Written by Jason

19 Nov 2017

Part 1 of my story (How I lost my virginity) was written a couple of weeks ago, on a lonely evening while I was staying at my parent’s house. It is now 20 years since the lovely MILF next door broke my duck and a lot has happened since then, 2 failed marriages (I still haven’t worked out what makes a happy marriage, but perhaps I just haven’t met the right woman) and I now work for a different DIY chain as manager of one of their flagship stores. Both my parents have died within the last 3 years, my mother from cancer 3 years ago, and my father from a massive heart attack 6 months ago.

I was staying at my parent’s house for a few days to try to sort a few things out. I am an only child, so their house will come to me when it’s all sorted, but I don’t need money so I’m not in any hurry. In truth, I quite enjoy staying here, so I have found a local guy to come round and do the garden once a week, and I am effectively using the place as a holiday home. It was thinking of Cynthia living next door that prompted me to write the first part. A lot has happened in her life since she took my cherry, she divorced her husband Harry about 10 years ago when she discovered he was having an affair with his secretary at his haulage company. It seems not all of his golfing weekends away were spent on the golf course. Harry had worked so hard to build up his business, and Cynthia had taken him to the cleaners in the divorce settlement, ending up with the house and quite a large cash settlement. I knew that my parents had remained friendly with Cynthia after her divorce, but other than that, I was not too involved as I was living and working away.

One afternoon when I was cutting the grass to try to keep the garden tidy, Cynthia wandered over to say Hi. She said she had left me to my own devices because she didn’t know how I was feeling after my father’s death, but I said I was fine and would she like to come in for a cup of tea. I had not seen Cynthia for several years, so it was nice to sit at the breakfast bar in the kitchen with a cup of tea and catch up. From 20 years ago, I remembered Cynthia as a MILF that I really had the hots for, losing my virginity to her had been such an experience, but the opportunity for a repeat with her had just not materialised. 20 years on and Cynthia is a very attractive mid-60’s lady who appears to have lost weight as I gather she has a very active fitness regime at the gym, and she still has those gorgeous tits which any woman half her age would die for.

She said her daughter, Sally, now worked as a GP in a town close-by (which I knew about) but she had recently split with her husband, which I was not aware of. She didn’t explain the reason for the split and I didn’t think I should pry. She did, however, seem to want to talk more about Sally and I got the impression she was trying to set me up for a date with her daughter, but I said it was in the past, history that was best left there.

By this stage, our conversation had become quite light-hearted, the memories of my parents’ deaths being set to one side for now. Cynthia asked me if I remembered the incident 20-odd years ago when she asked me to come round to her house to solve her electrical problem, I said how could I ever forget it, as it had been the most wonderful sex I had experienced, then or since. She then said she had actually switched off the circuit breaker deliberately and I said I had suspected that at the time. She became a little pensive, then asked “did you mean what you said about wonderful sex 20 years ago?” to which I replied “of course, I remember vividly you saying there was going to be another time for us, but I was gutted it never happened”. She then surprised me by saying “well, if I can’t set you up with a date with Sally, how about a repeat with me?”

All of a sudden, we were in each other’s arms kissing each other and wanting to become passionate. I think we were both remembering our coupling 20 years ago, and longing for the repeat that had never happened. I managed to get inside her blouse, and thence her bra, so I could explore those beautiful tits. Cynthia had the front of my trousers open and managed to extract my penis, which was rapidly becoming erect. She knelt down in front of me and enveloped my cock in her mouth. I didn’t want a quick fuck across the dining table, so I pulled her to her feet and said “upstairs …… now” in a very masterly fashion. We almost ran up the stairs, discarding clothing as we went, I was sleeping in my old bedroom, which had only a single bed, so we ended up in my parents’ bed.

After quite a short foreplay, I fucked Cynthia with great passion and a great deal of grunting, gasping and expressions of joy. When I bathed her cervix with my sperm, she was gasping and demanding that I give her more. The generational gap between us didn’t seem to matter as we both enjoyed each other’s bodies. We stayed in bed for several hours and I eventually managed to fuck her again, adding to my earlier deposits. She said I had made an awful mess of her pussy and a real gentleman would clean her up. Needless to say, I did just that, making her orgasm again so powerfully it was well worth the mess she made on my face, she was after all simply returning the mess I made in her pussy.

As we lay there afterwards, Cynthia confided that she and my mother had shared my father’s affections for many years after her divorce. It would seem that my Dad had a high sex drive, so it suited my Mum if her very good friend next door helped her keep him satisfied. He would go round to Cynthia’s house at least twice a week to ‘give her a good seeing to’ as she put it, so going to bed with me had brought back many happy memories. My father had, in fact, fucked her in that very bed just a couple of days before his death. She said the doctor had told her it had nothing to do with his death, he had a ticking time bomb that could have gone off any time. I said he had clearly died happy, which was how I was feeling now.

Cynthia persisted in talking about her daughter and, in the circumstances, I didn’t think I could say no abruptly. Eventually, I conceded that I would perhaps meet Sally for a drink another time when I was staying at the house. My memory of Sally was clouded by the recollection of our one and only disastrous date, and her frosty attitude towards me since then.

Having been to bed with her, it seemed appropriate to exchange mobile numbers with Cynthia, and I began talking to her on the phone quite often. A week or so later, she phoned me to ask if I was going down to the house the following weekend and, when I said maybe, she said that she had tentatively set me up for a date with Sally, a drink in a local pub at lunchtime on Saturday.

When we met, I was quite surprised that I found Sally quite attractive, about my height, 5’ 9”, slim with medium length fair hair, not much of a bust, but then nothing could match up to her mother’s lovely tits. She wears glasses now, which I thought made her look quite studious, I could easily imagine her looking over her glasses in her consulting room telling me I should look after my health, but maybe I have a secret wish to be dominated by a woman. We chatted about our lives over the past 20 years, and I was relieved she did not mention our disastrous date in the local cinema.

We had chatted for over an hour, and I suggested we could have a meal together at a local restaurant in the evening to continue the conversation. Sally agreed, so I phoned the restaurant to book a table before we parted. I went back to the house to catch up on the cleaning, having such a large holiday home was a bit of a pain as there was so much to keep clean.

We met at the restaurant at 7.30 pm as arranged and basically picked up the conversation where we left off, only this time I found myself telling Sally a lot more about my past. She asked why neither of my marriages had lasted, and eventually I admitted it was down to lack of commitment on my part. I asked her about her husband and she said he wanted children and she didn’t, she loved her job so much and didn’t want her own children getting in the way of that.

The bottle of wine we drank with the meal had somehow stretched to a second bottle and, by the time we finished, Sally said she was concerned about driving home, which was close to her surgery about 10 miles away. She said her car would be safe in the open-air carpark close to the police station, so perhaps she would ask her Mum to put her up for the night. I had walked the half mile or so distance to the restaurant and, as it was still dry and reasonably warm, I suggested we could walk back.

Shortly after we left the restaurant, Sally linked arms with me, and I was quite enjoying the feeling of her body rubbing against mine. We continued chatting and, as we turned the corner at the end of my street, she suddenly said “but what if Mum is entertaining a gentleman tonight …… that would be so embarrassing”. It crossed my mind to ask whether she knew whether her mother was in the habit of entertaining gentlemen, but decided it was better to seize my opportunity and I said she was welcome to stay at my house if she wanted. She reached over to kiss me on the cheek and said that would save her from a difficult situation with her Mum.

As we walked through the front door, Sally turned to me and said “does this mean we are going to end up in bed together?” Walking back to the house rubbing hips with Sally had got me feeling quite horny, but I felt I should not try to take advantage of the situation, and I was about to say ‘of course not’ when Sally pre-empted me by saying “oh I do hope so”. There was a brief pause while we both adapted to the same wavelength, and we fell into each other’s arms, kissing each other passionately, which quickly developed into mauling each other’s bodies through our clothes. Coats were quickly removed and dropped on the floor in the hall, and I was quite surprised that Sally was keen to get inside my other clothes, so I thought I should follow suit.

We rushed upstairs like a couple of teenagers, and straight into my parent’s bedroom, since fucking Cynthia there a few weeks ago, I had started to sleep there myself, so perhaps I should now refer to it as my bedroom. Our remaining clothes were rapidly removed and we began feasting on each other’s bodies. As I had thought, Sally is quite slim with small breasts, and I delighted in sucking her nipples to erection, while she had a firm hold on my penis, and it almost felt like we were in a battle to take the dominant role. I hadn’t realised that, with autumn fast approaching, the house had started to become chilly, so I urged her to get under the duvet, where we continued to maul each other’s bodies passionately.

The battle for dominance continued, and Sally managed to get me onto my back, where I decided to admit defeat for the time being. She slid down my body, kissing my chest, then my stomach as she went, and eventually enveloped my cock in her mouth. I had decided to just lay there and enjoy it as she slurped away at my erect penis. I managed to encourage Sally to turn round slightly so I could slide two fingers into her pussy, which she made clear she enjoyed enormously, the wetness of her pussy was a clear give away, and after a while, she orgasmed noisily.

Eventually, she climbed astride my hips and said lustily “I want you inside me” to which I replied “please help yourself.” She threw the duvet off her back, before raising her hips up, positioned my cock at her entrance and slowly lowering herself on to me. I’m not sure whether to describe it as I fucked her or she fucked me, but Sally was clearly in control. She slid up and down on my cock for a while, then impaled herself fully and ground her clitoris against the base of my cock. This was so enjoyable for me as I was able to watch her orgasm noisily, and I felt I had done my bit my mauling her delicate tits. Pinching her nipples roughly while she was in the middle of an orgasm was so much fun.

Sally seemed to be tiring a little, so I pulled her down to my chest and kissed her deeply, before seamlessly rolling her over onto her back with my cock still inside her. She laughed as she realised I had won the upper hand, then she said “I want you to fuck me …… I want you to cum inside me …… make me cum”. I could go on for pages, of how I fucked her, how she wrapped her legs behind my back, how she orgasmed on my cock, and eventually I ejaculated inside her. I am tempted to say it was the best sex I had ever, but I still had the memory of her mother from 20 years ago strong in my mind.

Eventually, my cock softened and I slipped out of her, although my brain would have liked to carry on fucking her for hours. We must have been tired as we dozed off to sleep, and when I woke at about 5 am, she was snuggled up to my chest. It crossed my mind that I had not licked her pussy yet and, whilst I was enjoying the feeling of her body against me enormously, I had an overwhelming desire to stimulate her orally. I tried to roll her onto her back without waking her, but she groaned as I was doing it and, when I pushed her knees apart, I thought she was going to panic but, when she realised where she was, I felt her relax and draw her knees up. As soon as I started to lick her clit, I could taste my sperm leaking out of her, mixed with her own vaginal juices, which tasted really sweet. The bit I enjoy most about stimulating a lady orally is the strength of her orgasm, the more she shouts her pleasure really does it for me.

After I had allowed Sally to calm down, she grabbed hold of my head so she could look me straight in the face and say “I want you to fuck me again …… from behind this time”. Doggy style is easily my favourite position, as it enables me to get greater penetration and it leaves my hands free to maul the lady’s tits and stimulate her clitoris. In the event, Sally wanted to stimulate her own clit, which she did quite vigorously as her passion rose, leaving me to maul her lovely tits. Pinching her nipples roughly was fun as it made her gasp with pleasure and she was also quite vocal in demanding that I fuck her harder as I did it. Needless to say, spraying my sperm inside her made me feel ‘all-powerful’ for the second time that night.

We slept again until after 9 o’clock, I offered her breakfast but she said she would have to sneak out to avoid being seen by her mother. As she dressed, with me lying in bed admiring her beautiful body, Sally said “well, you’ve fucked both mother and daughter now …… but I won’t ask you for any comparisons”. I was lost for words, thinking of something to say, and she added “you should never under-estimate the relationship between mother and daughter …… see you again soon, I hope”. With that, she was gone, and I was left to ponder my future.