Developing Jason

by Allan

Copyright© 2019 by Allan

Erotica Sex Story: A young man who needs a help along the way with his confidence in bedding the opposite sex.

Caution: This Erotica Sex Story contains strong sexual content, including Ma/Fa   Fa/Fa   Consensual   BiSexual   Fiction   Cream Pie   Exhibitionism   Masturbation   Voyeurism   .

I am Fiona, age 37, career woman and single, I was married to John but that ended 18 months ago, reasonably amicably. I could not conceive due to a serious illness when I was 15 meaning being childless for life. I had come to terms with this situation long ago and am content with my lot. I married John full in the knowledge that we would be childless, initially he was happy with this but as time wore on it became a real issue. John found a younger woman who was keen to settle down and have kids, he admitted the affair and we split and divorced quickly. I sometimes see them, John, Clare and their young son.

I am happy being single, I have had attention from guys but I can’t summon up the energy to start up a new relationship and all that that entails. I have used them, I admit, although I am not plumbed for conception I have, and always have had, a very great interest in sex in all ways. Maybe the fact that I cannot conceive makes me more relaxed and hungry for sexual activity, I don’t know nor do I really care. All I know is that I take a very healthy interest in my body and the bodies of others, both male and, at times, female.

I do see a female friend, Sara, for sex, who is married, and we meet about once a month at my place for fun. Her husband is aware of her needs and is content that she has an outlet for her lust with me. The last thing I want to do is split up their happy relationship so I keep in the shadows mainly and restrict our time together to when she can get away, for an afternoon or even overnight.

Although 37 I am still an attractive woman, tall at 5-10, slim, brunette, size 12ish and 34d cup. Being tall I have long legs slim through exercise and sport. I enjoy attention from men, I dress to attract them and I am not averse to the odd flash of stocking top, or breast cleavage. It’s all good fun and I am happy to take the lead if there is someone I want to bed. I don’t really have a type of man that I prefer more than most, I like them slim, fit, I love and adore a hairy chest and of course I like them to know what they are doing. A big penis is ok but not the be all and end all for me, I have had many a fantastic orgasm with a guy who sports an average sized penis. It’s all about his technique and skill and my ability to make him happy and arouse him that matters.

My interest in sex stems from the time after my surgery, once I had recovered I started to experiment both on my own and with others of my age, although I had a fling when I was 18 with a guy who was, at the time, 38, now he was a fantastic lover who taught me much about my body as well as his.

So that is really who I am and where I am at now, content with my independent life and happy in the knowledge that I am sensitive to others feelings and keen to make friends as I go along.

During the holidays I was invited to my cousin Jim’s for a weekend with him and his wife Julie, we were always quite close as they knew of my background and the reasons for my failed marriage. I was always comfortable in their company and they were particularly supportive during the divorce. They appeared to be devoted to each other and have two children, Jason 19 and Annie, 17 years of age. Jim was that bit older than me and he and Julie had been married for some 21 years or so. I really like Jim he was a rock for me when I was going through the treatment those many years ago now.

Julie was great to have as a friend, she was a bit scattered brained but easy to get alone with and I was more than happy to confide in her about what was going on in my life as she was with me. She told me things about Jim that surprised me, about their relationship and their varied sex life. I never had eyes for a Jim, we are related but not closely so it would have been ok, Julie although was another thing completely. I have been having sex with Julie for many years, Jim knew about this and was more than happy for the arrangement to continue so long as he was able to watch. A similar situation as the one I have with Sara really.

On the Friday night after dinner we retired to the family room, both Jason and Annie were out and not expected back until the following morning. I was really pleased to see them when I arrived both of them developing into fine your people. A college sporting event meant they had to stay over for the night and I would see them again on the Sunday.

Wine with dinner and after left us in a relaxed and playful mood, Julie asking about my love life, “well Fiona, any particular man in your life at the present, have you been seeing anyone?” I replied “what you mean Julie is have I been fucking any one really special, the answer is nobody special but, yes, I have been fucking a few of late.” We all had a good laugh at that, “how about you two still getting plenty of time together for fun and games.?” Jim said, “for sure you know us always trying out new things and perfecting the old ones, anyway it’s always great when you visit Fiona as you know we all get to have a little fun.”

At that Julie sat closer to me and put her hand on my knee, I was wearing a mid thigh skirt matching blouse and black stockings. Her hand moved up my thigh under my skirt and to my stocking top. I turned to Julie and kissed her full on the lips. Julie’s blonde hair fell down, I cupped her breast in one hand as I fell her inner thigh with the other. Our tongues entwined as I opened my long legs so that Julie could have access. We started to strip each other, shirts off breasts touching as we stared into each other’s eyes, she unfastened my bra first, allowing my tits to fall out before her, she tweaked my nipples causing some exquisite pain. I returned the compliment and released her breasts from her bra, her tits being slightly smaller than mine. Her areola’s bigger and darker than mine, always a big turn on for me.

We now kissed deeply feeling each other’s breasts, nipples and bare skin. I unhooked my skirt which fell away leaving me in my black hold up stocking and black panties. Julie slipped off her slacks leaving her in just a small pair of red panties. While all of this was going on Jim was really enjoying the spectacle, his shirt was open, he had removed him trousers and underwear and he was stroking his erect cock. We both glanced over at him grinning to each other as he masturbated.

I usually take the lead with Julie, I laid her down n the floor removed her panties and admired her bare hairless pussy. I spread her legs and went down on her finding and licking her clit, I inserted a finger in her pussy as I worked on her beautiful pussy feeling her hard little bud. As I fucked her I alternated between fingering her cunt to massaging her anus enjoying her pleasure so much. She came quite fast as she was really excited, her pussy puffed up, soaking wet and red, she squeezed her lovely thighs against my head as she climaxed, saying, “ fuck me Fiona, I love you fucking my hot wet cunt.”

I came up to her and we kissed deeply, I started to grind my well trimmed pussy against her bare wet cunt. Our tits meshed against each other’s, nipples hard to the touch. We fingered each other and kissed and fondled as Jim stroked his cock watching us with great interest. The feel of Julie’s skin against my nylon clad legs was fantastic, “ I can’t get enough of your hot body Julie, I just love fucking you”, I moaned, as I came, hard waves of passion wracking my body as I came, Julie following after me by seconds. We turned just in time to see Jim ejaculate, several spurts of white spunk arcing from his hard cock.

We cleaned up and sat and chatted wearing only robes, I still had my stockings on but bare underneath as were Jim and Julie. I could see Jim getting hard again as his cock tented his gown, Julie did not miss this either and uncovered his hardening member, opening his robe and going on all fours as she took his cock in her mouth. She peeled back his foreskin to reveal his glistening knob before she expertly sucked him to full erection. She gave as much attention to his balls as she gently squeezed them. I was mesmerised at the sight so I removed Julie’s robe exposing her perfectly rounded bum, her anus and pussy all on show. I could not resist her so I kissed her bum cheeks, rubbed her anus and slowly massaged her cunt from behind.

Jim being that bit older took some time and was really enjoying the blow job he was getting from Julie, Julie in turn was moaning with pleasure at the attention I was giving her pussy. I was rubbing my tits on her back as well as attending to her pussy and anus, she was near to orgasm. At that Jim arched his back and came in Julie’s mouth, she lapped up his spunk eagerly, just then she orgasmed at my touch her bare cunt soaking wet with her juices and per anus puckered from all the massaging it was getting. I was in awe of this fun, it was so fucking erotic I sat back and masturbated to a quick orgasm as my friends watched, tired an sated. A night to remember for sure, and one to be repeated at an early date. All to bed now to sleep and dream about what had taken place.

Up by 08.30 showered and ready for the day, both Jim and Julie followed soon after for breakfast. Wry smiles as we recounted the previous evening, Julie disclosing, “Jim was so turned on he fucked me first thing this morning, a rare treat”, she joked. We ate a leisurely breakfast before clearing up. Jim had to go into town so Julie and I chatted and got up to date on things in general. Both Jason and Annie were due back home around one in the afternoon so we prepared a late lunch for them and awaited their arrival. It had only been about two months since I had seen them but I was eager to see them again as I was very fond of them both.

As we worked I asked Julie how the kids were doing, she said they are fine, school and college going really well. Annie had a steady boyfriend who seemed to be really good for her, she was sexually active, explained Julie, she told her mother absolutely everything. Jason had had a few girl friends but nothing that lasted very long, Julie said she was a bit concerned that Jason was a bit shy and reserved around girls and women. She said that he was not gay, not that that mattered one little bit, just a bit slow when it came to the opposite sex, and maybe sex in general. Both kids were attractive, Annie a cut down version of Julie, blonde, lovely legs and small breasted. Jason tall fit, broad chested, a real good looking guy.

“Jason really needs a woman to take him in hand, someone who is experienced and would give him the confidence he lacks right now” said Julie. I said,”it’s a real shame for him as he is such a sweet guy, most girls would love to be his girl friend.” Julie was about to say something more when the two youngsters arrived home. Hugs and then lots of chat catching up followed over lunch, they certainly were a joy to have around. Jim returned mid afternoon so we all sat around chatting before showering and changing as I had booked dinner at a nearby restaurant, my treat in return for their hospitality.

I wore a red print dress, black stockings, Julie had on a grey skirt and matching shirt. Annie a mini dress showing off her young curves and shapely legs. The men were in shirts and slacks, both very handsome. The meal was a tremendous success, we sat over coffee for a long while before settling the bill and returning home, it was a fantastic evening. During the evening I seemed to notice Jason’s eyes lingering on me more than usual, of course I was flattered and flirted with him just a little. I was sure that he got a flash of my stocking top as I crossed my legs when he was returning from the men’s room.

We returned home the two youngsters said goodnight and went off to their social media stuff no doubt, telling friends all that was happening in their lives.

Jim, Julie and I sat sipping a late drink chatting mainly about the youngsters, Jim concurred with Julie in that he thought Jason was lacking some confidence with the opposite sex, and whereas he is an attractive and good looking guy it seems that he was not completely at ease with girls. Julie reiterated her view that he needed an experienced woman to help him with his confidence and just be there for him. Jim shocked me to the core with his next comment, “maybe you could help him out Fiona, after all he thinks a lot of you and loves you in his way, what about it.” I said I am not really sure how I can help out Jim, I am more than happy to talk to him and see if I can advise him but I am not that sure that is what is needed, what do you think Julie,” I asked. Julie agreed with me, “ what he really needs is an intimate experience with an older wiser woman, let’s not mince words here, what he needs is a really good fucking with someone who can show him what a woman needs, so how about it Fiona.”

I was almost speechless, we explored the notion about me taking their son in hand, so to speak and they were of the same mind that if he had to be with someone experienced and wiser it would be so much better with me than some hooker or escort who was only fucking him for the money. I said I would sleep on it and give their suggestion every consideration. As the young people were in the house we would not indulge in any sexual activity, unfortunately, so we kissed and hugged goodnight and went to bed.

I tossed and turned all night thinking over the proposal put to me about Jason, he is a very attractive young man, and having him between my thighs was certainly a very erotic thought, one I could not put out of my mind. Showering in the morning I was still unsure what to do, I thought I would clear my mind by masturbating in the shower, a thing I regularly do to start the day off. As I was fingering myself I could not get the image of Jason out of my mind, the thought of his cock inside me sent shivers through my body resulting in a fantastic climax and orgasm. I suppose the early morning pleasure made my mind up for me, I would accept the offer in the manner it was intended, in that I would be helping the young man and in the process have lots of fun at the same time. I was an assertive and confident decision maker, so that was it I would somehow engineer a situation where I was alone and had all the time in the world for Jason.

Jim and Julie were eager to hear my thoughts about their proposal to me for Jason. I wanted to keep them guessing for now, and at that Annie appeared for breakfast closely followed by Jason so no time for chat.

Over breakfast I asked Jason, “So the college paper you were telling me about have you a copy so that I can go over it for you.” “Actually I would rather you went through it with me instead of going over it by e mail, the only problem is I don’t have a copy here and I can’t remotely access the file on the college computer as it is restricted for security.” “That’s a pity maybe you can get the copy and bring it over one day next week, I am only 10 miles or so from college and I will be working from home for most of the week, how about Wednesday afternoon, would that suit.” “If that’s ok Fiona, that would be brilliant as I value your opinion so very much.” “That’s settled then, Wednesday afternoon is agreed, I will look forward to it.”

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