Discovering Sean, Discovering Myself

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Hi – this is my story – some parts are real – the actual sex parts are not – just a fantasy that I want to turn into reality. I hope you enjoy reading it. Under 18 – go away.


I had just turned fifty and after a rough session with my doctor I knew I needed to turn my life around. At 5′ 6″ I weighed in at 215 pounds, my blood pressure was through the roof and so was my cholesterol. My wife was nagging me; my kids were nagging me; and now so was my doctor.

Determined to finally do something and highly resistant to the thought of taking pills to deal with my health problems I got off my ass and started exercising for the first time in 20 years. I live in the Santa Monica Mountains in Ventura County California, surrounded by beautiful rolling hills, most of which are protected parkland. So I working out and bought a mountain bike.

I discovered our local community center gym. This facility hosted numerous leagues for basketball, volleyball, badminton and various martial arts classes. It also had two indoor racquetball courts. This was a sport I once played well, so I started playing again with a vengeance and the rest of my spare time was spent on the mountain bike. My wife was thrilled that I was finally beginning to lose weight as she wanted me around for another 30 years and so did not begrudge the time spent away from her. As my kids were both in college and I worked out of my house, I had plenty of time to exercise and spent almost two hours a day working out.

Six months later I had dropped over 40 plus pounds, and more important (to me) I had a flat stomach and a 30″ waist. Something that I had not had since I was in my early 30’s.

Around that time a new guy showed up for our Friday night challenge court racquetball games. The format was simple – two guys played, the winner kept the court and the next guy on the list took him on. Guys of all levels played and the fun was in matching your skills against a large variety of other players.

It was a loose knit group of players, some came every Friday, others once a month or so, but I had never seen Sean before tonight. I am not sure why I even paid that much attention to him, but I did. Perhaps it was because not only was he new, but he also seemed a bit intimidated and I knew that feeling, remembering my first time on a Friday night.

I introduced myself to him, and then, in turn introduced him to the other players that were there that night.

Sean explained that he had just relocated to Ventura County from Florida. He was a biochemist working for Amgen, a major employer out here and was trying to meet people, as he really knew no one in the area.

There was something about him that felt odd, but I could not put my finger on it. He was very similar in build to me, slender, about 5′ 8″ with long blond hair, bound up in a ponytail. He had blue eyes and I noticed that his lips were very full, which shocked me, as I tended to not really notice what another guy looked like.

I considered myself straight and while I had been through periods in my life when I fantasized about sex with another man, I worked hard to repress those fantasies. Now, remarried after 10 years of being divorced, the last thing in the world I was going to allow myself to do was to fantasize about male-to-male sex.

But something about Sean kept bugging me and I did not know what it was. I would see him on Friday nights at the racquetball court, and after a month or so I asked him if he ever wanted to play one on one.

I explained my flexible schedule to him and we agreed to start playing on Wednesday during the lunch hour. After a few weeks of play I found I really looked forward to seeing Sean and also came to feel that he was gay. I based this assumption in part, after repeatedly trying to engage him in conversation about the dating scene in our little valley. He would evade the subject or brush me off. I also started noticing how he would watch the other guys on Friday nights, not only observing the action on the court but also scoping out the guys sitting, waiting to play.

I found myself intrigued by this fact, and almost against my will I started gently flirting with him; nothing obvious, just a slight pat on the butt after we finished playing our weekly lunch game, or a light hug when seeing him before we played.

He, in turned started reciprocating the touching, though nothing was ever verbalized. I found myself looking at his full lips, wondering what it would be like to kiss them, and to run my tongue across them.

In addition to his blonde hair Sean had incredible eyelashes, and with the right hairstyle and makeup I could imagine him as a beautiful woman. Between the flirting and my imagination I soon found that Sean was the subject of more than one jerk-off session.

I would find my cock getting hard at the most inopportune times on a Friday night while watching him play. Looking at his beautiful bubble butt, covered in tight, girlish shorts, casino siteleri his long legs, covered in the slightest downy soft blonde hairs rekindled my long forgotten desires for sex with another man.

I did not know where or even how to act on my desires, or even if Sean were truly gay, much less if would ever have an interest in someone like me, almost old enough to be his father.

I finally decided to “up the ante” as it were and see what happened by changing my after game routine on Wednesdays. Working out of my house, I would finish play and go home to shower and change. Sean, heading back to work would always change at the gym.

One Wednesday I told Sean that I would be showering at the gym as I had to head out to a meeting in Camarillo, so I did not have time to double back to my house. He seemed a bit taken aback by this but did not say anything so we played our usual hour of intense racquetball.

As we headed toward the locker room I could feel that there was the beginning of an unusual sort of tension between us. Not bad, but almost, dare I say it, sexual in nature.

During the middle of the day the gym is virtually deserted. There is a pickup basketball game that takes place upstairs but Sean and I were usually the only players on the racquetball courts so the locker room is always empty.

We both undressed and headed for the showers. I noticed that Sean yanked his shorts and underwear off in one quick pull, though I thought I detected a hint of pink, in contrast to his bright red shorts. Shrugging it off, I followed him to the shower, again admiring his butt and hoping that it did not trigger a hard-on.

I could not believe that I was actually going to be naked with that beautiful young man that I been fantasizing about. I was scared to look at him as I thought it might trigger an embarrassing hard-on, when I heard him say, “wow, you are really hot, you weren’t kidding about the working out thing.” I had explained to Sean about my struggle to loose wait and get that stomach back to where it not been for 30 years.

I thanked him for the compliment and told him that he was going to make me blush if he kept it up. I was shocked at what came next when he uttered the old Mae West line – if I told you that you had a nice body would you hold it against me?

I looked at him for a couple of seconds, and I could see that he was scared that he crossed a line he should not have crossed. I smiled and thanked him again for the compliment and told him that in another time and place I might just do exactly that.

I felt free now to stare at him and did so openly as he looked at me. Our flirtation was now bordering on the erotic as it took on the beginnings of solo foreplay. I slowly washed myself, almost caressing my tits and belly. I made a point of turning and facing the wall while I washed my ass, giving him a good view as I made sure that I cleaned all around and in my hole.

This in turn caused my cock to waken slightly, which brought an equal reaction from Sean. I am totally average in the cock department. Small when soft, a basic six inches hard. Sean however was more than adequate. He had one of those cocks that as I was to learn later did not get too much bigger when he was hard. Soft, it was quite impressive and I took advantage of our flirting to stare at the first live male cock that I had seen since high school.

As he had been so bold to compliment me I told him that I thought he had quite the specimen. He blushed and thanked me and I saw his cock twitch again and rise to a semi hard state.

We both had finished washing by this time, finishing off by engaging in some slow soaping of our half hard cocks, so it was time to get out.

We started to dry off and then dress and I noticed that Sean was taking his time, almost as if he did not wish to dress in front of me. I stopped and asked him what was wrong, why he was still naked, as I knew he was officially late for work as a result of our lollygagging in the shower.

He blushed again and mumbled something so I repeated the question. He finally told me, while staring down at the floor, that he was embarrassed to get dressed in front of me. I asked him why and he replied that he had inadvertently grabbed a pair of his girlfriend’s panties by mistake and did not want me to see him in them.

By now, I knew that Sean did not have a girlfriend, but I did not want confront him so I simply said it was ok by me; that I personally enjoyed slipping on my wife’s panties now and then and to not to be embarrassed by it.

Sean then slipped on a pair of hip hugger yellow panties with a lace edging. It was obvious to both of us that he could not have “accidentally” slipped those into his bag, but that fact was left unsaid. Seeing him like that brought back all of my old fantasies of being with another guy, dressed up in soft, silky under-things, and my cock sprang up hard as a rock in seconds. I quickly slipped on my pants and a shirt slot oyna so as to hide the evidence as it were.

I gave Sean a hug and slipped out of the locker room, my mind reeling with the thoughts about all that had transpired in the last several minutes.

I was now about 100% sure that not only was Sean into lingerie but he was gay, and that I turned him on. What to do about it? Did I really want to pursue him, give in to my deeply buried urges to finally have sex with another guy? Looking at his cock in the shower, I could imagine getting down on my knees, kissing the head lightly, slowly licking the long shaft as it hardened in my hands.

I could see myself licking his large balls, sucking each one gently into my mouth and then sliding up his silky smooth body until my lips met his in a passionate kiss. I drove him with a cock leaking pre-cum all over my dress slacks (the meeting was nothing more than a made up cover story). I ran into the house and ripped my clothes off and stood in our upstairs hallway, naked, saying his name and imaging us being together in bed. I came hard, all over our hardwood floors and quickly wiped it up as I struggled with my feelings of lust for Sean as weighed against my love for my wife.

The next day, after a night filled with erotic dreams I returned to a site that I had long since vowed to never visit. I was a site that made panties and other sexy undergarments for men and over the years while I was divorced I had bought many a sexy pair from them, abandoning them all when I got married.

I ordered my personal favorite – the Dorothy short. It was a pink and white gingham, trimmed in lace, cut in the ever so girly “boy short” style. I paid the extra cost for Fed-Ex as I wanted to push the game along at our next Wednesday session.

Wednesday could not come soon enough and I finally found myself back on the court with Sean. This week he had come wearing a pair of pale blue French cut shorts with a midriff top showing his belly button. He also appeared to be wearing just a hint of lipstick, perhaps applied in the car outside for my benefit?

I gave him a generous hello hug and copped a quick feel of his ass cheeks, as he did the same to me. We played our usual game, though not with anywhere near the same intensity. We both kept “clock watching” wanting to get to the showers and see what would happen next.

As we headed to the showers Sean again undressed quickly, not letting me see his underwear. Once wet we both repeated the silent flirtation of the prior week, soaping our asses, our cocks. I held my ass open and ran my finger around the hole, making sure it was squeaky clean. Sean, in turn did the same.

After showering I was quick to pull out my Dorothy boy shorts and slipped them on, with my cock hardening as I pulled them up. Sean sat and watched me and commented on how well they fitted me and how hot I looked while wearing them. He in turn pulled on a pair of panties similar to what he wore the prior week and then we both completed dressing and left the locker room with prominent hard-ons hidden beneath our dress slacks and shirts.

This pattern continued for several weeks, the flirting, the furtive touches, and the mutual dressing up after our shower. I had accumulated several pairs of panties by now, along with some substantial Fed-Ex charges but was no further along in seducing, or being seduced by the man of my fantasies. We did talk openly about our mutual love for wearing panties and I confessed that I also loved to wear stockings, camisoles and other girly things. Sean agreed with me that that dressing up was fun and admitted that he like to do so also.

I was feeling frustrated and not sure of where to go with my desires when my wife announced that she was going to go visit her parents in a couple of weeks. They live several hours away and my wife usually makes the journey herself. While I like her family, I like them in small doses while she wants to make a weekend out of it. So we compromise with her going to see them once a month, and I go with her every other month.

I was determined to take advantage of her absence and decided that easiest approach was to put Sean into a position where I could fulfill his first request made so many weeks ago, to have me hold my body against his.

I invited Sean to go mountain biking with me, using my old bike, and telling him that my wife was going to be out of town, I suggested that we have a guy’s night together after the ride. He jumped on the idea, as did his cock, which sprang to life as I made the suggestion.

Finally the weekend arrived and I picked Sean up and headed out to one of my favorite “newbie” rides. It was a sixteen mile ride, but almost flat with a combination of paved and dirt roads, just one steep one mile hill called black widow which was downhill going out and a long walk up for most beginners coming back. I felt that it would give Sean a good exposure to mountain biking and most importantly help him canlı casino siteleri work up one heck of a sweat as he walked his bike up the hill on the way back.

The ride was terrific, the path goes through the Santa Monica Mountains from the Conejo Valley to Point Mugu on the coast. I brought a backpack and we ate a picnic lunch at the beach, flirting, holding hands, and talking about work, life, my kids and just stilly stuff.

I felt emboldened by the fact that I was in public with another guy, allowing my emotions and feelings to be shown. We talked for a couple of hours on the beach and even moved so far as to start giving each other gentle caresses on our cheeks and shoulders,

We finally started our ride back, hitting the bottom of the black widow, I rode to the top and waited for Sean to make his way up the hill, pushing his bike, as almost everyone does the first time they ride it.

He arrived, all hot and sweaty and looking quite tired but also quite cute, his blonde hair disheveled from wearing his helmet. We loaded the bikes back onto the rack, locked it up and headed for his apartment.

Upon arriving we both agreed that the first item on the agenda was a shower. Hot and sweaty as were both were. Sean, at that point popped the question of “saving water by showering with a friend.” I immediately agreed, as I was finally going to be able to shower with my friend in a private and safe setting. We quickly undressed, and I blushed red with embarrassment as I pulled off my biking shorts to reveal my cock, already half erect in anticipation of what was to come. Sean just smiled and slid his shorts down, revealing his beautiful member.

I noticed that he had shaved and it made his cock look even larger. I remarked on how good he looked shaved and he told me that it was not only comfortable for him, but also a lot more fun to lick that way. I blushed again and said that I would have to give it a try. He smiled again and asked what did I want to try” shaving or licking?” and then told me that he would be glad to show me the ropes as it were on how to get the best shave.

By now we were both almost totally hard and we hopped into the shower. It was obvious where this was going. My heart was beating like a trip hammer as I climbed in with Sean.

I was hard, hot, horny and scared all at the same time. Would I be able to kiss him, what would it be like to kiss another guy and feel the scratchiness of his beard on my face? I wondered if I could go through with my fantasies of actually going down on a guy and sliding his cock into my mouth, sucking his balls and even rimming him, something I loved to do but an act that my wife considered filthy.

Sean sensed my tension and simply stood in front of me letting me slowly relax and stare openly at his body. As my breathing evened out he asked me if I wanted my back washed. I replied with a yes and he started soaping me up. Slowly, gently, sensually running the soap up and down my back, across my shoulders, down my arms. He would take the bar, rub it on his hand and then apply it directly to my body. I reveled in the feel of his smooth hands as he slowly caressed me and calmed me down.

I was ready now and he knew it. His hands descended lower as he began soaping my ass. I spread my legs slightly to let him know it was ok. As he did so he began to lightly kiss me. Starting on my neck, he moved to licking and nibbling on my ear. This is a total hot button for me and I began to moan quietly. He asked me if I liked what he was doing and I told that I would melt like butter on a hot knife it he kept that up.

He just smiled again and started running his finger across my hole. I could not believe how excited I was and how hard my cock had gotten. I felt like I could come immediately if he touched me. His finger continued its slow movement across my asshole. He moved it up and down, around in circles, away from the hole and then back towards it. I started pushing back at him, silently letting him know what I wanted. I felt him begin to push his finger in and I continued to push back trying to get him to give me what I so desperately wanted.

His finger slid in easily and he was a bit taken aback. He broke the silence by stating, as a fact, that his finger was not the first thing to have penetrated my ass. I had to confess that, he was correct.

While I had never been with a guy, I had indeed fantasized about it for quite a while when I was divorced. During the course of those fantasies I had across the Nifty site and discovered the trove of stories.

One in particular had a real impact on me. It was the story of a man who, in order to prepare for his first fucking by his boyfriend bought a dildo and started fucking himself in the shower with it. The image of that caused me to go buy one.

I bought one that had a suction cup on the back end of it. I would attach it to the shower wall and imagine that I was showering with my lover. In my imagination he would push me to my knees and I would engulf his hard, warm cock in my mouth. I would often suck on it until I came, and then I would rub my warm cum all over it and lick it off, as if were cum from my lovers cock.

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