My movements are slow and deliberate as much as anything to stop myself from cumming so quickly which with my heightened state of excitement and pleasure was a real possibility if I wasn’t careful. After what I think was a few minutes but could have been 30 seconds lol Carol says "oh god you are so sexy, this is so wonderful I daren’t move as its right on the spot" bloody hell I think, is she going to cum again and as I say to her I might have to pause a little as I will cum soon otherwise she tells me to carry on and I then support myself on my arms still with her legs over my shoulders and kissing her stockinged feet when and playing with her boobs when I can balance lol, then I start to go a little quicker, the only part of me touching her being her legs on my shoulders and my clitty in and out of her fantastic pussy when suddenly I feel her grab my arms quite strongly and ask her is she going to cum again and all she can do is nod and she proceeds to cum again while I am fucking her and closely followed by me....... I know I keep saying this but WOW is all I can think of to describe the feeling, the moment and the occasion.

This in all my adult life is a first for me I have never had a woman reach an orgasm while I was making love to her in that way and to say it was a thrill was somewhat of an understatement.

I climb off her and say "god I could murder a cup of tea" which she gladly makes me and apologises for not having anything stronger which is just as well lol, hee hee I left plenty of lipstick on the cup as well.

Also at some point in the proceedings we take another couple of pictures for Betty both of us just in our underwear, me holding Carols boob and her holding my clitty which Betty apparently loved lol

We then have a lovely cuddle and a nice chat about our own situations which was private and will stay that way, for me the social side of any meet is as important as the fun side, I am definitely not interested in what you may call wham bam thank you maam and just as I was getting wandering hands again as I couldn’t keep my hands off her it became apparent that we were running out of time as she had to meet some colleagues so I had to keep my amorous intentions to myself as the last thing I would want to is make anything awkward for this wonderful person.

So I got changed back to male mode and we have another quick kiss and cuddle and we tell each other that we both enjoyed it and hope to meet again.

I have since had emails with Carol and telephone conversations with Betty and both have confirmed that Carol had a great time when we met and hopes to meet again, if I am interested.... If I am interested, does the phrase wild horses mean anything to you lol

Carol thank you my love for an absolutely wonderful afternoon and for fulfilling my fantasy and thank you Betty for introducing me to Carol and for help in setting things up, I am extremely grateful.

Here’s to next time (I very much hope)

Lots of love
Sienna xxxxx