Written by Tim
26 Jul 2017
My journey - a new direction
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13 minute read
I posted my story on here a while ago about how I lost my virginity to a woman called Sarah who works for the same company as me. Briefly, I am an early-30’s guy who, because of my upbringing as a child, had always had difficulties in establishing relationships with women. Sarah is a married woman, 10 years older than me, and I had ended up fucking her in my flat. If this sounds as though she had seduced me, I can assure you this was not the case, I was more than willing for everything that happened. She told me afterwards she felt guilty about cheating on her husband, so she would not do it again, but we continued to see each other occasionally during lunchtimes at work, I had come to regard her as a good friend, as well as the lady who ‘took my cherry’.
My attempts at ‘self-improvement’ certainly seemed to be working, as I was becoming much more confident at chatting to woman. I became friends with several other women at work, and I even had dates with two of them. I went to the cinema with one of them to see one of the films in the ‘Taken’ series starring Liam Neeson, with a drink at a pub afterwards, and I had a dinner date with the other lady, at a very smart restaurant in town. My life seemed a great deal happier, and Sarah told me she had not heard references to me being called ‘the mouse’ for ages.
I continued to see Sarah at lunchtimes from time to time, it was often in the canteen rather than in the park opposite, as we could talk as friends without anybody reading things into it. I had noticed that Sarah was a bit subdued or distracted for a couple of weeks, so I eventually summed up the courage to comment on it, I asked her if there was anything she wanted to talk about. She assured me she was fine and there was nothing I should worry about.
That evening, Sarah texted me to ask if we could go for a drink at the pub where we had been before on the following evening. We found a quiet corner in the pub to talk and she said that her husband had started talking about having a threesome with another guy again. She said the last time had been a total disaster as she didn’t like the guy he had chosen at all so, out of the blue, she had suggested there was a guy she worked with, who she quite fancied. He had asked if it was wise to ‘play’ with someone she knew, but she had pointed out that the last disaster was with someone he knew. She said she had asked to meet me to sound me out, and she would report back to her husband.
I mulled it over for a minute while we sipped our drinks, I recalled that I had been with another couple before and had managed to perform adequately, I had even had bodily contact with the other guy and not been repulsed by it. Eventually, I said “yes …… OK then”. We smiled to each other, happy that something had been resolved.
To cut a long story short, we arranged a ‘social’ meet – Sarah, her husband Alan, and me – at another country pub a week or so later. I liked Alan, he is a pleasant, sociable guy, he said he is an accountant at a small company. Sarah had already told me that he is the Financial Controller and it is quite a large company, so I was impressed by his modesty. Sarah had said he could be a bit over-bearing at times, but all I saw was a guy who, like many of the men on SH, had a fantasy to see his wife with another man. I saw him as polite and respectful. After chatting for over an hour, quite intimately at times, but without actually addressing the practicalities of a threesome, I suggested we should go away to reflect on our discussion, and talk again soon.
Sarah texted me the following evening to say Alan was “red hot keen”. She said they had made love as soon as they got home yesterday, and he had fucked her like a man possessed. I replied that we should meet again at the pub, but stressed there should be no commitment from either side at this stage. Sarah texted me again later to say that, if I decided to go ahead, they wanted it in the comfort of their home.
We met again on the Friday evening of the following week. Alan shook my hand warmly, and I kissed Sarah gently on the lips. As we parted, I realised we were both smiling and, when I turned to Alan, he was smiling too. I bought a round of drinks, and we found a table in a quiet corner so we could talk. Our conversation danced around the subject for a while, and I realised that, because this was a very new experience for all of us, the best we could do is play it by ear.
As we walked out to the carpark, Alan suggested Sarah travel with me as I was unsure of the route to their house, although I managed to follow Alan without getting lost. On the way there, Sarah told me she had told Alan after our first social meet that it had been her who had ‘popped my cherry’ only a few months ago, and he was quite relaxed about what she had done.
When we arrived at their house, Alan went to the kitchen to open a bottle of wine, while Sarah and I sat down in the lounge. Alan came in with 3 glasses, and we began chatting, I thought slightly nervously. I was not too sure how it would start, but Sarah took the initiative when she stood up and said “I’m going upstairs, perhaps you guys can follow me in say 10 minutes”. With that, she smiled and headed for the door. Alan and I continued to chat and, at one point he said “I’m sure you know that Sarah doesn’t like condoms”. I nodded and replied “yes, she said”. I was conscious we were both clock watching, so it was a relief to both of us when we decided it was time for us to join Sarah.
Alan led the way upstairs and, when we got into the bedroom, Sarah was lying in the middle of the bed with the duvet pulled up to her chin. She folded the top corners of the duvet back inviting us to join her, so we quickly began stripping off, discarding clothes everywhere in our hurry to join her. As I slid in on one side of Sarah, I was delighted to find she was, like me, naked. It wasn’t long before Alan joined us on the other side, and we instantly started to stroke her body, kiss her lips and nibble the delightful nipples of her beautiful breasts. We both wanted to offer her pleasure, so she must have felt quite overwhelmed by the attention we were both giving her, but she seemed to be enjoying every minute of it.
She had grabbed hold of Alan’s head to kiss him passionately, so I slid my hand down over her belly to her pubic mound. When I touched her clitoris with my finger, she gasped and stopped kissing Alan briefly, before resuming the kiss even more passionately. I rubbed my hand over the inside of Sarah’s thigh, and she readily opened her legs to give me access. I began teasing her clit gently, before sliding one finger into her pussy, which had already become quite wet. Alan had taken over at the top, kissing her mouth, mauling her tits and nibbling her nipples. Sarah seemed to be in heaven, with her eyes closed and breathing heavily.
I crawled over between her legs, pushing the duvet off the end of the bed, and pushed her knees wide apart. As I looked down at her neatly trimmed pussy, I noticed her lips were glistening with her juices and, when I looked up into her face, I saw that both Alan and Sarah had stopped what they were doing and were smiling at me. I smiled back, before slowly lowering my mouth to her pussy. I licked her clit, making it protrude so I could suck it, and plunged my tongue deeply into her pussy. I noticed that Alan had shuffled up so Sarah could suck his cock, and she was slurping him noisily.
She was clearly orgasming, as her juices were flowing freely. I stopped briefly to allow her orgasm to subside, before saying “can I fuck you now”, to which she gasped “oh yes please”. I slid my cock into her very wet pussy slowly to start with, but there was virtually no resistance, she seemed to be welcoming me in. I quickly built up a rhythm fucking her, while she continued to suck Alan’s cock between the gasps of her continuing orgasm.
I noticed she was having to twist her upper body to suck Alan’s cock, so I decided to try a different position for her comfort. She started to look a bit disappointed when I slid out of her, but when I pushed her onto her side and positioned myself spooned behind her she realised what I was doing and resumed licking her husband’s cock. I raised her knee and slid my cock back in, this position seemed so comfortable for all of us, and I was able to resume stimulating her clit with my fingers, whilst thrusting into her.
I thought I had managed to control my ardour quite well, but I realised that hearing Sarah in a virtually continuous orgasm, whilst watching her licking and sucking Alan’s cock was becoming too much for me. When I announced that I was cumming, Sarah said “oh god yes …… cum in me …… inside me”. As I started to fire spurts of sperm inside her, she had removed Alan’s cock from her mouth and was wanking him furiously, so it was no surprise when he said “I’m cumming too” and she had to quickly envelope his cock in her mouth again. I think she managed to swallow most of it, but he must have cum as heavily as me as I noticed afterwards some was smeared round her chin.
As we lay together on the bed recovering our breath, Sarah turned to me and said “I’ve promised him sloppy seconds, if he can get it up again, but I want you to stay a bit longer”. I went into the en-suite to clean up a bit and, when I came out, Alan was fucking Sarah doggy style, and she was orgasming again quite loudly. I sat down on the chair to watch, I decided it was so enjoyable to watch this husband and wife enjoying each other.
I noticed Alan was scooping up some of the ‘juice’ that was leaking out around his cock, and was smearing it over Sarah’s anal sphincter. When he gently slid one finger into her arse, Sarah raised her head and said “ooooh” before burying her head in the pillow, gasping and groaning. Alan continued to fuck her pussy, whilst burying his finger full length in her arse, and stretching her further with two fingers, which Sarah was clearly enjoying. Sarah was clearly orgasming continuously, but I didn’t notice Alan cum again.
Eventually, Alan withdrew and they both flopped over onto their sides, spooned together watching me and smiling. I hadn’t realised that I had been stroking my cock, but we all laughed when I hurredly stopped. Sarah beckoned me over, so I joined them on the bed and began kissing her and stroking her delightful nipples. She seemed to have come down from her earlier orgasm, but she clearly wasn’t finished yet, as she pushed me over onto my back and climbed astride me. She sucked my cock briefly to ensure I was fully hard, and then lowered herself onto my very stiff member. She started to grind her clit against the base of my cock, I wanted her to sit upright so I could stimulate her there, but she was determined to take the dominant role this time.
She leaned forward against my body and began kissing me, and gasping as she continued to grind her clit against me. Alan was kneeling behind her, and I realised what was going on when Sarah stopped kissing me to say “oh yes …… fuck my arse”. I felt Alan’s cock enter Sarah’s anal cavity, bit by bit to start with and I could tell by the noises she was making that she really wanted it. Once he had her fully impaled, he began to fuck her …… and I started to fuck her cunt as well.
Fucking Sarah’s cunt while Alan was literally centimetres away inside her fucking her arse was quite a new experience for me, but I have to say it was very pleasant. It was certainly pleasant for Sarah, as she wailed away enjoying her orgasm noisily. Alan was the first to announce his climax this time, and Sarah gasped “oh yes …… oh yessssss”. I had been managing to delay by climax up to that point, but I decided I wanted to ‘join the party’ and, as I felt the sap rise, I announced “I’m cumming too” as I continued to thrust into her. Sarah had been telling the world how much she enjoyed it and, as Alan and I filled her cavities, she buried her face in my neck and bit my shoulder. I suppose I should have found it painful, but I just felt it was worthwhile to see Sarah’s expressions of her pleasure.
As we all returned to earth, Alan climbed off and rolled onto his side of the bed, Sarah allowed my softening cock to slip from her very wet cunt and fell on the bed between us. We lay there panting, with arms round each other for some time, which included Sarah turning to Alan and me, and kissing us both passionately. After a while, I decided it was time for me to go, but I had to get off the bed quietly as Sarah had fallen asleep, she seemed totally exhausted. I picked the duvet up off the floor and placed it over her in the bed, she seemed so serene and happy. I then began gathering up my clothes from the floor, conscious that Alan and I had thrown our clothes everywhere in our haste to join Sarah in the bed.
Shaking hands with Alan in the hall was a very strange experience as he was still naked, we said our farewells and I asked him to thank Sarah for what I had enjoyed enormously. The following afternoon, I received a text from Alan on the Saturday afternoon saying “Hope you enjoyed last night as much as Sarah and I did. We hope this will be repeated soon”. I replied that I had enjoyed it too and doubtless we would do it again when I recovered!
I have continued to see Alan and Sarah every 2 or 3 weeks, and we usually include some sort of social preamble such as a restaurant meal, or a trip to the cinema/ theatre, which makes the whole evening, and sometimes all night, a very pleasant time for all of us. I feel that I have cleared my head of the sexual hang-ups of my childhood, and I can now really start to progress my life, both professionally and personally. I have made lots of new friends, both men and women, and I have even joined a gym to keep myself in shape.
But the most enjoyable part of my life is assisting Alan in giving Sarah a good seeing to every few weeks!