Losing my Virginity to an Older Woman
Part 1: Spain
This is the story of a journey. It started in Spain, continued in France and finished (climaxed?) in London. It was a journey of discovery. This was when I first discovered the thrill of intimacy with a real woman. This was when I lost my virginity.
This is a completely true story. It happened over 50 years ago but I can remember much of it as if it happened yesterday. (I have used a little “artistic licence” in filling in memory-gaps with actions that probably happened, anyway.) Such things make a big impact on a young mind so I am very grateful that my “teacher” offered such a wonderful experience. Sex has always been great since, mainly I think, because I learned from the start how to offer my partner as much pleasure as I received myself.
I know I was not the first to be initiated by an older woman and I certainly won’t be the last. Joan was probably about twice my age. I was 20. She had married young and she had a son who was older than me, although I never met him. She had been recently divorced. As her son had left home, Joan decided to catch up on her youth and enrolled, as a mature student, in the same London college as me. She was a slim, attractive lady, quite good looking and always smartly dressed. Although it was obvious that she had more money than the rest of us (she owned property for a start) she was always keen to be regarded as one of the crowd. On the whole, she managed this very successfully. She loved nothing better than to join in with the raucous behaviour in our local pub on a Saturday night.
At the time of my story, I had been through two or three “close friendships” with girls. Although I was quite keen to “get into their knickers” I had always respected the word “no”. So, my experience was limited to a bit of titty groping and, on one occasion, a finger exploration of a teen pussy.
One summer, a group of us arranged a holiday in Spain. Seven of us (five males and two females, including Joan) drove out there in two cars with tents and sleeping bags to reduce costs. I can’t recall exactly why, but I went in Joan’s car with the other girl called Sue. Sue was my age, and she was the one I really fancied. But I never managed to get anywhere close. She was keen on somebody else.
On the journey out I recall sharing a (fairly small) tent with the two of them. I wanted to sleep in the middle, but Joan insisted that she should take the middle “to keep us apart”. Nothing happened but, looking back, there were one or two moments when there was a bit of sexual “frisson”. Joan had given me one or two looks which I had been too inexperienced to interpret.
On arrival, we all stayed in a small hotel in a Spanish fishing village (which is probably a major resort now). I shared a room with one of the other guys. Joan and Sue had a room. Dave, who was the driver of the other car and considered the group’s leader, had a room to himself.
Most days were spent lazing around, walking along the coast and doing a little fishing. Every evening was spent in one of the beach bars. On the evening in question, I recall returning to the hotel with Dave and Joan. Dave had drunk a little too much, so Joan and I helped him to his room.
As we got to the room, we all collapsed laughing on the double bed. Dave was on the far side and almost instantly fell into a deep sleep. This left Joan and myself lying next to him on the bed. I don’t know exactly how we managed it, but we had our arms round each other. Up to this point I had not seriously been considering a sexual encounter with her, so I suspect that Joan had manipulated our positions.
At this moment, I most certainly did think about the possibilities that were suddenly offered. This situation appeared to come out of the blue. Or had it? I shall never know for sure, but I believe Joan may have been plotting since earlier in the evening.
Anyway, here was an opportunity too good to miss. Her face was close to mine, so I moved forward to kiss her. She responded eagerly. I have always enjoyed a good “snogging” session and soon we were exploring each other’s mouths with our tongues.
It didn’t take long for my dick to respond in the usual way. I was really enjoying this. And so was Joan. I could feel her body pressing against mine. She was making gentle moaning noises and from time to time she would wriggle as a surge of pleasure passed through her body.
This was most certainly the longest kiss that I had ever had up to that point in my young life. I decided to take a chance. I enjoy all parts of the female body, but in those days I was definitely a tit man. She was wearing a light cotton summer dress. It was yellow with pretty flowers, I recall. I moved my hand and pressed it against one of Joan’s breasts. She reacted by moving her body slightly to give me more room. She was obviously enjoying the attention. Her whole body writhed as I squeezed her breast. All this was done without breaking the kiss.
Then the most unexpected and wonderful thing happened. I felt Joan’s hand reach down and grab my cock outside my shorts. In my past experiences with girls this had never happened. None of my girlfriends had ever taken that sort of initiative. I realised, of course that I was not with a “girl”. This was a woman. A real, horny woman!
We must have broken the kiss at some point. I remember her smile as she reached down with her other hand and started unbuttoning my shorts.
I remembered Dave and looked across. He was completely out of it. I looked at Joan and we both laughed at the circumstances. (I discovered later why Joan had found this situation so humorous. The reason Dave had insisted on a room to himself was because he had wanted to seduce Joan!)
She soon had my buttons undone and reached though to stroke my cock outside my underpants. After a bit of this she grabbed my shorts and pants and started pulling. I lifted my hips slightly and she pulled my clothes down to expose my completely rigid cock.
I remember thinking “What if Dave wakes up?” But then I thought “What the fuck!”
Joan was slowly stroking my dick. It felt fantastic. I felt the need to become more active. So I reached down to her skirt and started pulling it up. She offered help and encouragement by lifting her bottom off the bed. I got her skirt high enough so that I could get my hand inside. I went straight for her panties and started fondling her pubic area. She gasped as I ran a finger up and down her slit. She continued playing with my cock and I pulled her panties to one side and slipped my fingers inside. Her pussy was soaking. Another new experience! The only other cunt I had fingered was not nearly as aroused as this. I slipped a couple of fingers deep into her slit. She gripped my cock firmly and let out a load moan. She was not just playing; she was clearly wanking my cock now.
I had another quick look at Dave, but all was quiet there. I relaxed slightly. I think that was my undoing because, without warning, I suddenly felt the pulses of an oncoming orgasm. Joan must have seen the expression of alarm on my face. I remember her exact words.
“That’s all right, darling. Let it come”, she whispered.
And cum it did. Big jets of spunk came all over her hand, the bed and my shorts. I felt disappointment because I was unable to last longer but on the other hand it had been marvellous. This was the first time another person had helped me ejaculate. The fact that this had come out of the blue, and had been at the hands of a more mature woman, added to the magic of the moment. It was a pity that we had not been sharing a more private space, but that opportunity would come in a few days…
We cleaned up as best we could. I often wonder if Dave ever noticed the stains or the smell!
As we were both sharing rooms with other people, Joan and I never had another chance to get together in the hotel. But I seem to remember that it was almost our last night there anyway.
I know - you are going to say that I had still not lost my virginity. That was true but read on and you will discover what happened on the way home.
Part 2: France
I don’t recall the details, but Sue did not return with us in Joan’s car. I think she might have taken a train to meet up with her family somewhere in Europe.
Anyway, I was understandably quite excited by the thought that I would be spending time alone with Joan. My imagination was taking over – thinking what might occur in my little tent! (I also had an embarrassing “little tent” in my shorts.)
I got a bit of a ribbing from the boys, but I don’t believe anyone suspected what was going on. I was happy to keep the secret as I am not one to boast of success. (Not that I was used to success at that time; but I think you know what I mean.)
Our plan was to take two days to get back to London, staying overnight somewhere in France. Events took over slightly as we had mechanical problems and were delayed in finding somewhere to camp.
It was getting dark when we spotted a nice field. It turned out to be a sports ground. We were heading for a nice patch of secluded grass behind the pavilion when I decided to try the door. It was unlocked. Nobody was around and there was no nearby habitation, so we decided to take our sleeping bags into the changing room.
It was slightly bizarre. There were bits of sticking plaster on the floor and the place had a slight smell of liniment. I didn’t mind at all as we ate the sandwiches that we had bought earlier and then enjoyed a passionate kiss.
I started stroking Joan’s breasts. My word, I was feeling randy. She laughed and said that we should be getting ready for bed. I suggested that it might be warmer if we shared a sleeping bag. She seemed amused by the idea, and we helped each other undress down to our underwear. When I got down to my underpants, she gave my cock a little squeeze. I don’t recall the exact words, but the conversation went something like this:
“That’s a nice piece of meat you have there. I expect a few young ladies have been satisfied by that.”
“Actually, no”, I replied a little sheepishly
“Do you mean you have never had sex before?”
“That’s right”
“My word, a virgin. I am a lucky lady!”
At this point I knew that, at long last, I would be going “the whole way”. The thought was terrifically exciting, and my prick seemed to grow even stiffer.
It was a bit of a struggle getting into the bag, particularly as my cock kept getting in the way. We both laughed but it was nice and cosy when we were in there. (After we realised that we needed to unzip the sleeping bag some of the way.)
I am not sure why we decided to wear underwear because it soon came off. Joan’s bra was the easiest and that did not last long. This was the first time I had been able to fondle a completely naked pair of breasts. We discovered that the most comfortable position in the tight space was “spoon” position with my arms round her, my hands grasping her tits and my prick pushed hard against her bum.
This is when I discovered the “nipple roll”. Her nipples were sticking out like little bullets. I had felt a few breasts before, but this was a new experience. I spent quite a while experimenting. Joan did not mind in the least. She was moving her hips as much as she could in that confined space, pushing her rear end back against my firm cock. This time, there were no inhibitions about noise, and she was not particularly quiet. In fact, she was doing a lot of moaning and groaning and, from time to time, she told me that she liked something and asked me to do it again. When I rolled her nipples between my fingers she gasped and reached down to get hold of my cock.
It was a bit of a struggle, but we eventually managed to remove the remaining items of clothing. (The next day we had a laugh when Joan could not find her knickers. We eventually found them in the bottom of my sleeping bag!)
Still in spoon position, my cock was aching to get inside her. I had a good feel of her cunt and, as before, she was dripping with pussy juice. Then she made a subtle movement with her hips, and we were lined up. It seemed a completely automatic and natural movement as I thrust forward and entered my first vagina.
After a few minutes, she asked me how it felt to be having my first fuck. I told her that it felt like heaven. In actual fact it was somewhat challenging as we did not have complete freedom of movement. She wondered if we would be better off outside the bag but it was getting a bit cool, and I was just enjoying having her warm, naked body close to mine.
She did her best to give me verbal as well as non-verbal encouragement, thrusting back in time to my (somewhat restricted) movements. She took one of my hands away from her breast and placed it over her pubic area. I was unsure what I was supposed to be doing with it, so she explained that she wanted me to stroke her clitoris as we fucked. I wasn’t too sure where the clitoris was so she held a finger and demonstrated how I could give her a little extra pleasure.
For some time, we tried to get a good thrusting rhythm going but it was not easy. After a while I began losing some of my erection and we slowed down our body movements, but I continued playing with her pussy and clit. I soon realised that, as much as I needed release, her need was even greater. She was getting extremely aroused. I had not realised that a lady could become so noisy and uninhibited as she approached her orgasm
“Yes, yes, oh yes,” she kept repeating. “That’s right. Yes. That’s nice. Just like that,” or words to that effect.
I actually forgot about fucking her. My prick had slipped out. I was fascinated by the completely new experience of giving a woman so much pleasure that she could no longer control herself. It was just as well that we were not anywhere that could be overheard.
Finally, she went completely rigid, shouted out one final expletive and fell asleep in my arms. Amazing!
I guess I was no longer, technically, a virgin but I still hadn’t reached the peak of my desires. I still had not ejaculated inside a cunt.
I think we stayed in the same position all night. Another wonderful “first time” experience was waking up next to a naked lady.
Part 3: London
We arrived back at Joan’s flat late the next day. As it was too late to continue with my travel plans, she asked, with a knowing eye and sexy smile, if I wanted to stay the night.
You guessed right. There was no way I was going to refuse that offer! Joan cooked a meal and afterwards we sat on the couch in her living room with a glass of wine each.
After reminiscing about our holiday and the events of the last few days, we started kissing and cuddling. I soon had her tits out and practised my tit-squeezing and nipple-twisting techniques. She encouraged me by telling me what turned her on.
After a while she asked if I would like to suck her breasts. I told her that I would love it. She got on her knees on the sofa and, cupping a hand under one of her boobs, she offered it to my mouth. I took her nipple between my lips and started to apply a little suction. She gasped and squirmed, obviously enjoying the attention.
We must have spent at least half an hour playing with her tits, squeezing, pinching, licking and sucking. I really was in heaven. I was fascinated how I was able to encourage the nipple to get harder and longer. She told me that she wished her previous lovers had paid as much attention to her breasts, as she enjoyed it very much and it got her “turned on below”.
I thought it was about time I investigated “down below”, so I put my hand on her knee and slipped it under her skirt. I stroked her nylons and then reached her stocking tops. I caressed the soft flesh of her thighs as she moved her legs apart. I sucked on a nipple as I explored her suspenders and slipped a hand into her stocking tops.
As I got nearer her panties, I could feel the pussy juices running down her thigh. Then I put my hand over her muff and then started running a finger up and down her slit. She bucked her hips and let out a squeal of delight.
Joan then whispered in my ear. “Let’s go to bed.”
In her bedroom, Joan suggested that I got into bed while she “got ready”. I was a little disappointed because I was anticipating that we would take each other’s clothes off. However, it was still exciting to get into a woman’s bed and wait for her to join me. I wondered if I should keep my underpants on but decided I would wait for her naked. I lay between her crispy clean sheets slowly stroking a massive hard-on.
When she came into the room, she was wearing a flimsy black creation. She looked ravishing, her tits and bush being clearly visible through the sheer nylon. If possible, my cock got even stiffer at the sight.
This is a moment that I recall vividly. She smiled and pulled back the covers to join me in bed. She noticed my member and feigned a look of surprise.
“My word, look what you have for me!” She climbed in and wrapped her arms and legs round me. This was the moment I had been waiting for. Our previous sexy encounters had been fun, but this was the real thing.
We spent a while kissing, stroking and fondling each other. Her tits felt particularly sexy when I squeezed them through her negligee.
Then Joan started kissing my body. She sucked my nipples and then moved her lips down my body: over my stomach and down to my pubic area. Then I felt a surge of pleasure when her mouth touched my cock. This was another “first” for me. I had read about fellatio and tried to imagine what it would be like. In fact, oral sex appeared frequently in my masturbatory fantasies.
The feeling, as she took the whole of my tool into her mouth, was indescribable. This was even better than I had imagined. She stroked, licked and sucked me for some time. I then thought that I should return the compliment. I lifted her negligee and started moving my lips and tongue down her body as she had done to me. When I approached my goal, Joan opened her legs in invitation.
I stroked her bushy pubes and ran a finger up and down her slit. It was dark under the bedding, and I wanted to see what I was doing so I tried to get the covers off. She realised what I was doing and helped by removing the sheets.
She spread her legs wide so that I could inspect her cunt in all its glory. This was the first time that I had got my face really close to a pussy. I will never forget the smell. The thought of it still turns me on. It was quite strong but certainly not unpleasant; sort of musky but sweet at the same time. I gazed at her pink and swollen pussy lips. She twitched as I explored her most secret spot with my fingers, running them up and down her slit and slightly parting her labia. She was wet with her slightly sticky juices. I pulled her cunt lips apart and found the clitoris that I had stroked in France. This was a real education!
It seemed to be completely natural to want to taste her, so I put my face in close and placed my tongue against her cunt. She gave a little squeal of pleasure as I licked a woman for the first time. Again, I was surprised to find the taste, although quite strong, rather likeable. What was really exciting was the knowledge that a grown woman was allowing me this most intimate action. Also, I was turned-on by the clear indications that she was getting as much pleasure from this oral attention as I had done a little earlier. I licked the whole length of her pussy and then thrust my tongue as deep as I could into her slit. Joan gave a sigh and I remember her whispering “Oh, yes” several times.
I was bent slightly awkwardly so I moved to a slightly more comfortable position which put my hips near her face. She took the hint, and I soon felt her lips wrapped around my prick. This was the classic “69” that I had heard about.
What a thrill it was to be able to pleasure each other in this way. I spent quite a while exploring her gash with my tongue and fingers whilst she sucked and licked my rock-hard cock.
We tried several different variations on the theme. First, I went on top with my knees either side of her head. I thrust my face into her pussy whilst she held my cock and fed it to her mouth. I rather liked it when, later, she got on top of me, placed her lips round my cock end positioned her hips so that I had full access to her cunt. Since then, I have always been thrilled when a woman indicates, by her movements and body position, what she wants me to do to excite her.
I am also excited when a woman uses explicit words to explain what she wants.
“Let’s fuck,” said Joan. This was the first time that I had heard a woman use the f-word. That was a turn-on in its own right. And the thought of entering her almost made me cum immediately.
We turned face-to-face and kissed. I told her that it had been my first experience of oral sex. She acted surprised saying that I was so good she thought I had been doing it for years!
Joan laid on her back and I climbed on in the classic missionary position with her legs wide apart. My cock felt as if it would explode but I managed to control myself as she reached down and guided me into her. She controlled me gently with her hands, running the tip of my dick up and down her soaking pussy, getting plenty of her sex-juices onto my manhood.
When I felt that she had positioned me where she wanted me, I gave a thrust and my cock slipped easily into her cunt, right up to the hilt. What a wonderful feeling! Although I had penetrated her when we had been in our sleeping bag, this was quite different. This time I was so deep that our pubic hairs were in close contact. I had that strange, empowering moment of feeling completely inside a woman. What was particularly thrilling was that she wanted me inside her and was getting as much excitement as I was.
As I began thrusting, she started moving her hips to match my movements. She wrapped her arms round me and pulled me closer to her breasts as we kissed, tongues exploring each other’s mouths. Then she lifted her legs and put her feet over my shoulders. This meant that I penetrated her even deeper.
“Oh, yes” she sighed. The look on her face indicated that I was doing OK.
I raised my body slightly and looked down. I was thrilled by the amazing sight of my cock sliding in and out of a lovely lady’s pussy. This was just too exciting. I felt myself rushing towards my first orgasm inside a woman.
I think she sensed that I was on the brink.
I remember her exact words. “Yes. Fuck me! Give me all you’ve got!”
That did it. I started tingling from the tips of my toes and suddenly my prick was throbbing, and I was jetting streams of spunk deep inside her.
“That’s it, darling. Let it all come out,” she said, encouragingly.
I didn’t need any encouragement as waves of sheer pleasure swept from my balls to the tip of my cock.
It seemed to continue for ages but eventually I completed my orgasm and collapsed on top of her. I think we both went to sleep soon after, completely satisfied after hours (even days!) of sexual tension.
It had taken quite a while, and quite a journey, but eventually I had reached full manhood and achieved my goal of spunking inside a woman.
That completes my story of lost virginity. Do you have anything as exciting?
Afterthoughts
1. Some of you are no doubt wondering why I was still a virgin at 20. There are a number of reasons. Pre-marital sex was not as widespread as it is now, and “young ladies” were often expected to wait until marriage. Contraception was also more of an issue. (Joan used a diaphragm.) It turns out that none of the girls that I happened to come across (before Joan) were comfortable about “going all the way”. Although many guys would have ignored this, it was important to me that any woman I had sex with was as eager to fuck me as I was to fuck them. It’s called “respect”. Plus, it’s much more fun!
2. Memory is a funny thing. I have always had lasting memories of some of the events in this story: our first kiss, the feel of her hand on my cock for the first time, the bizarre location of my first fuck, bringing her off and so on. But other parts of the story came back to me as I started writing. For example, I had completely forgotten that we were in the “spoon” position in the sleeping bag. I was writing about the problems of the bag when I suddenly remembered how we resolved them.
3. I don’t know about you, but I know that my first real adventures into sex were a big influence on my preferences and desires. Following my youthful experiences with Joan and Julie (“My Helpful Landlady”) I am still attracted to women in their thirties and forties. (They are called milfs now.) Sexy lingerie, especially stockings and suspenders, really turn me on. I love the slow build up with plenty of foreplay (kissing, fondling, mutual masturbation, oral…). Most of all, I love it when two (or more) people are comfortable enough to be able to explore their, and their partners, sexuality without any inhibitions.
This is the story of a journey. It started in Spain, continued in France and finished (climaxed?) in London. It was a journey of discovery. This was when I first discovered the thrill of intimacy with a real woman. This was when I lost my virginity.
This is a completely true story. It happened over 50 years ago but I can remember much of it as if it happened yesterday. (I have used a little “artistic licence” in filling in memory-gaps with actions that probably happened, anyway.) Such things make a big impact on a young mind so I am very grateful that my “teacher” offered such a wonderful experience. Sex has always been great since, mainly I think, because I learned from the start how to offer my partner as much pleasure as I received myself.
I know I was not the first to be initiated by an older woman and I certainly won’t be the last. Joan was probably about twice my age. I was 20. She had married young and she had a son who was older than me, although I never met him. She had been recently divorced. As her son had left home, Joan decided to catch up on her youth and enrolled, as a mature student, in the same London college as me. She was a slim, attractive lady, quite good looking and always smartly dressed. Although it was obvious that she had more money than the rest of us (she owned property for a start) she was always keen to be regarded as one of the crowd. On the whole, she managed this very successfully. She loved nothing better than to join in with the raucous behaviour in our local pub on a Saturday night.
At the time of my story, I had been through two or three “close friendships” with girls. Although I was quite keen to “get into their knickers” I had always respected the word “no”. So, my experience was limited to a bit of titty groping and, on one occasion, a finger exploration of a teen pussy.
One summer, a group of us arranged a holiday in Spain. Seven of us (five males and two females, including Joan) drove out there in two cars with tents and sleeping bags to reduce costs. I can’t recall exactly why, but I went in Joan’s car with the other girl called Sue. Sue was my age, and she was the one I really fancied. But I never managed to get anywhere close. She was keen on somebody else.
On the journey out I recall sharing a (fairly small) tent with the two of them. I wanted to sleep in the middle, but Joan insisted that she should take the middle “to keep us apart”. Nothing happened but, looking back, there were one or two moments when there was a bit of sexual “frisson”. Joan had given me one or two looks which I had been too inexperienced to interpret.
On arrival, we all stayed in a small hotel in a Spanish fishing village (which is probably a major resort now). I shared a room with one of the other guys. Joan and Sue had a room. Dave, who was the driver of the other car and considered the group’s leader, had a room to himself.
Most days were spent lazing around, walking along the coast and doing a little fishing. Every evening was spent in one of the beach bars. On the evening in question, I recall returning to the hotel with Dave and Joan. Dave had drunk a little too much, so Joan and I helped him to his room.
As we got to the room, we all collapsed laughing on the double bed. Dave was on the far side and almost instantly fell into a deep sleep. This left Joan and myself lying next to him on the bed. I don’t know exactly how we managed it, but we had our arms round each other. Up to this point I had not seriously been considering a sexual encounter with her, so I suspect that Joan had manipulated our positions.
At this moment, I most certainly did think about the possibilities that were suddenly offered. This situation appeared to come out of the blue. Or had it? I shall never know for sure, but I believe Joan may have been plotting since earlier in the evening.
Anyway, here was an opportunity too good to miss. Her face was close to mine, so I moved forward to kiss her. She responded eagerly. I have always enjoyed a good “snogging” session and soon we were exploring each other’s mouths with our tongues.
It didn’t take long for my dick to respond in the usual way. I was really enjoying this. And so was Joan. I could feel her body pressing against mine. She was making gentle moaning noises and from time to time she would wriggle as a surge of pleasure passed through her body.
This was most certainly the longest kiss that I had ever had up to that point in my young life. I decided to take a chance. I enjoy all parts of the female body, but in those days I was definitely a tit man. She was wearing a light cotton summer dress. It was yellow with pretty flowers, I recall. I moved my hand and pressed it against one of Joan’s breasts. She reacted by moving her body slightly to give me more room. She was obviously enjoying the attention. Her whole body writhed as I squeezed her breast. All this was done without breaking the kiss.
Then the most unexpected and wonderful thing happened. I felt Joan’s hand reach down and grab my cock outside my shorts. In my past experiences with girls this had never happened. None of my girlfriends had ever taken that sort of initiative. I realised, of course that I was not with a “girl”. This was a woman. A real, horny woman!
We must have broken the kiss at some point. I remember her smile as she reached down with her other hand and started unbuttoning my shorts.
I remembered Dave and looked across. He was completely out of it. I looked at Joan and we both laughed at the circumstances. (I discovered later why Joan had found this situation so humorous. The reason Dave had insisted on a room to himself was because he had wanted to seduce Joan!)
She soon had my buttons undone and reached though to stroke my cock outside my underpants. After a bit of this she grabbed my shorts and pants and started pulling. I lifted my hips slightly and she pulled my clothes down to expose my completely rigid cock.
I remember thinking “What if Dave wakes up?” But then I thought “What the fuck!”
Joan was slowly stroking my dick. It felt fantastic. I felt the need to become more active. So I reached down to her skirt and started pulling it up. She offered help and encouragement by lifting her bottom off the bed. I got her skirt high enough so that I could get my hand inside. I went straight for her panties and started fondling her pubic area. She gasped as I ran a finger up and down her slit. She continued playing with my cock and I pulled her panties to one side and slipped my fingers inside. Her pussy was soaking. Another new experience! The only other cunt I had fingered was not nearly as aroused as this. I slipped a couple of fingers deep into her slit. She gripped my cock firmly and let out a load moan. She was not just playing; she was clearly wanking my cock now.
I had another quick look at Dave, but all was quiet there. I relaxed slightly. I think that was my undoing because, without warning, I suddenly felt the pulses of an oncoming orgasm. Joan must have seen the expression of alarm on my face. I remember her exact words.
“That’s all right, darling. Let it come”, she whispered.
And cum it did. Big jets of spunk came all over her hand, the bed and my shorts. I felt disappointment because I was unable to last longer but on the other hand it had been marvellous. This was the first time another person had helped me ejaculate. The fact that this had come out of the blue, and had been at the hands of a more mature woman, added to the magic of the moment. It was a pity that we had not been sharing a more private space, but that opportunity would come in a few days…
We cleaned up as best we could. I often wonder if Dave ever noticed the stains or the smell!
As we were both sharing rooms with other people, Joan and I never had another chance to get together in the hotel. But I seem to remember that it was almost our last night there anyway.
I know - you are going to say that I had still not lost my virginity. That was true but read on and you will discover what happened on the way home.
Part 2: France
I don’t recall the details, but Sue did not return with us in Joan’s car. I think she might have taken a train to meet up with her family somewhere in Europe.
Anyway, I was understandably quite excited by the thought that I would be spending time alone with Joan. My imagination was taking over – thinking what might occur in my little tent! (I also had an embarrassing “little tent” in my shorts.)
I got a bit of a ribbing from the boys, but I don’t believe anyone suspected what was going on. I was happy to keep the secret as I am not one to boast of success. (Not that I was used to success at that time; but I think you know what I mean.)
Our plan was to take two days to get back to London, staying overnight somewhere in France. Events took over slightly as we had mechanical problems and were delayed in finding somewhere to camp.
It was getting dark when we spotted a nice field. It turned out to be a sports ground. We were heading for a nice patch of secluded grass behind the pavilion when I decided to try the door. It was unlocked. Nobody was around and there was no nearby habitation, so we decided to take our sleeping bags into the changing room.
It was slightly bizarre. There were bits of sticking plaster on the floor and the place had a slight smell of liniment. I didn’t mind at all as we ate the sandwiches that we had bought earlier and then enjoyed a passionate kiss.
I started stroking Joan’s breasts. My word, I was feeling randy. She laughed and said that we should be getting ready for bed. I suggested that it might be warmer if we shared a sleeping bag. She seemed amused by the idea, and we helped each other undress down to our underwear. When I got down to my underpants, she gave my cock a little squeeze. I don’t recall the exact words, but the conversation went something like this:
“That’s a nice piece of meat you have there. I expect a few young ladies have been satisfied by that.”
“Actually, no”, I replied a little sheepishly
“Do you mean you have never had sex before?”
“That’s right”
“My word, a virgin. I am a lucky lady!”
At this point I knew that, at long last, I would be going “the whole way”. The thought was terrifically exciting, and my prick seemed to grow even stiffer.
It was a bit of a struggle getting into the bag, particularly as my cock kept getting in the way. We both laughed but it was nice and cosy when we were in there. (After we realised that we needed to unzip the sleeping bag some of the way.)
I am not sure why we decided to wear underwear because it soon came off. Joan’s bra was the easiest and that did not last long. This was the first time I had been able to fondle a completely naked pair of breasts. We discovered that the most comfortable position in the tight space was “spoon” position with my arms round her, my hands grasping her tits and my prick pushed hard against her bum.
This is when I discovered the “nipple roll”. Her nipples were sticking out like little bullets. I had felt a few breasts before, but this was a new experience. I spent quite a while experimenting. Joan did not mind in the least. She was moving her hips as much as she could in that confined space, pushing her rear end back against my firm cock. This time, there were no inhibitions about noise, and she was not particularly quiet. In fact, she was doing a lot of moaning and groaning and, from time to time, she told me that she liked something and asked me to do it again. When I rolled her nipples between my fingers she gasped and reached down to get hold of my cock.
It was a bit of a struggle, but we eventually managed to remove the remaining items of clothing. (The next day we had a laugh when Joan could not find her knickers. We eventually found them in the bottom of my sleeping bag!)
Still in spoon position, my cock was aching to get inside her. I had a good feel of her cunt and, as before, she was dripping with pussy juice. Then she made a subtle movement with her hips, and we were lined up. It seemed a completely automatic and natural movement as I thrust forward and entered my first vagina.
After a few minutes, she asked me how it felt to be having my first fuck. I told her that it felt like heaven. In actual fact it was somewhat challenging as we did not have complete freedom of movement. She wondered if we would be better off outside the bag but it was getting a bit cool, and I was just enjoying having her warm, naked body close to mine.
She did her best to give me verbal as well as non-verbal encouragement, thrusting back in time to my (somewhat restricted) movements. She took one of my hands away from her breast and placed it over her pubic area. I was unsure what I was supposed to be doing with it, so she explained that she wanted me to stroke her clitoris as we fucked. I wasn’t too sure where the clitoris was so she held a finger and demonstrated how I could give her a little extra pleasure.
For some time, we tried to get a good thrusting rhythm going but it was not easy. After a while I began losing some of my erection and we slowed down our body movements, but I continued playing with her pussy and clit. I soon realised that, as much as I needed release, her need was even greater. She was getting extremely aroused. I had not realised that a lady could become so noisy and uninhibited as she approached her orgasm
“Yes, yes, oh yes,” she kept repeating. “That’s right. Yes. That’s nice. Just like that,” or words to that effect.
I actually forgot about fucking her. My prick had slipped out. I was fascinated by the completely new experience of giving a woman so much pleasure that she could no longer control herself. It was just as well that we were not anywhere that could be overheard.
Finally, she went completely rigid, shouted out one final expletive and fell asleep in my arms. Amazing!
I guess I was no longer, technically, a virgin but I still hadn’t reached the peak of my desires. I still had not ejaculated inside a cunt.
I think we stayed in the same position all night. Another wonderful “first time” experience was waking up next to a naked lady.
Part 3: London
We arrived back at Joan’s flat late the next day. As it was too late to continue with my travel plans, she asked, with a knowing eye and sexy smile, if I wanted to stay the night.
You guessed right. There was no way I was going to refuse that offer! Joan cooked a meal and afterwards we sat on the couch in her living room with a glass of wine each.
After reminiscing about our holiday and the events of the last few days, we started kissing and cuddling. I soon had her tits out and practised my tit-squeezing and nipple-twisting techniques. She encouraged me by telling me what turned her on.
After a while she asked if I would like to suck her breasts. I told her that I would love it. She got on her knees on the sofa and, cupping a hand under one of her boobs, she offered it to my mouth. I took her nipple between my lips and started to apply a little suction. She gasped and squirmed, obviously enjoying the attention.
We must have spent at least half an hour playing with her tits, squeezing, pinching, licking and sucking. I really was in heaven. I was fascinated how I was able to encourage the nipple to get harder and longer. She told me that she wished her previous lovers had paid as much attention to her breasts, as she enjoyed it very much and it got her “turned on below”.
I thought it was about time I investigated “down below”, so I put my hand on her knee and slipped it under her skirt. I stroked her nylons and then reached her stocking tops. I caressed the soft flesh of her thighs as she moved her legs apart. I sucked on a nipple as I explored her suspenders and slipped a hand into her stocking tops.
As I got nearer her panties, I could feel the pussy juices running down her thigh. Then I put my hand over her muff and then started running a finger up and down her slit. She bucked her hips and let out a squeal of delight.
Joan then whispered in my ear. “Let’s go to bed.”
In her bedroom, Joan suggested that I got into bed while she “got ready”. I was a little disappointed because I was anticipating that we would take each other’s clothes off. However, it was still exciting to get into a woman’s bed and wait for her to join me. I wondered if I should keep my underpants on but decided I would wait for her naked. I lay between her crispy clean sheets slowly stroking a massive hard-on.
When she came into the room, she was wearing a flimsy black creation. She looked ravishing, her tits and bush being clearly visible through the sheer nylon. If possible, my cock got even stiffer at the sight.
This is a moment that I recall vividly. She smiled and pulled back the covers to join me in bed. She noticed my member and feigned a look of surprise.
“My word, look what you have for me!” She climbed in and wrapped her arms and legs round me. This was the moment I had been waiting for. Our previous sexy encounters had been fun, but this was the real thing.
We spent a while kissing, stroking and fondling each other. Her tits felt particularly sexy when I squeezed them through her negligee.
Then Joan started kissing my body. She sucked my nipples and then moved her lips down my body: over my stomach and down to my pubic area. Then I felt a surge of pleasure when her mouth touched my cock. This was another “first” for me. I had read about fellatio and tried to imagine what it would be like. In fact, oral sex appeared frequently in my masturbatory fantasies.
The feeling, as she took the whole of my tool into her mouth, was indescribable. This was even better than I had imagined. She stroked, licked and sucked me for some time. I then thought that I should return the compliment. I lifted her negligee and started moving my lips and tongue down her body as she had done to me. When I approached my goal, Joan opened her legs in invitation.
I stroked her bushy pubes and ran a finger up and down her slit. It was dark under the bedding, and I wanted to see what I was doing so I tried to get the covers off. She realised what I was doing and helped by removing the sheets.
She spread her legs wide so that I could inspect her cunt in all its glory. This was the first time that I had got my face really close to a pussy. I will never forget the smell. The thought of it still turns me on. It was quite strong but certainly not unpleasant; sort of musky but sweet at the same time. I gazed at her pink and swollen pussy lips. She twitched as I explored her most secret spot with my fingers, running them up and down her slit and slightly parting her labia. She was wet with her slightly sticky juices. I pulled her cunt lips apart and found the clitoris that I had stroked in France. This was a real education!
It seemed to be completely natural to want to taste her, so I put my face in close and placed my tongue against her cunt. She gave a little squeal of pleasure as I licked a woman for the first time. Again, I was surprised to find the taste, although quite strong, rather likeable. What was really exciting was the knowledge that a grown woman was allowing me this most intimate action. Also, I was turned-on by the clear indications that she was getting as much pleasure from this oral attention as I had done a little earlier. I licked the whole length of her pussy and then thrust my tongue as deep as I could into her slit. Joan gave a sigh and I remember her whispering “Oh, yes” several times.
I was bent slightly awkwardly so I moved to a slightly more comfortable position which put my hips near her face. She took the hint, and I soon felt her lips wrapped around my prick. This was the classic “69” that I had heard about.
What a thrill it was to be able to pleasure each other in this way. I spent quite a while exploring her gash with my tongue and fingers whilst she sucked and licked my rock-hard cock.
We tried several different variations on the theme. First, I went on top with my knees either side of her head. I thrust my face into her pussy whilst she held my cock and fed it to her mouth. I rather liked it when, later, she got on top of me, placed her lips round my cock end positioned her hips so that I had full access to her cunt. Since then, I have always been thrilled when a woman indicates, by her movements and body position, what she wants me to do to excite her.
I am also excited when a woman uses explicit words to explain what she wants.
“Let’s fuck,” said Joan. This was the first time that I had heard a woman use the f-word. That was a turn-on in its own right. And the thought of entering her almost made me cum immediately.
We turned face-to-face and kissed. I told her that it had been my first experience of oral sex. She acted surprised saying that I was so good she thought I had been doing it for years!
Joan laid on her back and I climbed on in the classic missionary position with her legs wide apart. My cock felt as if it would explode but I managed to control myself as she reached down and guided me into her. She controlled me gently with her hands, running the tip of my dick up and down her soaking pussy, getting plenty of her sex-juices onto my manhood.
When I felt that she had positioned me where she wanted me, I gave a thrust and my cock slipped easily into her cunt, right up to the hilt. What a wonderful feeling! Although I had penetrated her when we had been in our sleeping bag, this was quite different. This time I was so deep that our pubic hairs were in close contact. I had that strange, empowering moment of feeling completely inside a woman. What was particularly thrilling was that she wanted me inside her and was getting as much excitement as I was.
As I began thrusting, she started moving her hips to match my movements. She wrapped her arms round me and pulled me closer to her breasts as we kissed, tongues exploring each other’s mouths. Then she lifted her legs and put her feet over my shoulders. This meant that I penetrated her even deeper.
“Oh, yes” she sighed. The look on her face indicated that I was doing OK.
I raised my body slightly and looked down. I was thrilled by the amazing sight of my cock sliding in and out of a lovely lady’s pussy. This was just too exciting. I felt myself rushing towards my first orgasm inside a woman.
I think she sensed that I was on the brink.
I remember her exact words. “Yes. Fuck me! Give me all you’ve got!”
That did it. I started tingling from the tips of my toes and suddenly my prick was throbbing, and I was jetting streams of spunk deep inside her.
“That’s it, darling. Let it all come out,” she said, encouragingly.
I didn’t need any encouragement as waves of sheer pleasure swept from my balls to the tip of my cock.
It seemed to continue for ages but eventually I completed my orgasm and collapsed on top of her. I think we both went to sleep soon after, completely satisfied after hours (even days!) of sexual tension.
It had taken quite a while, and quite a journey, but eventually I had reached full manhood and achieved my goal of spunking inside a woman.
That completes my story of lost virginity. Do you have anything as exciting?
Afterthoughts
1. Some of you are no doubt wondering why I was still a virgin at 20. There are a number of reasons. Pre-marital sex was not as widespread as it is now, and “young ladies” were often expected to wait until marriage. Contraception was also more of an issue. (Joan used a diaphragm.) It turns out that none of the girls that I happened to come across (before Joan) were comfortable about “going all the way”. Although many guys would have ignored this, it was important to me that any woman I had sex with was as eager to fuck me as I was to fuck them. It’s called “respect”. Plus, it’s much more fun!
2. Memory is a funny thing. I have always had lasting memories of some of the events in this story: our first kiss, the feel of her hand on my cock for the first time, the bizarre location of my first fuck, bringing her off and so on. But other parts of the story came back to me as I started writing. For example, I had completely forgotten that we were in the “spoon” position in the sleeping bag. I was writing about the problems of the bag when I suddenly remembered how we resolved them.
3. I don’t know about you, but I know that my first real adventures into sex were a big influence on my preferences and desires. Following my youthful experiences with Joan and Julie (“My Helpful Landlady”) I am still attracted to women in their thirties and forties. (They are called milfs now.) Sexy lingerie, especially stockings and suspenders, really turn me on. I love the slow build up with plenty of foreplay (kissing, fondling, mutual masturbation, oral…). Most of all, I love it when two (or more) people are comfortable enough to be able to explore their, and their partners, sexuality without any inhibitions.
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