Jill & David & Me: A Threesome

For background on this story, see “I Call on Jill and Mary”.

Of all my lady friends, one of the most beautiful faces belongs to Jill, with long, blonde hair, blue eyes, regular features and an unblemished peaches-and-cream complexion. I enjoy kissing her all over her lovely face but, unfortunately, her breasts have been almost non-existent until very recently and she has a cock. Jill is a transsexual and, since she is a woman in every way but anatomically, I consider her to be a woman and I make love with her almost as I do with any other woman. She has no pussy for me to eat, of course, but I love to lick her gorgeous ass before we fuck. Jill always keeps herself scrupulously clean, especially what she calls “her pussy”, and even more especially when she anticipates a sexual encounter.

Jill called me last week to tell me she needed my company and that Mary, her closest friend and roommate, was out of town visiting relatives. This could have been a problem because Jill cannot cum just from having her ass licked or from fucking so usually, while Jill and I fuck, Mary sucks her off. This is something of a compromise because, although Mary really likes sucking off her friend, Jill would prefer to have her cock in a man’s mouth. I contacted David, a bi-sexual friend, so I could arrange the time and the date for the three of us to get together at Jill’s apartment. Once I knew what day he would be off and his wife would be working, allowing him to join us, I contacted Jill to set up the date. She was looking forward to meeting David and I knew that Jill would please both of his sexual sides.

When Jill let us in the door, she and I hugged and kissed the way we usually do, and as I do with all my lady friends when we haven’t seen each other for a while. Our kisses quickly went from affectionate to passionate as we opened our mouths to let our tongues get re-acquainted also. When I introduced Jill and David, they shook hands, but after that, she opened her arms and they embraced and kissed the same way as Jill and I had. I was glad to see that they seemed quite compatible because I expected all of us to really enjoy ourselves.

Even though Jill’s roommate was not there, we intended to use her bed. This was at Mary’s suggestion because Jill’s bed is too small for a threesome, and Mary, a really sweet person, wanted us to have fun, even if she wasn’t going to be able to join us. The three of us stood by the side of the bed with Jill in the middle. We both had our arms around her and she turned and kissed first me, while I fondled her lovely ass, then David while he played with her cock. “This is going to be a ball,” Jill said, and neither David nor I disagreed.

Usually Jill wears the most sexy, feminine things she can find and when we have made love in the past, she has been naked except for a padded bra under a silky negligee. On this day, though, she wanted me to undress her completely. “I’ve been taking hormone treatments,” she told me, “My titties are growing and I want you to lick them and play with them.” I untied the ribbon the ribbon on Jill’s negligee and she turned around so I could remove it and unhook her bra.

When she turned back to face me, I could see her breasts were beginning to swell. I was glad for her and wanted to encourage her so I cupped my hands under them and bent down to lick her nipples which, although small, were erect and felt good on my tongue. The soft skin around her areolas and nipples felt good to my hands and lips too. “Very nice,” I told her. “You’ve always been beautiful and your ass and pussy are really sexy and now you’re getting to be sexy all over.” Jill smiled, very happy to hear that.

David was more interested in her cock so, while I was caressing Jill’s breasts, he was removing her mini-skirt. She was getting aroused from my tongue on her nipples and the anticipation of what would be happening soon and Jill’s cock was bulging her sheer silk panties. He removed those next and Jill was naked between us. David gently fondled her balls and knelt to take her stiff cock in his mouth. “This is already a lot of fun,” she said. “But why don’t you guys get naked too, and join me?”

While we were taking her suggestion and undressing, Jill sat on the bed to wait for us. When I was naked, I resumed licking Jill’s breasts but after a few minutes, she stopped me, saying “That really feels good, George, and my new titties and I appreciate it, but what I really need is to have you eat my pussy.”

Jill got onto her hands and knees and pulled a pillow underneath herself so she could rest her face on it. With the side of her head on the pillow, she looked back and smiled prettily. “I really love what you do for me, George,” she said as she reached back and spread her ass cheeks so I could lick where we both wanted my tongue to be. Jill has a really beautiful ass, smooth and curvy with skin as soft and creamy as the skin on her face. Happily, I started licking at the top of her ass cleft and slowly continued down the inside of one cheek. Jill’s ass is as soft and sexy as that of any of my lady friends and I really enjoy licking her there, just as much as I would enjoy licking the ass or pussy of any other woman. I ignored what was sticking out in front of Jill, considering it to be an unkind quirk of nature that this lovely woman should have been born with a cock.

David didn’t ignore her cock, though. While I was licking her ass, He wanted to slide underneath her and place a pillow under his head so he could suck her off. That was what Jill wanted too, and she raised her face off the bed to let him get into position. With his hands high on her hips, he moved his face up and down, stroking her cock with his mouth. While David was sucking on her, she licked and fondled his cock until it was stiff then, supporting her upper body on one forearm and, caressing his balls with the other hand, she sucked him slowly in and out of her mouth.

While she was 69ing with David, I held Jill’s ass cheeks open and finished licking down the inside of one cheek and around the puckered area, avoiding her lovely pink rosebud until later. I am one of those persons who likes to save the best part for last, in this case, the best for both me and Jill. My tongue traveled slowly up the other ass cheek, again skirting the puckered area until I reached the point where I had started. Jill’s pussy is always a delight for my tongue, smooth and soft and absolutely clean.

Using my thumbs, I spread Jill’s ass cheeks and looked at where my tongue was heading, her sweet pink rosebud, nestled in its beautiful surroundings. Eagerly, but still taking my time, I started licking my way down towards my adorable goal. Jill knew where I was heading, of course, and she stopped sucking David’s cock to concentrate on her own impending climax. Between what I was doing with her ass and what David was doing with her cock, she knew she would cum soon.

When I reached the puckered area, I licked the top part and Jill sighed happily. “I love that, George; I love what your tongue is doing for my pussy. I love what your mouth is doing too, David.” She loved David’s mouth so much she started to fuck down into it, which is something he usually doesn’t like. In the case of Jill, however, her cock is small enough that he could easily accommodate her so he rested his head on the pillow and tightened his lips so she could fuck down into his mouth.

Jill continued to love what my tongue was doing. I licked, using considerable pressure, all the puckered area, circling her hole and, as my tongue caressed all the sensitive ridges, Jill moaned in pleasure and fucked David’s mouth harder. After completing the circuit, caressing all the tiny ridges with my tongue, I reached in with my fingers and gently opened her precious rosebud.

At first, I licked up and down, reveling in the feeling as my tongue dipped into her ass with every stroke. Jill moaned from the pleasure we were both giving her and told us again how much she loved what we were doing. She even reached back to help me open her pussy so I could actually make penetration and when she felt the tip of my tongue squirming into her, she gasped with pleasure and started cumming. I had difficulty remaining where I wanted to be because, as Jill drove her cock between David’s lips, her buttocks clenched at every spurt of semen she pumped into him. Using his tongue to press her cock against the roof of his mouth, David milked out all her cum and when her cock softened he rolled it around with his tongue.

Jill is considerably younger than either David or I and we expected her to cum twice, both times giving David a mouthful of her semen. Although her cock was soft, it would stiffen again after she and I started fucking so she left it in David’s mouth. One of his favorite things is feeling a cock get hard in his mouth anyhow, so nobody had any objections. Much as I had enjoyed licking Jill, especially her rosebud, I knew both of us would have even more fun when my cock entered her ass and we started fucking. I went to get my condom, put it on and applied the Aquaglide to my cock. While I was gone, Jill resumed sucking David’s cock, bobbing her head up and down and taking it all the way into her pretty mouth. David is an expert on sucking cocks and he really liked what she was doing to his.

Jill’s mouth stroked David’s cock while I was applying the lubricant to her but she stopped and reached her hands back to spread her ass cheeks when her pussy was ready for fucking. While she spread herself, I opened her sphincter with the fingers of one hand and my other hand guided my cock into the slick, tight hole where we both wanted it. Jill murmured happily as the tip of my cock penetrated her ass, and again when my first stroke imbedded an inch of my shaft in her.

“I love that, George. I love the way your cock feels in my pussy.”

She loved it even more as I slowly pumped my cock in and out of her, always making sure no loose skin was caught. Jill gasped from pleasure at every stroke as I wedged deeper into her ass, spreading her sphincter the way she likes it and massaging her prostate. “My God, George, your cock feels good,” she told me when it was all the way in her. “Now give my pussy a nice, slow fucking.”

The penetration of her ass had caused Jill’s cock to become completely stiff and David was again sucking on it, with his hands back on her hips. He slowly moved his face up and down, taking her cock between his lips and all the way to his throat, and I knew his tongue was caressing Jill’s cock as she plunged it into his mouth. My hands caressed Jill’s delightful ass because caressing her soft, smooth womanliness is so much fun, but then I put my hands on the front of her hips and started backing my cock out for the first stroke. When my cock surged forward, she fucked her pussy back to meet me. After a few more slow, deep strokes, when our rhythm was established, Jill bent forward and resumed sucking David’s cock.

Silently, except for my occasional moan of pleasure, I fucked Jill’s gorgeous ass, especially enjoying the way she thrust back to meet me. At every stroke, my cock penetrated her all the way, and I felt my balls gently bouncing against hers. Neither David nor Jill is particularly hung so both of them were able to take the other’s cock all the way into their mouths and caress it with their tongues. They were truly enjoying themselves, both sucking each other off and having their own cocks sucked. Both David and Jill like to use their tongues to caress a shaft that enters their mouths and increase the pleasure they get and give. They were silent too, except for an occasional murmur of pleasure and the erotic slurping noises as they stroked their mouths on each other’s stiff cocks.

David was ready to cum first and he took Jill’s cock out of his mouth to tell her. Jill appreciated knowing that and she tightened her lips on his shaft and sucked it faster in and out of her mouth. Like most people David preferred to concentrate on his own climax, and after he had cum, he would finish sucking off Jill. Until then, her cock lay across his face where David could nuzzle it with his lips. I continued slowly plunging my cock all the way into Jill’s ass and I would continue the same pace until she had cum into David’s mouth.

Jill bent over David, rapidly bobbing her head up and down while he thrust his cock into her mouth. “Yes! Yes!” he blurted out as his body spasmed and I knew he had ejaculated, giving Jill the mouthful of cum she wanted. David remained motionless but Jill continued taking his cock into her mouth, squeezing it with her lips and milking out everything he had for her. My cock and Jill’s pussy continued pleasuring each other.

When Jill had drained everything, she removed his cock from her mouth. “Delicious,” she said, while licking under the ridge. “I really love two dicks at once.” After she had finished licking off his cum, David’s tongue snaked out and pulled Jill’s stiff cock back into his mouth and he resumed sucking her off.

Jill was already moaning from the pleasure my cock was giving to her pussy and the mouthful of cum from David and what he was doing to her cock brought her close to her climax. “Fuck me hard, George, I’m almost ready to cum,” she announced. Once Jill said that, I started stroking my cock faster into her ass, still thrusting it all the way in so my balls bumped against hers. David lay passively, letting her fuck into his mouth, but his tongue remained just as active, stroking Jill’s shaft as she thrust it between his lips. Her cock is small enough that David really enjoyed being fucked in the mouth like that.

Tacitly, we established a rhythm. As I plowed my cock into her pussy, Jill fucked back to meet me, both of us moaning from the pleasure we were getting from each other, while we enjoyed equally the pleasure we were giving. As I drew back to prepare for the next stroke, Jill drove her cock into David’s welcoming mouth, moaning from the pleasure she was getting from his lips and tongue, while he murmured his delight at the way her cock felt thrusting against the back of his throat. All three of us delighted in pleasuring ourselves and each other until Jill’s cock started throbbing and she announced she was ready to cum.

As Jill had earlier, David tightened his lips to get the mouthful of delicious semen he expected to get from Jill. I continued pounding my cock into her ass, stimulating her prostate so she would ejaculate more strongly into David’s mouth, the way I know she likes to do. David likes it that way too and I knew his tongue was positioned to catch her cum so he could savor it before swallowing.

When Jill ejaculated, I knew because I could hear her sigh happily and I could feel her ass clenching my cock with every spurt she pumped into David’s mouth. He milked her cock the way she had milked his because he knew how good her semen would taste from when she had cum earlier, and he didn’t want to waste any. For as long as I was fucking Jill’s ass, David kept her cock in his mouth, rolling it around with his tongue even after it had softened.

Jill was relaxed from her second climax, and ready to fall forward to land with her face in David’s crotch, but I kept my hands on her hips, continuing to ram my cock into her ass until I also ejaculated, filling my condom. After that, we both fell slowly forward, with David moving his head out of the way but letting Jill’s cheek rest against his cock. All three of us lay in a happy and satisfied pile until it was time for David and me to leave.

Before we left, David and Jill did a lot of kissing, partly from affection and partly to lick the semen off each other’s lips. “I had a really great time, you guys,” she said. I hope we can get together again, either one of you or both of you together.” David and I both felt the same way, and we all wanted to get together, and soon.

Thank you for reading this story. I hope you liked it as much as I liked writing it. I have fun writing stories like this one but I have a lot more fun if I know people are reading and enjoying them. I really appreciate feedback, either a Public Comment added to the end of the story or an email to me. Any kind of comment, either positive or negative is welcome and I am always open to suggestions about new story ideas. I always respond to any feedback I receive.