'Letter To An Admirer'
By Jennifer James jennyjamestg@hotmail.com
Dear Michael
It was on a Saturday and I'd been going through a week's worth of emails that had backed up. I quickly deleted the spam and gone through the correspondence from my friends and acquaintances, and I'd saved the new emails till last.
There was an introduction from a new local crossdresser, with a typical picture of a 'girl' with visible beard stubble and hairy arms in a bad wig with uncut bangs pushed to the side, a micro miniskirt, a spandex top highlighting the belly and back fat, and garter stockings with thick leg hair showing through and on the upper thighs. I get those all the time with the 'girls' telling me how passable they are and invariably they either want to hook up for sex or go shopping at the mall. This particular 'girl' wanted to do both and I sent a quick reply back that I didn't get intimate with other girls (which I don't, ever, even if they don't have hairy arms and legs and beard stubble) and if they were looking for friendship I'd let them know when I was going to be out socializing in a gay bar and they could join me for a drink. Pretty sure I wouldn't get a response back because the sex had been their primary motive.
There was an email from a guy that said: 'Hi, I saw your picture, you're beautiful, let's get together for fun' That was it. No statistics, pictures, anything. I sent one of my stock cut and paste replies that said: 'Some basic stats would be nice, but I don't meet guys for quickie sex' Knowing I probably wouldn't get a response back from that one either.
Another guy had written: 'Hi Jenny, I saw your ad and stunning picture and had to write. I'm a very oral Bi/MWM, 44, 5'8, 240, looking for a discreet meeting with a girl like you. Please let me know if you're interested' Again no picture, but 240lbs. at 5'9 is way too heavy for me, the Bi/very oral comment most likely meant his main interest was in my cock, And the 'D' word always raises a flag with me. There's nothing inherently wrong with the word discreet, I always use discretion and there are places to meet, like gay bars or out of the way places, that are very discreet. But when written up front like that it invariably means the guy wants to meet in a hotel room-only situation. For safety reasons alone I don't do that but I've also spent too much of my life already in a closet to want to stay there. I responded anyway with another cut and paste reply I frequently use: 'Hi, You sound nice but I only meet people in public. But thanks for writing' And a response from him was unlikely as well.
And lastly there was your email...
Yours was different than the others. No picture, of course, but you had started right off with stats. 5'11", married, 49, brown hair and brown eyes, and a mustache. And after writing that you'd seen my picture and profile at URNotalone, you said that you'd visited my web site and actually read it and not just looked at the pictures. And were wondering if I'd be interested in talking further.
I was, of course, and wrote back and told you so. But right upfront I mentioned that I wasn't interested in quickies and only met in public. And I figured the odds of a response after that were probably less than 50-50.
But you did respond back, and this time you told me more about yourself. Your interests in literature and music (of which we had much in common) and your interest in sports (of which we had nothing in common since I have no interest in sports of any type) And at the end of the letter you asked me, if we met, where I'd like to meet.
My response to you talked about some of my general likes and dislikes and what we had in common. And I told you I was comfortable meeting anywhere you felt comfortable, maybe for dinner. And I asked where your interest in transgender started.
Your next email was again conversational to start, and you told me you'd had a relationship some years back with a T girl that had gone on for some time casually. And you said you'd had a mild interest in transgender since your teens but your main attraction to T girls was their femininity. You liked makeup and sexy clothes on women, and that your wife had gone the other way after childbirth and that intimacy with her had pretty much vanished. And you suggested we meet after work some Friday at a hotel bar halfway between us for a drink and that we'd figure a dinner spot then.
But now was the tough part ... my schedule was a mess and hard to plan anything - which wasn't typical but was a reality at that space in time, and your schedule appeared to be about the same. So for the next few weeks we kept comparing calendar's to come up with a date that would work for us both, and continued to talk about a lot of things. I finally had a Friday open and told you about it, and you said that it seemed like a good night for you as well. But a few days before you wrote to tell me things had changed; you would be able to get out that evening but not for the entire night. Unusual for me, I agreed to meet you at my regular club where I don't take guys, but under the circumstances it seemed OK, so we agreed to meet there for dinner on the Friday, and when you had to leave somewhat on the early side I'd have a place to socialize till the night was over.
That Friday I got ready to meet you, and as we weren't going to be meeting mainstream I dressed differently than I would have. I wore a slip dress with 4-inch heels and maybe a little more makeup, as opposed to wearing the capri's, low heels, and lighter makeup I would have worn to a hotel cocktail lounge. And when I walked into my club and my friends saw me many commented positively on my appearance that evening. But minutes after I walked in you called me on my cell phone and told me you were running late and that I shouldn't wait for you for dinner, but that you would be there about an hour later than expected. I ordered dinner and ate with my friends, and socialized till you got there.
When you walked in I was talking to a lesbian friend but I knew it was you right away - you looked somewhat lost till you spotted me at the bar and came over. I took my drink and moved to a table on the side and we sat down. I thought you were cute if not handsome, with a nice smile, and as we started talking the conversation was easy.
But very quickly your eyes kept going from my face to my legs, and looking down I noticed that you had developed a large bulge against your zipper. And not 15 minutes later I saw you looking at your watch and I asked what time you had to leave. You told me that unfortunately you were going to have to return to work that evening. And then you asked if I'd like to go somewhere quieter to talk, maybe my van? (Which I'd mentioned I'd had in the emails, as a point of reference for when we met.)
I honestly didn't know what to say. It was way too early, in multiple ways, for anything sexual. But when I looked down at your bulging cock I realized I wanted that. And despite knowing better, I agreed and we left the club and went to my van and sat in the back.
You leaned over to kiss me lightly, and I kissed you back, and as we sat there touching lips and tongues I felt your hand on my bare shaved thigh and I reached over and laid my hand over your bulge. We continued to kiss, and your cock grew rock hard under my petting, and a few moments later you reached down to open your zipper and your cock sprung out. I reached down to take it in my hand, and with the first stroke down your shaft and over your pronounced mushroom head I felt the precum that had already started oozing out. But before I could lean down to lick it off you slid your hand under my dress and slid my cock out the side and took that in your hand, and quickly slid to the floor and leaned over to take me in your mouth.
I was immediately disappointed, having hoped you weren't interested in that, but after only a few wet strokes with your mouth you were back up next to me on the backseat where you quickly slid off one shoe, pulled your pants all the way down and off one leg, and leaned back on the seat with your knees spread wide. I slid to my knees on the floor facing you and leaned in for a kiss and then leaned down and took your cock in my mouth, tasting the precum that was there waiting. I sucked gently on your cockhead for a minute and then slid my lips all the way down your shaft slowly till your cockhead was in my throat, and then slowly came back up, and down again. You moaned right away and said 'Stop, it's too soon'
I stopped completely and leaned in to kiss you, and for a few minutes we kissed, and then I leaned down again and this time kept my mouth very soft on your cock, again tasting the precum dribbling out. I licked and sucked gently without using my mouth to stroke, but within seconds you again moaned and told me to stop - and again I did.
We kissed again softly for a few minutes but you soon stopped and leaned back. I reached down and gently took your balls in both hands and softly massaged them, and leaned over towards your cock again. I slid my lips all the way down your shaft, enveloping your cockhead in my throat and held it there and you moaned, but I knew you wouldn't stop me this time so I started moving my mouth up and down your cock slowly, using suction with my tongue pressed against the underside of your cockshaft. And on the third stroke when you said 'I'm going to cum' I slid my mouth out to just encircle the end and sucked and licked across your slit, and within seconds I felt a pulse against my lower lip just before you exploded into my mouth and the first spurt splashed against my throat opening, followed by another, and another, as your sperm flowed into my mouth hot and pungent. And as you screamed almost silently I drained your balls of their last drop of cum and swallowed it down, and as I felt it sliding warmly and thickly down my gullet I stroked a final drop from your cock and leaned over to lick it off.
You collapsed back against the seat, drained, and I moved up off my knees and over next to you on the seat. I leaned over and kissed your lips, but you didn't return it so I leaned back also, and after just a minute or two you leaned forward and began to pull up your pants and said you had to go.
Not surprised, I straightened out my dress, and took my purse and began to comb out my hair, which wasn't very messy, and fixed my lipstick, which wasn't bad either. You told me it had been great, and that you'd write me on Monday and hopefully we could get together again, and not have to rush things next time. I opened the van door and let you out, a quick kiss on the lips, and you were gone across the parking lot - and I was soon back inside the club, talking to friends just like I would have been had you not shown up that night.
But the taste of your cum lingered in my mouth and throat for quite awhile.
When I didn't receive an email on Monday I wasn't surprised. And by the end of the week and still no mail I wrote you off as another one of the many guys who played your games. But when the following a week I got your last email I opened it right away, more out of curiosity than anything else to see what you had to say. And found the usual apologies for not writing sooner and the obligatory 'Had a great time' - followed by hopes that we could get together again and maybe the next time I could drive over to where you worked and we could meet in a parking lot.
If I wanted to meet a guy in a parking lot to suck his cock there's nothing easier, I get those offers almost daily. And if you had been upfront about that being what you were looking for from the beginning - and willing to meet me somewhere I happened to be passing anyway, at the time I happened to be passing there anyway, I most likely would have stopped off regularly to open my van door and have you sit on my back seat and drop your pants while I kneeled on the floor and sucked your cock till you exploded in my mouth. And afterwards all I'd have expected was for you to pull up your pants and leave quickly so I could get back on the road heading towards wherever I happened to be going that night. Until the next time you wanted to relieve yourself in my mouth at a time and place convenient for me.
But I'm not into games - so I'll let you play your games without me.
Jenny
Please write if you like the story jennyjamestg@hotmail.com