Letters Vi Continued

I don't have those old stories, but like so much of my "sex life" I have the memories. Reading your comment was thrilling. I'm amazed at what turns me on now. I was fully aroused by the time I'd finished reading it.

I know it's strange, even stranger to write it out loud like this, but it feels better than any physical intimacy I can imagine having. When I was younger, my only pursuit was to figure out what she wanted, I focused solely on making the woman I was with feel good. Jacqueline was the first woman that made me feel good, and she did that by dressing me up as a woman and treating me like a lesbian lover. Her making me feel that good was inspiring and thrilling and made me want to please her.

We were both 25 and we'd watch lesbian porn, at the time, I'd thought she was watching it with me because I liked it. I did like it, I still do, but it wasn't until we'd met again 10 years after breaking up that I'd learned she was the one aroused. We met up in Vegas and she admitted she fantasized about being with another woman. We dressed up in stockings, lingerie, panties, and makeup and I painted her nails, bathed her, and then she mounted me. She had me lay perfectly still, straight, and flat out on my back. She had me keep my legs closed, my arms close to my side, and hands flat along the sides of my thighs and she took my erect penis and slipped it into her hot and wet vagina and laid her body in a mirror image of mine and squeezed me between her legs until she came on top of me.

It was the strangest sex I'd had up until that moment. I was unable, not allowed to move or touch her, and she pushed her hips down onto me. She was begging me not to say anything, not touch her, to just let her use my body. Her body was like a rapidly inching caterpillar pressing me deeper and deeper into the mattress until I couldn't stand it any longer. I remember begging her to fuck me. "Cum on me Jackie, cum all over me and fuck me, fuck me, fuck me." I was like the woman, and she was the man.

(a)t fhat time in my life, I'd never encountered a woman who knew what she wanted. She knew what she wanted and she liked to play, she had a vivid imagination.

If I could meet a woman like that now, I would enjoy intimacy with that sort of woman.

When I was 25, she taught me how to help make a woman feel good and I was addicted to it. That's all I focused on thereafter. I never orgasmed unless the woman did first. I mean in my relationships. I did have a few flings and those were different. In a fling, you don't really have time or knowledge of the other person to know what they want or how to help. You try, you seek, you do your best, but unless the effort is reciprocal, it makes it difficult to achieve mutual satisfaction.

(y)et, there was Grace, a Canadian rebound I dated after Maria, but she had no imagination. It seemed like she just wanted me to finish. I dated Toyoko, a Japanese woman for a while, but we never figured anything out either. I think some women just like to get fucked really hard and that's all they want or need. I can't just fuck a woman, I have to want her, I have to be teased and denied until I can't restrain myself. Sex with Jackie and Maria was fun and fresh and exciting. Jackie and Maria, we definitely fucked hard, but that was because we could tease, and play, and build up the tension. We took our time and played until we were both feeling so turned on that we had to fuck.

That kind of sex comes from intimate knowledge, and a desire to please the other person. Michelene and I had that, but we never even got naked together, the closest it ever got was one time in a hot tub and we were in swimsuits. I orgasmed with her grinding her bottom against my crotch. The water was hot and bubbly, but I am convinced she knew I'd orgasmed, but she pretended she didn't know. I remember her kissing my face all over after I'd spasmed against her. She kissed me all over the way a woman does after she has an orgasm. Maybe she'd had one too, but I was too overcome with lust that I didn't notice it.

(a)lso, when Michelene and I kissed and made out, I was like a Navy Seal team, assaulting her with every subversive attack on her libido just to get her to kiss me more deeply, press her body heavier against mine, spur her to use her tongue behind my ear or paint my lips with. I would leave her house in pain from arousal. If she'd have let me I would have and could have carried her around on my hard cock like it was a metal fork and she a piece of meat.

Those were my pursuits. I loved doing whatever I could to make a woman feel good. Ultimately I was hunting their orgasm. If the woman was interested in guiding me, interested in reciprocating, then I would fall in love with her and then a fling would turn into a relationship. Otherwise, the sex wasn't worth it, and I would move on, or she would, and that was that.

Now, if I could find someone like that, I would pursue it. But I'm enjoying masturbating just as well. I look forward to my every-other-Friday evening masturbating and writing stories. And when I see your comments, or I know that you've read a new story, it's all I want. I absolutely lose myself in my mind. I watch my old clips or look at those pics you sent me and absorb myself in fantasies of you.

when I watch myself I personify your voice, your body, your mind onto my own psyche and I talk to myself as if I'm you. I touch myself and imagine it's you laying beside me talking to me and telling me what to do, how to touch, and what to say.

Do you remember the site where you made the profile that we shared? When I was in Berlin and we hatched a plan to find another sissy for me to play with? I have a profile there if you want to see some of the stuff I saved. ((I'll tell you how you can visit me, look for 'scranton', it's also my username; look in my most recent comment for how to get the p-word) I set the profile so only the owner can see what I've posted))

When I saw your comment it was all I needed. I orgasmed so quickly, I couldn't help myself. I tried to stave off the intense feelings of arousal but couldn't. I was hard again in a matter of minutes. I reread the letter in which you commented repeatedly putting myself in your shoes. I wondered and searched for aspects that may have been a turn on for you. Was it the public exposure? I think that may have been it, although I wished it was the part near the end, when I describe how I masturbate thinking of you, saying your name aloud, alone, in the dark in my bed.

(l)ast night, after I came so fast, I cleaned up, took a shower and cleaned up and depilated my lower body, not the legs, I don't do that any more. But I keep my crotch and ass smooth and clean. Shaving my legs is too risky and would raise too many suspicions. I was hard during my shower and the hot water and slippery soap reminded of me of how I used to prepare for you, it was like you were there again. I felt so tingly and excited as the underside of my hard cock slipped in and out of the palm of my soaped up hands. I cleaned my asshole, my pussy I called it. I spread my legs and leaned my head against the shower wall and fingered myself calling out your name, repeating it over and over, yes, I said, yes, like that, finger me just like that.

(a)ll of it came back, the only thing missing was the bath I used to take. I would put candles up all around my flat and in my bathroom and with a glass of whiskey and ginger ale, I would soak in the tub and stroke myself just enough to keep myself hard. I miss that old bathtub. I miss the whole flat smelling of candles and my mind clouded with weed and whiskey. Like a trance. It felt just like that last night.

I'm writing this on the train. I'm heading into Prague to look at an electronic drum set for my son. He's taking up the drums. I remember how I used to go out with you in Berlin. I would dress up after a long evening at home performing my ablutions. I would wear my sport coat and slacks and walk to the nearest metro smoking a joint, the feel of silk and nylon on my body in the coolness of the night. I'm just wearing panties now. I have only two pairs now. I ordered them online, size 9 queen, Vanity Fair's, one pink, the ones I'm wearing, and one pale blue. They are big and swishy and I adore how they make me feel.

After the shower, I set up my bed with my big pillow positioned in the center and two big pillows at the headboard for me to lay against. I lay down in bed and spread my legs around the pillow at the center of my bed and opened myself wide. I slid my vibrator into position so it pointed straight at my perineum and I lowered myself down onto it. I turned it on medium-low and read the letter again and again.

Sometimes, like last night, I will visit users who've liked or followed me and look at other stories they like and see if I can find something intriguing. A new user started following me after you'd left your comment and I went through some of their favorites. I found one about a timid young man who gets milked by an older woman who liked him to call her mommy. I have been enjoying this genre of story lately.

(b)ut it's not that I fantasize about my mother, it's the type of woman, the things she says, the way she treats them with such love and tenderness that arouses me. She is encouraging and she accepts their needs and desires. I always see you in the stories, not just these, but any story that turns me on.

Like in the public exposure fantasy. Where you silently encourage me, your effort is minimal and simple. You only need to show me. Just reading a book or browsing your phone, sitting on a park bench with one foot up on the seat of the bench, your other foot on the ground, your legs slightly spread and your skirt hiked up just enough to allow me the perfect vantage. I am staring at your soft, damp panties. I'm staring at your soft rounded mound pressing against the satin silk of your panties. I'm staring at your tanned thighs, darkened by the shadow from your skirt. And your tacit agreement lets me stroke myself. You don't mind that I'm taking my time. You don't mind that I am making this last. You don't even watch me. You just know I'm stroking myself, edging for an hour or more, and as the peaks and valleys of my masturbation session pour forth sperm and precum you expect that I'll indulge in licking up all of it.

(l)ast night after an hour of this I hit this stretch of arousal, between my thoughts and the increased power of my vibrator which had slipped down and was pressing into my pussy, I was on the verge of orgasming but I denied myself and let go of my cock and began fucking my vibrator. It began to enter me and I fucked myself with quickly increasing thrusts and I felt my sperm sliding up my shaft and I clenched my crotch and pussy closed just in time for two, three, and then a fourth shot of sperm and I grabbed my cock to shut off the faucet and in my other hand caught my fresh warm sperm and devoured it, going back for more until I'd cleaned myself fully. I remained hard and aroused and I let go of my cock and slipped my vibrator past my pussy ring and held it there deep inside me moaning your name over and over, lowing yes, yes, yes until I'd come back to earth. The act of denying myself a full orgasm and licking my fingers clean of my sperm was shocking and surprising. I was still very hard and turned on. I wanted my cum. My fingers were wet, my mouth was salivating, and my asshole was filled with my vibrator. I sighed deeply and my head seemed to buzz and I returned slowly back to the story I was reading about the woman who wanted her boy-toy to call her mommy and to beg his mommy to milk him and who wanted him to eat his own cum as a way of demonstrating his devotion to her and I let myself be that boy-toy and I inserted you as the woman who wanted me to do these things for her.

(u)sually, when I masturbate, first off, the boys are never with me. I never have the need to do it when I have them, and since we have shared custody, 50/50, I only masturbated 50% of the time. The only time I have these kind of sessions are Friday nights when I don't have the boys. Otherwise, if I do masturbate it's just to get it done so I can sleep. It maybe takes 20-30 minutes. Last night was great, like I said, the first one was quick, under ten minutes. The second one was over an hour, if you include the shower then 90 plus minutes. Today is Saturday and I've been writing this story since this morning, in between work for school. Now I'm on the train to Prague to look at the drums. I want to have the story done by tonight. So when I get home, I'll sit in my panties and write. I might get a little pint of whiskey for old time's sake, and then I'll masturbate and proof the story, make small edits, all the while stroking and playing with myself, trying to spot the aspects that will draw your attention.

All of my life I spent pursuing female orgasms. My big fear was that I'd be a terrible lover. I made sure that wa never the problem. Actually, it did become a problem because many of my relationships went on too long because the woman liked having sex with me. Take Debbie for instance. She fell for me but it was because of the sex I'm certain, I'm not a very good boyfriend or husband for that matter. With Marcela, I was able to pretend for a long time that she turned me on, but after a while, she was just too boring and we stopped having sex. I tried. I really did try to get her to understand foreplay but all she ever said was put it in my ass. I can appreciate that, I know it feels good, but she didn't want to play or tease or anything. When I tried to get her to understand that, she would try to give me oral, thinking that was what I meant.

After the divorce, I just had no interest. I had all of my memories of you, Jacqueline, Maria, and even Michelene to lean on. I didn't need an actual person. I reached out to Jacqueline and Maria both since then. Jackie has sent me some photos over that time, Maria told me not to contact her again. I've even written a couple stories for Jackie and she liked them, and wanted more. You might have read them on my literotica page, "Woman, shemale, sissy playtime" is one of them. There's another one on there too, where the woman character grows a cock and balls and I grow breasts and a pussy called "My Metaphor." She liked that one a lot. I love writing stories for her, for you, and back when Maria still wanted to talk to me, for her as well.

(e)ventually, as the pain from the divorce dissipated and my reliance on alcohol and weed dissolved, I became more clear and able to control myself. Like I said, my masturbation has decreased to a mere percentage compared to what I was doing and now I don't drink at all really, and I only indulge in edibles on weekends when I've got an extra day or two off to go along with the Saturday and Sunday.

I actually like watching futanari porn on xhamster now too. There are these great ones where the woman uses her son and her son's friend for her pleasure. The same series includes episodes where the son and his friend become sissies and the mother has them make out with each other while she uses them like toys.

(8) I think now that I'm older I just want to have sex that makes me feel good and that I don't have to feel responsible for another person's pleasure. Sex with another person sounds too complicated and carries too many superfluous connotations and contexts. When I was young there was one goal, feeling good. Now, people my age carry too much baggage, you can't just have a throw in the sack.

(3) I'm on my way home now. The drum set looks good and I'll go back tomorrow morning to pick them up. The boy will be happy and so will I. It's simpler like this, without a wife to demand her way about everything. I can make a simple purchase for my son. I can find the drums, go look at the drums and then go buy the drums. I admit, I wish Marcela would have been a better fit because it would be nice to be a whole family. But no amount of hoping and wishing could have made our relationship a good one and I would not want my boys to grow up with us as a role model for them.

(1) I will go home tonight and play. I bought new batteries for my vibrator. If you follow the clues I left in the comment on the letter you can come see some clips you may not have seen. I hope you liked this letter. I can't wait to get home.

I'm home now and making some final edits. I hope you like it. I would love to write something for you, something you fantasize about, but only if you want me to. Until next time.