My Fuck Buddy 1999-2010

This is a true story about a friend of mine who also became my fuck buddy for over a decade. I have changed her name so will call her Helen here. I have known her since the early 1990s through work and she is 10 years older than me. For the first 7 years she never talked about a partner (just an ex) but she talked a lot about her daughter. In 1999 I had come out of a relationship and had started swinging again.

It was late 1999 when her boss retired and I was invited to his leaving drinks. This ended up turning into a meal and a late night. Helen had had a bit too much to drink so I suggested she come home by tube with me and stay in my spare room (I was only 5 stops away whilst she lived a tube ride and a long train ride away). She agreed and we were soon at my home. I made us some hot drinks and we sat talking. She asked me why my ex and I had split and after explaining to her I asked her about whether she had a man in her life.

She laughed and said that would be telling. I suggested she should tell me. Helen said that I would probably be shocked so better not ruin what I thought about her. I then told her about my swinging past and that I was again swinging after my split. She didn’t believe me so I gave her more details. I then said it was her turn. She said that she had been hurt when her ex walked out on her leaving her with a young daughter. She had decided at that point she didn’t want a permanent guy in her life and wanted a safe and stable home for her daughter. Her ex took his daughter every other weekend and some week nights that gave her time for herself. She then said that she had set up a small group of fuck buddies. All knew she was only after a sex life and any benefits that came with that. She said that she normally had 5 or 6 guys she could call on but it wasn’t always for sex. For example there was a guy in his 70s (in 1999 she was 45) that would wine and dine her and then they would go back to his house. He would spend the night just fingering and licking her pussy, and giving her loads of orgasms, but he couldn’t get hard so she would make him cum once (often swallowing his cum). She then said there was a guy in his 20s she met just for sex and he could fuck her for hours.

I told Helen that she had opened my eyes and hadn’t realised what a sexpot she was. I went to my bedroom and Helen went to the spare room. I was in the bathroom doing my teeth 5 minutes later, when she knocked on the door and asked if I had an used tooth brush. I opened the door and she was there totally naked. I invited her into the bathroom and got out an unopened toothbrush and gave it to her, and jokingly said I didn’t want it back. We brushed out teeth side by side and I left her in the bathroom. I went to my room, stripped and soon had an erection thinking about Helen stood there naked in the bathroom. I was about to start to play with it when Helen walked in looked at my cock and said that was the effect she had been hoping for. She told me to move along in the bed and she got in beside me. Our naked bodies touched as she leant forward to kiss me and with little foreplay she was soon on top of me and guiding my bare cock into her pussy. She rode me for ages and she would lean back to give my hands access to her clit every so often so I fingered her to orgasm a few times, with my cock being squeezed by her contractions. Eventually her actions got faster and when I said I was about to cum she didn’t get off and instead made me cum inside her … she said she could feel my cum spurting out. She laid on top for a while and then rolled off and we fell asleep cuddling. I was woken next morning by the sound of a shower, When it had finished I went into bathroom and we chatted as she dried off. She apologised for what had happened as she tried to keep friendship and her sex life separate. She didn’t regret that we had fucked but would regret it if changed things between us. I told her I wasn’t ready for another relationship just yet but did really enjoy fucking her. I said nothing would change. She left the bathroom and went to the spare room. I had a wee and returned to my room. In less than 30 seconds she entered my room and said ‘oh fuck it’. She knelt in front of me and gave me an amazing blow job. She didn’t stop sucking until she had swallowed all of my cum. She then laid on the bed and said ‘now my turn’. She opened her legs and I planted my face between her legs and started to lick her pussy. Her clit was easy to fine and giving her an orgasm was so much easier than it had been with my recent ex. After orgasming a couple of times I said I wanted to fuck her. I asked if I should wear a condom and she said that it was rather pointless today as we had fucked last night without one. I got into the missionary position and fucked her and this time as I came inside her she wrapped her legs around me and pulled me in as tight as she could.

As I pulled out I got a great view of my cum dribbling out. Helen went off and had another shower and got dressed while I made breakfast. I walked her to the tube station and we kissed goodbye. That night she phoned me and we had a long chat. She said she wanted to continue fucking me but it would generally be on her timetable and I agreed. We didn’t meet over the next few weeks but chatted a lot mainly about the ground rules. One of these was that I wasn’t to ask about the other guys and she would share any information about them when she wanted to, she said that some knew about the other guys, some thought they were the only guy she was fucking. Another important rule was that she only fucked guys singular she didn’t want the lives crossing over as it could become complicated … therefore she only met one guy at a time.

A few weeks after our first fuck she invited me over to stay the night. It was a Friday and her daughter was her father’s for the weekend. When I got there it was a bit odd and we made small talk. She suggested we go out for a meal at a local pub and it surprised me when she said she needed to change that when she came downstairs all she had done was take her bra off. She said it had been cutting into her but I could now see her well defined nipples through her blouse. She then said that she did like the attention she got when out braless. Over dinner we talked about work, family etc …. Things friends talk about. It was hard concentrating with her nipples so on view through her top.

However when we got back home her sexual animal came out. I went into the lounge whilst she went to make hot drinks. She brought them in but by this time she had stripped naked. She Sat opposite me and said that I needed to know what she was really like. She then said that since our first fuck she had met four of her other fuck buddies. Most had been daytime meets at their place and then she described in great detail what she had gotten up to with them. She would re-enact some things like rubbing her clit, or squeezing her nipples.

She described their cocks, their cum (amounts and taste) and what each one does for her needs (whether social or sexual). She said she always had at least on guy in his 20s in her circle just for the wold animal sex, their recovery time and jokingly she said helping them to fulfil their fantasies of fucking a woman old enough to be there mother. Other guys were there for long slow fucks which had passion. She wasn’t sure what role I would fulfil.

She told me to strip and as she sucked my cock she took breaks to describe what her other guys like being done to their cocks with her tongue. We then went to her bedroom where we fucked several times before falling asleep. We fucked again in the morning before she having a shower and dressing. She made us lunch and then said I had to leave as she had another male guest coming to stay that night. I got home and thought about this sexual agreement and thought it was great. It got better next morning when my phone rang and it was Helen. She whispered into the phone something along the lines ‘thought you might like to know, I am stood in the kitchen naked after just being well and truly fucked and their cum is dribbling down my inner thigh, she laughed and hung up.

Over the next few months we met up once every couple of weeks for a fuck, sometimes staying over night, sometimes not. I still did some swinging and she seemed very interested in the idea but not necessarily wanted to be in a position where she would feel uncomfortable. She agreed to come with me to one of the adult cinema’s in London (this was near the Angel, Islington). I had been a few times before by myself and even though it was mostly guys in there wanking couples did turn up and either fuck with everyone watching or play with other guys there. I warned my friend that some guys might be too pushy. We met at the tube station and she was dressed for possible action. She had a coat on, but underneath she was wearing a skirt (no knickers) and a loose top (no bra). We went for a drink first and then went to the cinema. We walked down the stairs and went into the cinema. It was dark and our eyes adjusted. We then sat in some nearby seats but the cinema was quite empty. A couple of guys were openly wanking and Helen watched them. I put my hand up her top and started to play with her nipples and she started to rub my cock through my trousers. I undid my zip and she got my cock out and stroked it. I then put my hand up her squirt and finger fucked her. Her moans attracted attention and some guys moved closer to see what was happening. I wanted to see how far she would go. I went back to playing with her tits and pulled her top off her. She sat there with her tits on show. Unfortunately the fun was ruined by one idiot. One of the guys who had moved closer, now got on the row in front of us. His cock was very close to Helen’s face. Without asking he grabbed one of her tits and squeezed it hard. She slapped him away and grabbed her top and put it back on. He had made her feel so uncomfortable that we left the cinema. She said she wouldn’t try anything like that again because she was willing to try her limits but the disrespect shown had put her completely off.

I then got a job in the Caribbean and we discussed how this would work. She suggested that we just see what happens. This was 2000 and as soon as I got out to the Caribbean I set up yahoo accounts and we used very slow and poor internet to chat and wank for each other on cam. She then said she could get a break away from her daughter for a week and she came out and stayed with me. It was a very interesting week. I picked her up at the airport and as soon as we got back to my house we stripped and fucked. I then took her out that evening and we had a great dinner and when we got back we fucked several more times. Next morning we fucked before I went to work and she went and explored the island. Over the week, if she was home when I got home she was sunbathing topless or naked and even if lunchtime we would fuck, often outside. She started something new as well.

One morning I was lying on the bed naked, eyes shut. She then said smile, and I looked at her and she was stood with a camera and took a photo of me. This was on film (no digital cameras then) and she said she wanted a reminder of my cock. I waited for her to get into the shower and I surprised her and took a photo of her in the shower, and then that night on the bed. I also found a polaroid camera at work and that evening took some photos of my cock in her pussy and my cum on her belly.

When she got back to England we chatted on camera and wanked for each other at least once a week. I then got a digital camera and started to send her naked pics. Helen then got a digital camera and we regularly exchanged nude photos. When I returned to London on holiday I stayed at Helen’s house for a few days when her daughter was away. The first day there Helen allowed me to do a mini photoshoot with her, including her naked and sucking my cock. We spent a lot of time in bed but one of the sexiest things happened during this visit. She had arranged a lunch time meet with one of her other guys. We had fucked in the morning and she then washed, dressed and left for her lunch date.

She got back at around 5pm and told me to go straight to the bedroom. I was ordered to strip off and lie on the bed. She stripped off but left her knickers on. She stood at the end of the bed and told me what she and the guy had done and how they had fucked. She then said that just a few minutes after he had cum inside her she had dressed without washing and it had taken her 15 minutes to drive home. Therefore less than 30 minutes earlier she had had another guy’s cock emptying his balls into her. She removed her knickers and made me look at them and there was clearly cum on them and she then held them close to my nose and told me to sniff them. She then got onto the bed, got into the 69 position and lowered her pussy onto my face. She stroked my cock and told me to lick her pussy, saying that she had told the other guy that she would be getting me to lick her clean. I licked her clean and then then she mounted my cock. She didn’t normally talk dirty during a fuck but that day she was getting off on the idea she had fucked two guys in under an hour. I was soon emptying my balls into her as well.

I got back with my ex but Helen didn’t mind the occasional fuck when I came back to UK on holiday. She loved the idea for me to go back to my ex after fucking her. We still swapped photos and the occasional photoshoot. I became single in 2005 again and Helen came out to visit me in the Caribbean during my last year there in 2006. I had moved house and this one came with a weekly gardener. My ex had lived with me in the Caribbean for 4 years. The last year we had lived in this house and I realised that the gardener came early in the morning (before sunrise) so he could work his 4 hours or so before it got too hot and he would walk past the bedroom and look in. The bedrooms only limited curtains and I caught him looking through the window as my ex slept naked. I managed on a few occasions to wake my ex and without her knowledge fuck her whilst the gardener secretly watched on. She never found out.

When Helen came to stay in the new house I warned her about the gardener and rather than be shocked she said she was going to tease him. Before his day though we had a few days and had great sex. Even though I had captured a few 15-30 second videos of her on my camera she had never allowed me to make proper films. I had just got a new video camera and when she arrived asked if she would make a porn movie with me. She said no, but a few days in I got home from work and found her sunbathing naked outside. We would normally fuck but when she saw me she said she was likely to regret it but I could go and set up the video camera in the bedroom. We made a great video of her riding my cock.

A day later she said that she wanted us to fuck in front of the gardener. He was due next morning so we hatched a plot. It was for his thrill as well as ours. We woke 30 minutes before he was due and laid on the bed. We heard him arrive and Helen put on the bedroom light as it was still dark outside so he would get a better view. I suggested she go into the bathroom for a few minutes so if he did get to the window he could watch her walk into the room. I laid on the bed and saw some movement outside the window Just as Helen walked back into the room. She came back onto the bed and we kissed passionately. She then laid on the bed and played with her nipples and then held her pussy lips open (she was facing the window so he had a good view of her pussy). I licked her to orgasm which seemed very intense, probably with the added thrill of having an audience. We had decided that she would ride my cock as it would give the best view to the ‘audience’. She mounted me and slowly rode me and after a while she sped up and we both orgasmed as I came inside her. We cuddle for a while before she rolled off me and laid next to me with her legs wide open, giving him a good view. We stayed in the room and a few hours later I dressed and went to work.

When I got home she told me how she had spent the whole day naked around the house and hadn’t washed after this morning’s fuck. The gardener had seen her a lot and she even talked to him naked, offering a glass of water to him. She said that as early as she could, when he was away from the house she had walked round the house and had found dry cum on the floor below the bedroom window so assumed he had enjoyed himself. During the rest of the stay we made a couple of more films.

I returned to the Uk in 2007 and until I met my now wife in 2010 we regularly fucked, and she would tell me about her other guys as we fucked. She is now in her late 60s and even though we haven’t fucked for over a decade she still delights in telling me about her men. It does surprise me that in all these years she has still not had a threesome or moresome.