Married Man Seeks Hung Panty Boy

I placed an advertisement on craigslist. This was the first in a series of mistakes. I am 23 years old and in law school. And straight. But I have always had this fascination with being a third to a married, older couple. There are psychological reasons that seem plausible but this probably isn't the forum to discuss. I never had any luck with the ladies on account of a severe case of the shies and nerdies. But I placed the ad anyhow. I am certainly no expert in this realm but I have gleaned from reading similar postings that there seems to be an interest from some couples in men that are . . . well . . . endowed. And while I am not quite 5-10 and on the south side of 150 pounds, God, in his usually jokey manner, decided to give the geekiest guy on the block a ten inch cock. Not that anyone ever sees it but me.

I received a few replies to the ad but only one that was remotely thoughtful. He said that he and his wife were interested in this sort of thing but wanted to meet me in advance to discuss a possible 3-way dalliance. They were in their early 40s. His name is Jeff and his wife's name is Sylvia. To that end, we decided to meet for a drink which turned into quite a few drinks. And I am not much of a drinker.

Towards the end, he admitted to being cynical about my claimed endowment and this is understandable, I suppose. I don't exactly look the part of a stud! If I hadn't been for the margaritas, this might not have seemed to be a good idea but I thought it reasonable at the time. He suggested we make a quick stop at his apartment, which was empty because his wife and kids were at their beach rental (he had stayed behind on account of work pressures), so that I could prove my genuineness. He said if I stripped down to my underwear, he would be able to tell and that would be proof enough. You can't imagine how awkward this was - in his apartment waiting to be evaluated. He saw that I was nervous and offered another drink which I gladly accepted.

He didn't reference the reason we had gone back to his apartment for an impossibly long time and then said 'let's just get this over with' which felt like a relief. I took a deep breath, stood up and lowered my jeans. He had a confused look on his face before expressing disappointment that I had on boxers that weren't exactly telling. I don't know why he expected me to be in briefs. He said he was also a boxers guy but if I put on something more illuminating, we could put this issue to rest. I am horribly embarrassed by what transpired but, strangely, also acutely aroused. I can't bring myself to tell the tale but his email to me a couple of days later is revealing. Please see below. He had emailed previously, but I had ignored him. Also, let me know what you think of his fantasy.

Dear Kyle,

"Eroticism has its own moral justification because it says that pleasure is enough for me; it is a statement of the individual's sovereignty."

Mario Vargas Llosa

I can only guess at your confused and conflicted feelings and attribute them to your lack of response. You were lead down an unexpected path by someone you trusted. My persistence got the better of you. My limited success in business is on account of this persistence and persuasiveness but it may have been unfair to to use these techniques on you, a relative innocent. Accordingly, I wish to end all coyness and pretense and tell you exactly what I want of you. I would ask that you give the idea due consideration and revert back after you have had an opportunity to deliberate with a calm mind.

Over many years, I developed this erotic scenario that has never been acted upon until, to an extent, our meeting and your visit to my condo. While I did want to see if you had the endowment that you claimed, I also wanted to flirt with the scenario mentioned. I was woozy with anticipation when you were in the bathroom not knowing whether you were willing to fulfill my exacting request.

And, Kyle, when you emerged wearing only Sylvia's panties and a bemused look upon your face, you did not disappoint. You have the BIGGEST and most BEAUTIFUL cock I have ever seen. It is not only lengthy but impossibly girthy and, more importantly, it is smooth, youthful and gorgeous. You were truly blessed and I am glad you choose to share this gift with me. And you may have sold yourself short by advertising ten inches. I suspect it is in excess and, next time we meet, I could provide a more precise measurement if you would allow. This scenario involved you before I knew you existed. Allow me to place a (*) following any particularly critical portion of the scenario. The participant was to be young, intelligent, possibly sexually inexperienced, straight, massively hung*, shy or, at least, on the quiet side and reluctantly indulgent*. When I first read your ad, I KNEW there was a possibility and I couldn't help myself from contacting you.

So now that the veneer has been pulled away, when next we meet, this is what I want from you:

I will leave your name with the doorman and he will let you up. If you don't recall, I own the apartment on the top floor facing south. The door will be ajar and I will be inside on the couch sipping a glass of Teroldego. You need not speak to me or acknowledge me when you enter. You will proceed directly to the second bedroom, strip naked, put your clothes and shoes out of sight and put on the sleeveless white leotard that will be set out on the bed.* Sylvia utilizes the garment when she practices yoga. Of course, it is accompanied by panties, a brassiere and shorts when she wears it. You will not have these accompaniments. You will be nude but for this thin and semi-translucent leotard. It will be tight, Kyle, particularly in the crotch area.

And then you will join me for wine. We can talk for as long as you'd like. I will try not to be obvious about it but I will be admiring the impressive bulge you are sure to cause in the garment. I would like for you to sit across from me and converse as if you were fully clothed. There will be a spray bottle filled with water on the kitchen counter. At some point I will ask that you collect it and bring it to me. You will stand before me and allow me to mist the garment FRONT and BACK until it is clinging to your skin.* If you are not fully erect at this juncture, which I expect that you will be, I would need you to, while standing directly in front of me, manipulate yourself through the wet material until you are completely hard. I will then apply some additional spray water to your crotch. We continue to talk and drink wine but I won't be able to take this teasing much longer.

When I would tell you so, you will get up and go into the master bedroom and close the door. On the bed will be a pair of black thigh highs, a pair of minuscule black lace panties that do not stand a chance of containing your immense cock and a near indecently short black miniskirt that Sylvia hasn't worn in years. Each of these items was purchased and worn by Sylvia.* All will be laundered but lightly sprayed with French perfume that is not Sylvia's.*

You are to remove the damp leotard, place it under the bed and put on the outfit that has been set out for you. I want to dress you up like a WOMAN, Kyle. A woman with a colossal cock wearing my wife's intimates.* You can open the door when you are ready. Take as much time as you would like. The overhead light will not be on but the two sconces opposite the bed will be but dimmed. Sit yourself on the edge of the bed.

I will come in with two glasses of wine, we can continue to talk but, before long, I will be unable to keep my hands of you. I will try to touch your stockinged legs. I will beg you to let me massage you. I will tell you how generou$ I can be. I will try to persuade my way into your miniskirt by any means possible. But you can resist me. Verbally and delicately physically..* Be the virgin on a first date with and older and lecherous man. Resist me for as long as you are able.* I could play that game all night. But then, if so persuaded, allow gradual and incremental touching. Until your entire body has been massaged except for what is confined in your flimsy, black panties. Until your stocking have been pawed so that they no longer sit evenly on your thighs. Until I convince you to allow me to flip up the miniskirt as you are on your back on the bed and allow me to slide the panties down until they are touching your stockings.

And then I would take your hard cock in my hand, Kyle, and slowly and sensually play with it until you can take no more. As deliberate as I was the other evening, I will be even more so. I will say naughty things to you. You will acknowledge how hard you cock is in my hand. I will place one hand near the top of your cock and slowly slide your foreskin down so that the glowing, swollen head is fully exposed. I will beg you to allow me to slide it into my mouth. I wanted to do this the other night, Kyle, but didn't want to risk spoiling the moment. I will tell you how good it will feel. You can verbally resist if you must but when your opposition ceases and you moan out, I will know what you want even though you can't bring yourself to say it. And my hands, lips and tongue will tease and please you until you are shooting cum everywhere.*

So there you have it. It is all out in the open now. Please consider this request from a friend. Kyle, before I conclude, I have to say that two things from the other evening were unexpected surprises that have caused me to masturbate many times since. First, when your cock was in my hand initially you were stone silent. Then, in time I sensed your breathing getting short when I would touch you in a certain way. Then there was a subtle groan that caused me to instantly erupt in my trousers. And then the small sighs and moans that continued to get bolder the closer you came to orgasm.

That brings me to my second and final point. Kyle, I have looked at my fair share of internet porn but I have NEVER seen a person cum that much. The first blast was a shockingly powerful and thick stream but every time I thought you were empty, out came another and another hot and sticky spurt. I have never milked a cow in my life, but I imagine that is how it would be. My hands were covered. Your chest, stomach and crotch were covered. It was ALL over the couch when you left but I was all too happy to clean it up.

Your friend,

Jeffrey