A few years ago I answered an In Search Of ad that was written by a local married couple in their 40s who were seeking a 'single male between 40 and 55, who is broad-minded and has exhibitionist tendencies'. The ad asked respondents to generally describe themselves, their interests, and why they considered themselves to be broad-minded and exhibitionist. A couple seeking a single male is highly unusual; only single women or other couples are normally sought. In fact, single men are explicitly told they are not welcome. So, intrigued by both the single male / exhibitionist and potential sexual angles, I answered the ad.
Much to my surprise I received a phone call a week later from Tom, whose wife is Ann (not their real names), in which he said that both he and Ann thought I sounded 'interesting' and asked if we could meet for coffee to become acquainted. My heart was thumping at this point, but a noontime coffee seemed pretty tame, so I agreed. I reminded them that my reply stated I was neither gay nor bi-sexual, and they said that was ok. They would tell me more of what they had in mind when we met.
All three of us were pretty nervous when we met, which I took as a good sign that they were amateurs and their ad was probably legit and accurate. They turned out to be a normal looking couple. Tom was my height, 6'3', with brown hair, and Ann was a 5'4' brunette with shoulder length hair, and very shapely. They were a handsome couple, and they seemed like very nice people. Both were 42, which was 9 years younger then me at the time.
After some nervous preliminary getting-to-know-you discussion, Tom took the lead. He explained that he and Ann had been married 14 years and sex had become predictable, not too exciting, and not very frequent. They had begun renting porno videos in an attempt to spice things up and this was producing the desired effect.
Tom discovered he was turned on watching women give their partners a blow job. He especially liked watching a small feminine hand wrapped around a large, hard cock and masturbating him to climax.
Ann discovered that she was very turned on watching men masturbate, either together or singly, so she favored gay films. She was fascinated by the variety of cocks, circumcised and uncircumcised, and the variety of ways men masturbated, including how they ejaculated 'some shooting long, strong streams and some just oozing out'. Her 'all time turn-on' video showed five guys arranged in a circle masturbating to orgasm. She had heard of 'circle jerks', but had never seen one. Watching them stroke, bring themselves to orgasm, and ejaculate in their own unique ways was a huge visual treat for her. She did not have much sexual experience prior to her marriage, so she was really turned on by the cock variety and how they 'did it'. Except for her husband, she had never seen a man masturbate, and Tom rarely did so in her presence, at least prior to the recent videos.
Their erotic viewing had the hoped-for effect of giving their sex life a major boost. But their newly discovered mutual masturbation interest was what intrigued them. They were now in their 'creative phase of restructuring our sex life', as they put it, in which they were scripting scenes for them to play out that featured masturbation. As much fun and exciting as this was, Ann's big fantasy was to be an observer while a group of men performed a circle jerk.
So, the purpose of their ad was to find one or more men who would be willing to join with Tom and masturbate as a group with Ann watching. Their plan was to initially select only one man to see how things went. Ann felt that watching her husband and 'our guest' jointly masturbating would qualify at least as a mini circle jerk. If all went well, she hoped to add more men so that she could fully experience her fantasy.
They made it clear that sex with Ann was strictly off limits; only masturbation was of interest to them. Since it was her fantasy, Ann would be calling the shots and the 'guest' male(s) would do as directed. Scenes would be conducted at a 'neutral site' -- a hotel suite with multiple rooms and privacy, which would be arranged by Tom - so that the location of each party's home was not revealed. We were to remain on a first name basis, with only my phone number known to them, until they felt comfortable enough to reveal more.
This was not at all what I had imagined, but I was delighted with what they had to say. I liked the fact that they were both so clear about what they wanted and what their limits were. After many more gulps ('is this for real, and do I actually want to do this?'), I agreed to their conditions. Tom said he would call me if they were interested in my being their first guest.
I didn't hear from them for about three weeks, so I assumed I was not the fortunate chosen one. I was both disappointed and relieved, since I was still having qualms about 'what have I gotten myself into?!'. I was surprised to eventually hear from Tom, who told me they had interviewed other men and had decided that 'you are the one, if you are interested'. I was and I was both excited and scared as I accepted their offer. We agreed to meet the following Friday evening. Tom called back the next day to give me the address of a hotel in which he had reserved a suite that would give the privacy we needed. He told me they would pay for the room as well as supply the wine and cheese. I was asked to dress all in black, including black bikini underwear. Wow, this was really going to happen!
I became more and more nervous in the five days leading up to the 'big day'. I had never engaged in any type of group sex with strangers, and I was wondering if I had gotten in over my head. What were their expectations? What if I didn't live up to them? Maybe their expectations were very unrealistic after watching young, hung studs perform in the porno videos. I'm not bad looking and I'm pretty experienced sexually, but I'd never be mistaken for a young, hung stud. What if? What if? What if?
I finally decided that I was making too much of this. After all, Tom wasn't a young, hung (I wasn't sure about the hung part, but I guessed it was so) stud either. And they had seen me, so my looks had been at least passable. I also guessed (correctly, as it turned out) that they were as nervous as me since this was their first attempt to experience their newly discovered sexual turn-on, and they were probably having the same misgivings as I (they were). With a conscious act of will, I put myself at ease and appeared, dressed in black, at their suite at 8 pm on the following Friday.
Tom opened the door and enthusiastically greeted me. Tom, like me, was dressed in a black shirt, black jeans and black shoes. He showed me into the sitting room where Ann was sipping wine. She was quite a stunning sight in her black outfit - cashmere sweater (my all-time erotic item in women's wear), jeans, and high heels. My cock also found Ann very sexy, and registered its vote by beginning to get hard and causing a bulge in my pants. Both Tom and Ann noticed, chuckled, and said that 'it looks like you're ready for an interesting evening'. This initial interaction served to relax us all a bit.
We sipped wine and talked for a while. They reviewed the conversation we had some weeks earlier at the coffee house about how the masturbation theme in the porno videos they were now watching has been a huge turn-on for them and has had the effect of revitalizing their previously stale love making. What they had planned for this evening was to create a scene that would allow Ann to experience her new fantasy of watching a male circle jerk.
Ann was going to watch Tom and I slowly masturbate to orgasm. Since it was her fantasy, she was 'in charge' and would tell us what she wanted as the scene progressed. She was very interested to see how I masturbated since she had never seen another man masturbate. She was curious to compare how Tom and I 'did it' - our body movements, noises we made, and muscle spasming as we orgasmed. She was especially interested to see how we each ejaculated because she had seen a variety of ejaculations in her videos, varying from 'oozers' to 'shooters'. Ejaculation was a big turn on for her, she explained, and she was eager to compare our efforts.
Needless to say, this very explicit discussion was highly arousing to all three of us. We were nearing the end of our second bottle of wine and were quite relaxed at this point. Tom and I each had a bulge in our pants that was now pretty prominent.
Ann took the lead and said it was time for the fun and games to begin. She told Tom and me to stand and strip very slowly. Tom and I did as Ann had requested. It was bizarre stripping with another man in front of his wife, something I had, of course, never done or even vaguely considered! She was smiling broadly as our clothes came off during our slow strip. She let out a little gasp when the two of us stood totally naked and erect in front of her. Her smile and her 'very nice, very nice, very nice' comments made it clear that her fantasy had a good start.
Both Tom and I were very curious about the other's equipment, so we checked out each other's erection. Much to my relief (and probably his), they were similar. My erect cock is nearly 7 inches long and fairly thick at nearly 2 inches in diameter. Tom's is a little shorter and thinner, but shaped about the same. We are both uncircumcised and our cock heads are quite full and large when erect.
Tom's erection is uplifted about 30 degrees and bends slight to his right. Mine goes just about horizontally straight out from my belly. Our balls are about the same and we each have moderate amount of body hair. She was delighted that there was a small, but noticeable difference in size of our cocks, and especially because there was a large difference in the angles of our erections. A few of the men she had watched also had erections like me that stood straight out. She had never seen that before and thought it was 'neat'.
She asked us to walk around the room so 'I can see how your cocks, balls and asses giggle as you walk'. We were not allowed to touch our cocks, but to 'let them dangle out in space'. She asked us to put our hands behind our head and to rotate our hips so that our erections bobbled up and down and side to side. She thought this was great fun. I now realized what was meant by 'exhibitionist' in their ad. It was both an erotic experience to be nude in front of her, and Tom, and to see how much fun she was having as her fantasy was taking place. She kept muttering 'my, my...my, my...my, my' as we posed for her.
She asked us to stand across the room from her chair, and a short distance apart, so that she could have a full body view of the two of us. She then started her own strip, which I was hoping would happen! She slowly removed her sweater, shoes, and jeans. Her bra was a strapless 'shelf' type which exposed the top half of her full and beautiful tits, and revealed a little of her dark nipples. She wore a g-string that didn't fully hide her brown triangular bush. I thought she was absolutely gorgeous and really stunning looking in her brief black attire. She remained semi-nude throughout the rest of the evening.
The sight of Ann stripping and exposing her lush body brought on the hardest erection I have ever had. It was also true for Tom. Even though he knew her body intimately, having his beautiful wife seen by a stranger was very arousing to him. She was pleased that 'I have such a strong effect on you two handsome gentlemen'. Ann was looking across the room at two very erect, engorged and red cocks that were staring back at her.
She told us to start the circle jerk, but asked if we would proceed slowly, making the scene last as long as possible. And, ideally, she wanted us to try and cum at the same time. The excitement of the highly arousing activities up to this moment were initially dampened by our awkwardness. Tom and I had, of course, never watched the other masturbate, so it was a bit difficult getting started. We had not discussed what would happen once we started, so we were winging it as we went along.
Tom had placed a bottle of lube on a table, so we each applied some and began to slowly masturbate. I tensed up initially and was having a hard time getting my head - and cock! - into the swing of things. Tom didn't seem to be as affected by my presence, probably because Ann was his wife and not a stranger, and probably because they had discussed this scene so many times that he was happy that it was actually happening. After a little while, his more relaxed attitude and the smile of obvious pleasure on Ann's face, caused me to relax and to get fully back into the proper attitude.
Much to Ann's delight, Tom and I masturbated differently. Tom uses one hand on his cock and the other on his balls. He kept massaging his balls as he worked on his cock. He stopped occasionally to manipulate the ridge just underneath his cock's head using his thumb and two fingers. This obviously was very erotic for him because his whole body stiffened when he did this.
I use one hand to masturbate and mainly stroke up and down slowly. I'll also squeeze my cock head as it becomes more and more sensitive and engorged. I alternate between lots of very slow stroking and short bursts of rapid stroking. Massaging my balls doesn't do much for me, so I use my other hand to pinch, twist, and pull on my nipples, which become extended and very sensitive when I'm aroused. So, it turned out that Ann was treated to watching two men masturbate in different ways. She said afterwards that she was hoping this would be the case, and was thrilled when it turned out to be as she had hoped.
It's hard to describe how utterly erotic it was to be nude, masturbating next to another man, watching each other 'do it', and with a sexy semi-nude woman watching!
Tom and I were both determined to prolong our masturbation as much as humanly possible, but it was hard because our strip and nude posing had taken its 'toll', making us both very aroused when we began. Our body movements and moans made it clear when we were getting close to the edge. He stopped stroking and held his cock while continuing to massage his balls until he calmed down. I used both hands to fondle my nipples and left my cock alone until my sensitivity also decreased. This worked well for both of us and enabled us to satisfy Ann's (and our!) wish to 'keep it going'.
At one point Tom gave out an 'ah-ha, I wondered when you would get around to that' comment and I saw him looking at Ann. She had pulled down the shelf bra so that her tits were exposed and was fondling them with one hand while the other hand was buried in her bush, no doubt fondling her clit. Tom said to me 'that's how she does it with the video, she plays with herself while watching the guys beating off'. My arousal meter went off scale with that remark and watching Ann watching us.
I have no idea how long this went on, but the 'calm down' period happened many times for both of us. Ann really liked it when I used both hands to fondle my nipples during these times. She moaned audibly when I held both out as far as I could while twisting them.
It was definitely getting hard for each of us to hold back much longer. Our moans were becoming more frequent and louder, our bodies were flexing more, and our muscles were beginning to spasm. Tom said to me that he was close to cumming and asked about me. 'Yes, me too' was my reply.
He grasped his balls tightly and sped up stroking his cock. He held his cock and hand next to his belly, so his cock was pointing straight up. His moans became louder and his body became rigid and straight. He stopped stroking and held his cock tightly while he came with a sustained moan. My 'finish' routine is to keep stroking at a moderate speed until I begin to cum and to continue stroking more slowly until I'm finished. I hold my cock straight out or at a slight upward angle. My upper torso bends slightly forward just as I'm about to let go. I utter a string of 'uh, uh, uh' sounds while I'm cumming.
Fortunately for Ann and her fantasy, we did reach climax and ejaculate at the same time. Ann was absolutely thrilled that, in addition to masturbating differently, we also ejaculated differently. According to her description afterwards, Tom is an 'oozer', and sends out a steady flow of ejaculate that oozes out of his upright cock and flows over his hand and balls. I, according to Ann, am a 'gusher and pulser', and send out pulses of ejaculate that shoot out in front of me at decreasing distances until only a small amount oozes out at the end over my hand while I'm slowly stroking.
Both Tom and I were now gasping for breath and weak in the knees. We each found a chair and collapsed in it to recover. When we became 'conscious' we could hear Ann moaning and looked over to see her legs spread and the g-string pushed off to one side. She was rapidly rubbing her clit with one hand and fondling her tit with the other. Her eyes were closed and her head was back. Her moans turned to rapid breathing, with a sucking sound, and her legs tensed as she built up to her orgasm. The sucking sounds switched to a low steady moan as she climaxed. She then let out a 'whew', opened her eyes in amazement for a moment, and then went back to fondling her clit again. She had two more orgasms like this, and then fell back into the chair as spent as we two were.
She - and Tom! - never knew she was multi-orgasmic until their recent sexual 'restructuring' began. They were both surprised and pleased that she was capable of multiple orgasms, like the three she just experienced.
Tom somehow found the strength to pour us another glass of wine which we gratefully accepted. We sat in our separate chairs both amazed and stunned at what had taken place. Not much was said, as we were lost in our thoughts, except for an occasional 'wow', 'amazing', 'can you believe that?'. Ann then announced 'as fantasy director I am calling an official end to our scene, let's get dressed and reconvene for a discussion'. She also asked Tom to order sandwiches and coffee from room service. Nice touch I thought.
Tom and I were the first back. Our eyes met and we both broke into wide grins and chuckled, which turned into laughter. Ann walked in to find us both breaking up and she, too, began to laugh. It was a great and natural way to decompress. The sandwiches and coffee arrived and were very welcome.
I couldn't stand it any longer and asked Ann if she felt her fantasy was fulfilled. She gave an enthusiastic 'yes!' and was very pleased that it turned out just the way she had imagined and hoped for. 'Two handsome men, with nice bodies and beautiful cocks, willing to go along with everything I asked for, different masturbation techniques, different ejaculation types, aroused to the point where I had three powerful orgasms - what more could I ask from my first circle jerk!'.
She complimented us on our slow strip, and told us what a turn on it was for her to see us both naked and erect. She was really turned on by how our cocks hung and loved the contrast between Tom's uplifted erection and my horizontal, stick-out-straight erection. 'Sitting down I was looking right into the face of your cock'.
I told her I enjoyed watching and listening to her cum. In my experience, women are very different with the sounds and body movements they make when cumming. So it's always fascinating to see how a woman reacts. Ann basically 'talked to herself' as she approached orgasm, and then let out that delightful 'whew' when she stopped spasming. I liked the way her progress could be monitored by her sounds.
We agreed that this experiment was a great success, that we liked one another, and wanted to do it again. They were going to give some thought to the three of us trying this again, with variations, or possibly repeating the same scene but adding another man. Ann loved her first exposure to male variety and wanted to give serious thought to increasing our group. 'More cocks, more orgasms, more ejaculations, yummm' was her comment. I shortly left them in their suite and Tom said he'd call me within the week.
As Ann would say, 'whew!'.
There were more scenes in subsequent months and I would be happy to describe them if there is any interest.