Jill & Me Together

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Making love, just me and a beautiful TS.
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Boxlicker101
Boxlicker101
3,138 Followers

Last week I had a date to go and see Jill, a beautiful transsexual, and Mary, her friend and roommate. They have shared an apartment ever since Jill's parents, who despised her way of living, kicked her out of the house on her eighteenth birthday. They still think of her as male, which she was at birth, but I believe there are more important factors than what a person's sex organs look like and have always thought of Jill as a sweet and lovely young woman. Because of hormone treatments, she even looks more like a woman now and no longer has any need to wear falsies.

As usual, we were very glad to see each other, and once we were inside the apartment and the door was closed, we hugged and kissed with both lust and affection. She was wearing a t-shirt and no bra and I noticed, as I hugged her, how well the treatments were working.

"Your breasts are really filling out. The hormone treatments seem to be working really well."

"Yes, thanks, they are. I feel more like a woman all the time." Jill removed her t-shirt to show me her burgeoning breasts. Although still small, they were very well-formed and topped by adorable pink nipples.

"Jill, you have been a woman for as long as I've known you and before then too." To accentuate this fact, I cupped one of her new breasts in my hand and started licking her nipple. It felt good to my tongue, just like all the women I have licked in the past.

She had some bad news too. "Mary won't be here today. Somebody was sick where she works and she couldn't get the afternoon off. Maybe I should have called to tell you. I hope you don't mind."

"No, I don't mind. I would have come over to see you anyhow." That was the truth but I didn't know just how things would work out. Jill is a woman in every way but one. Instead of a pussy, she has a cock. Usually, when we make love, I fuck her ass, which she calls her pussy, while Mary or somebody else sucks her off but I could see we would have to figure out something else that day.

"We can still use her bed, though," Jill told me, taking my hand and leading me there, after I had removed my shoes and socks. Mary has the larger bed of the two in the apartment, and that is the one we always use. There was a towel, which I would be using later, lying on the foot of the bed.

Naked above her waist, she was barefoot and wearing a short skirt, showing off her pretty legs. Underneath the skirt I knew she was wearing silk panties, and we would both enjoy it when I knelt behind her and pulled them down over her smooth, shapely ass. Jill never wears jeans or anything else that isn't ultra-feminine. She even sleeps in a silky negligee. When she lay on the bed, smiling and reaching out her arms, I knew she wanted me to spend a long time pleasuring her breasts. That was great, as far as I was concerned because I had enjoyed the brief contact with her nipple and wanted more of the same. I removed my shirt and joined her.

After kissing her mouth, eyes and throat, I cupped a hand under either breast and started licking her nipples. After a few minutes of moving my mouth between them, they were erect and Jill was cooing and squirming on the bed beneath me. Apparently, the hormone treatments, besides causing her breasts to swell, were making her nipples more sensitive as well as larger. Both of us took great pleasure in the feel of my tongue caressing them and her pink areolas and we continued for a long time.

Although Jill's breasts were small, they were large enough to be a pleasant mouthful and I drew the soft flesh of one into my mouth to suck on it. My lips formed a seal while I sucked, while my tongue continued to caress her nipple and puffy areola. I was really glad she was taking the hormone treatments because they enhanced her pleasure so much. Although I was also enjoying her breasts being in my mouth, my main goal that day, as always with one of my lady friends, was giving as much sexual satisfaction as I could. That is one of the ways I derive my own greatest pleasure.

I spent another long time sucking on her breasts, once again alternating between them while Jill continued squirming under me and cooing happily. "I really love what you're doing, George. I'm so glad you like to lick and suck my boobies and I'm glad I have them now, to give us both so much fun. But now my pussy needs you more." After a final lick on both her nipples I complied, and got up to kneel near the foot of the bed. Jill got to her hands and knees just in front of me, and piled pillows under herself.

She unbuttoned and unzipped her skirt and I reached underneath to caress her lovely hips and ass, really enjoying the feel of her soft flesh under the silk panties that I had known would be there. After pleasuring my hands on her smooth skin, I pulled the skirt down to her knees and gazed at her beautiful, creamy ass through the sheer panties. Although there are some, such as her parents, who would insist that Jill is a man, her ass is more womanly than that of many of my lady friends, and has no resemblance at all to what I sometimes see in the men's locker room at the gym.

I have no real basis of comparison but I am quite sure it feels nothing at all like one of those either. After pulling the skirt off and tossing it aside, I fondled her some more through the silk before reaching my fingers into the waistband of the panties and pulling them down partway. She giggled as I kissed each bare buttock before pulling the panties around her beautiful ass cheeks and down to her knees. One at a time, she lifted her knees so I could pull her panties all the way off and toss them near her skirt. Completely naked, Jill wiggled provocatively at me. Before getting into serious love-making, I decided to take off the rest of my clothing. My hands were busy but I was able to plant more gentle kisses on her delightful ass. She seemed even sexier there than on previous visits and I believe the hormone treatments were helping those bodily contours also.

Once I had tossed aside my underwear and my pants, after taking the Aquaglide and a condom from the pocket, I resumed caressing the lovely body in front of me. As I put my thumbs into the cleft of her ass cheeks with my hands on her buttocks, Jill, knowing what I was about to start doing, arched her back and lowered her face to the mattress to better present herself to me for licking, followed by fucking. "I washed my pussy just before you got here so it's all ready for you," she assured me, reaching her hands back to spread her cheeks to show me how clean and ready she was, and to encourage me to start licking her.

It didn't take much urging because I love to lick Jill's ass before fucking her as much as I love to eat a pussy before fucking it. Knowing how scrupulous she is about personal cleanliness, I had no qualms about what I was doing. At the top of her cleft, next to the base of her spine, I started by swirling my tongue around. In this area, I used a fair amount of pressure but, as I slowly licked down one side of the cleft, I stroked more gently. Very slowly, reveling in the way the soft skin felt on my tongue, I licked Jill's beautiful and extremely lickable ass.

When my tongue reached the place where I could feel the puckering start, I licked around it, down to the lower end of her cleft and started back up. Once again, I skipped the puckered area, wanting to save the best for last, and licked my way up to where I had started. "I love that, George," Jill told me. "I love the way you eat my pussy."

She also knew the best was yet to come, and I started licking down the center of her ass cleft. Jill was cooing again, squirming in delight in front of me, and thrusting her ass against my face. She expressed herself even louder when my tongue reached her adorable pink rosebud and I licked with short strokes of my tongue, caressing where we both liked it the most. Although I spent a long time there, giving pleasure to both her and me, we knew it was still not the best for either of us.

Jill's hands continued holding her ass so my hands were free to take my condom from the foil pack and roll it on my cock. Once it was enclosed in latex, I removed my tongue from where I had been licking and replaced it with the nozzle of the Aquaglide. When she felt it there, Jill was well aware of what it was. "I hope you do as good a job fucking my pussy as you did eating it," she told me.

That was certainly my intention and, after squirting the lubricant inside her ass and spreading it there and all around the puckered hole, I covered my cock too. With both of us ready and Jill holding her cheeks open, I reached into her ass and spread the sides open. Holding her open with the fingers of one hand and guiding myself with the other, I placed the tip right at the entrance. Jill murmured happily as the head of my cock made penetration and repeated her little sounds of pleasure as I started slowly thrusting into her, a little more of my shaft wedging in with every stroke, until my entire cock was embedded in her.

Using the towel that was there for that purpose, I wiped off my hands and placed them on Jill's hips. Slowly, I backed my cock most of the way out of her and, equally slowly, I fucked it all the way back into her ass. From the intense pleasure she was feeling, she moaned and fucked back to meet me. Again, I drew the shaft of my cock out of her ass, leaving just the head inside and thrust it all the way back into her and Jill moaned and fucked back to meet me.

Again and again, I plunged my cock in and out of Jill's tight but well-lubricated ass. Every time it surged into her, I marveled at how wonderful it felt, the way she opened up for me and the way her ass squeezed my shaft, sending pleasurable thrills throughout my body. With every stroke I heard Jill moan, expressing how wonderful it was for her too. She has described to me the feeling of my cock fucking her ass, telling me about waves of ecstasy sweeping through her, growing in volume with every thrust into her pussy until, when she reaches her climax, they have become a tidal wave. That's how it usually is for her but this time, although she was immensely enjoying our fucking, there was something missing.

"Can you play with my clit?" she asked me. "I can't cum without it."

For a second, I was taken aback until I realized she meant what I had been thinking of as her cock. Just as what I call her ass, she speaks of as her pussy, the organ I had always called her cock is, to Jill, her clit. She is on very solid grounds biologically, because a cock and a clit are closely related and, just as most men can't cum without stimulation of their cocks, most women need something happening to their clits for them to climax. Her cock is so small it's more like a large clit anyhow.

Jill's hands were not available because they were still holding her ass open, helping me achieve maximum penetration. Besides, I consider it to be not right for one of my lady friends to have to fondle herself to reach a climax when I am there. I was in the full mounted position, fucking down into Jill, and I couldn't reach her clit from that position. "We'll have to lie on our sides," I told her.

Slowly and carefully, with my cock at maximum penetration, we tipped over onto our left sides. After plunging my cock in and out of her ass a few times, I found there were advantages to our new position. It was much more intimate, with my front pressed tightly against her back and my left arm around her waist. With my right hand, I could stroke her lovely hips or belly or breasts. After briefly caressing her nipples with my fingertips, I moved my hand down to do the same for what I had started thinking of as her clit.

For a few minutes we continued fucking and, as I approached my climax, I could tell there was still something not right with Jill. When I fondle a clit to help bring a woman to her climax, I don't actually touch her there because it is too sensitive for my fingers, so I massage all around, providing indirect stimulation, and this is enough. That kind of caress wouldn't work for Jill, though, and the angle was too awkward for me to stroke her clit as if I were masturbating a cock. My fingers were too clumsy anyhow. Usually, Mary or somebody sucks Jill's clit with their mouth to bring her to orgasm but there was nobody else there that day.

I have several principles that I always follow and the main one is that I will do anything within reason to give a lady friend maximum enjoyment. What I would have to do was very clear to me. "Wait until I cum, Jill," I told her. "And then I'll get you off."

Since I was on the verge of cumming anyhow, and I no longer had any need to hold back and wait for Jill, I put my hands on the fronts of her hips and drove my cock in and out of her ass for a few more strokes. I felt a sudden rush of pleasure and the muscles in my ass clenched as I climaxed and ejaculated into my condom. With a few more long, deep strokes I finished cumming. Usually, I would wait until my cock softened and slipped out of her but I wanted to take care of Jill's needs while her pleasure from fucking was at its height.

Carefully, I pulled my cock, still almost hard, out of Jill's ass and rolled onto my back. "Get into the 69 position," I told her.

She saw what I had in mind and hurried to comply, her legs straddling my face and my cock near her mouth. My hands were inside her ass cheeks and, as I have done with dozens of other women, I drew Jill's clit into my mouth and sucked on it, while my tongue caressed the sides. It was longer and harder than what I was used to but, to me, it was a clit anyhow.

While my lips and tongue were caressing her and she was fucking down into my face, Jill removed and discarded the condom from my cock, which had softened by then, and took it into her mouth to suck the cum out. She doesn't always get a chance to do that but she enjoys it when she can. "Ahhhhhhh!" she sighed, and I felt the muscles in her ass clench as she climaxed, spurting a viscous fluid into my mouth.

I knew what it was, of course, and I continued to suck on her clit until I knew she was through cumming. By that time, Jill had sucked and licked all the semen from my cock and she got off my stomach to lie down beside me. For a long time we lay cuddling and kissing, the way we like to do, and I thought about what we had just done. The position we had been in when we finished fucking had worked quite well and we would probably want to use it again. I also decided that, in the future, I would prefer to make love when Mary or somebody else was there but if it should happen again that there was nobody else, the two of us could make love, just Jill and me together.

Thank you for reading this story. I hope you enjoyed it as much as I enjoyed writing it. Whatever your opinion, please express it by voting. Like all the writers here, I also like to get feedback, either an email to me or a personal comment left at the end of the story. I promise to answer any email or PC that includes an email address or a handle.

Boxlicker101
Boxlicker101
3,138 Followers
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3 Comments
AnonymousAnonymousover 7 years ago
Thanks for practicing safe sex

Thanks for including the bit about the condom most stories don't and safe sex is important

FRSWRITERFRSWRITERalmost 14 years ago
cool

tranny sex rocks

AnonymousAnonymousover 18 years ago
Good story!

Liked your story; next time try frontal, or missionary position, or even cowgirl. That way her clit is available for you to manipulate. Makes for a wonderful mutual cum!

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