Loading...When Jill was born the medical staff looked at the baby’s genitals and told the parents “You have a baby boy.” The baby was named Jack, after his uncle and spent the next several years as a boy. Jack never got involved in sports with other boys, partly because of his small stature and partly because he felt more at home playing with girls.
He enjoyed wearing his older sister’s clothing whenever he could. The sister, who was empathetic beyond her years, permitted, even encouraged this, and sometimes they went out together. Jill was the name used then, and with her long blonde hair, fair skin and padded bra, Jill was a very cute girl.
Jill’s parents saw no humor in the situation. They celebrated her eighteenth birthday by kicking her out of their house. Jill expected this and had already arranged to move in with Mary, the older sister of one of her youthful playmates. She never again referred to herself with male pronouns and never again called herself Jack. Her friends, including myself, completely agree with her. Jill’s wardrobe consists strictly of feminine garments, especially including bikini panties and matching padded bras. When she confided in me regarding her background I told her, with total sincerity, that I was 100% on her side and that she was one of the cutest girls I knew. She kissed me fully on the lips and I happily kissed her back. Genitalia do not equal gender.
Jill and Mary still share an apartment and the last time I went there, we all kissed each other hello and headed for the queen-sized bed in Mary’s room. I unzipped Jill’s and Mary’s dresses and unhooked Mary’s bra. Jill prefers to wear her bra and a negligee while making love. Mary stepped out of her dress, wearing just panties, and lay on the bed. She is short and rather chubby with an pleasant, but not very attractive face. Because of her big heart and sweet nature, however, I consider Mary to be one of the most beautiful people I know. I removed my clothing and knelt, naked on the bed beside her. I lightly squeezed one soft titty and started licking the nipple. My other hand was caressing her belly and hip and thigh. Mary pulled off her panties and my hand was caressing her soft skin.
Jill came up behind me with a basin of soap and warm water and washed off my ass. She took my cock briefly in her mouth, and sucked it for a few strokes, her very talented tongue caressing it and her lips pumping it. I knew she was just saying hello to a dear friend because we both had other plans for my cock. Jill began licking my balls then, and took one into her mouth and caressed it with her tongue. She treated its mate to the same gentle mouthing and then licked my crotch, heading up. I knew her tongue would be in my ass in a matter of minutes.
Meanwhile, Mary’s soft mammaries were the object of my tongue and my mouth. I clamped my lips around one and applied gentle suction while licking her nipple. I ran my tongue slowly around the areola and against the sides of the nipple. Mary was breathing hard from the attentions I was paying to her sweet titty and I was enjoying it also. I moved my attentions to its twin just as Jill started licking my ass. Her clever tongue gave me pleasantly erotic feelings as it laved the cleft of my ass, and I knew it would be even better when she made penetration.
Mary’s sweet pleasure globe felt even better in my mouth than Jill’s tongue felt on my ass, delightful as that was. Mary was enjoying it too, and moaning in pleasure. Her hips were writhing on the bed and I could smell her fragrant juices as they lubricated her pussy. The time had come for me to go the rest of the way down on Mary. I licked my way down, starting with the channel between her twin beauties, and stopping when I reached her soft pubic hair.
To properly eat Mary’s pussy, I was going to have to kneel between her legs. This meant that Mary had to move to near the head of the bed with a pillow under her ass. Her legs were over my shoulders and my arms were wrapped around her thighs. I moved my knees in closer to elevate my hips and give Jill better access. She reacted by spreading my asscheeks and stretching my hole open with her thumbs. Just as my tongue entered Mary’s sweet love hole, the tip of Jill’s clever tongue entered my ass. I squirmed my tongue deeper into Mary’s pussy as Jill squirmed her tongue deeper into my ass, until both our tongues were in as deeply as they would go. I slowly removed my tongue from the lovely place it had found and began nibbling, with my lips only, on Mary’s pussy lips. I kissed the outer lips gently as a butterfly, while my tongue traced the seam between her inner and outer labia.
Jill removed her tongue from my ass to catch her breath. She is a woman in every respect except her genitals. She had become sexually aroused by sucking and licking on me, and her cock was hard. When Mary saw this she wanted Jill to sit on her chest so she could suck Jill’s cock. None of us had any problem with this so I leaned back away from Mary’s pussy and Jill straddled Mary’s chest. Jill has no great interest in sex with a woman but Mary likes to suck her cock and Jill is happy to accommodate her friend. She leaned forward with her cock at Mary’s lips. Mary pulled the hard cock into her mouth and leaned back with it and Jill proceeded to fuck her roommate in the mouth.
As I said, Jill is a woman in every respect but her genitals and this is especially so with her ass. It is soft and smooth and delightfully curvaceous. In her silky black negligee, Jill has one of the most exquisitely beautiful female asses I have ever seen, even with the balls that were now bumping gently against Mary’s chin. The skin on Jill’s ass is soft and unblemished and creamy-smooth and I thought lustfully that soon I would have my cock buried all the way in it, and Jill’s beautiful ass would be fucking back to meet me. Jill’s cock would stay hard in Mary’s mouth but Jill wouldn’t cum until she and I started fucking. Then she would probably cum at least twice, but that would happen later. For now I was relishing eating Mary’s pussy.
And a very nice pussy it was, too, with its juices trickling in her love hole. I licked up all those juices, being sure I didn’t miss any and again started licking my way up a pair of Mary’s pussy lips. I planted the same nibbling butterfly kisses on her outer pussy lip while my tongue was gently probing the seam between her inner and outer lips. Mary was breathing hard, partly because of what I was doing to her lovely pussy and partly because of Jill fucking her in the mouth. I reached the end of one pair of pussylips and started on the other pair. Mary wouldn’t cum until I got busy on her clit and that wouldn’t happen for a while. She was enjoying what my mouth was doing to her pussy and I was enjoying what her pussy was doing to my mouth.
What her pussy was doing was humping up into my mouth as I nibbled and probed my way along her second pair of pussy lips. While I was concentrating on her labia, I stopped every few minutes to lick up Mary’s delicious juices. After I got to the end of the second pair of pussy lips, I started probing with my tongue into the inside of Mary’s inner lips. She is very sensitive there and started humping harder into my face. Her thighs rotated slightly out and her pussy was totally presented to my mouth. Mary was ready to cum but I wanted to delay a few minutes longer. I continued with my tongue on her inner pussy lips until I reached her clit, then I clamped my lips around that sweet love button and started to flick it with my tongue.
Mary didn’t want to bite down on Jill’s cock while she was cumming so she pushed her roommate away. “Yes!! Yes!! Ahhhhhh” she called out as she started to cum. I continued to suck on Mary’s clit and lick it with my tongue, partly because I liked it so much and partly because she had her thighs clamped around my head. Mary was humping her pussy even harder into my face, almost lifting her ass off the bed, in time with my tongue caressing her clit. She had wrapped her arms around Jill’s hips and was mashing her friend’s pubic area against her face. Mary continued to cum for several minutes, and then climaxed with one last big thrust of her pussy against my mouth and a squeeze of Jill’s ass. Then she sank back into the mattress and relaxed, and I licked all the delicious cum juices from her pussy.
The time had come for Jill to be the center of our attentions. As Mary rested I went and got another basin of warm water. Jill was on her hands and knees and I carefully washed her ass. Although she has a cock and balls I have never thought of Jill as being anything but a cute young woman with a really beautiful ass and I enjoy pleasuring that beautiful ass the same as if she were biologically a woman. Licking and then fucking her ass is the same to me as licking and fucking a pussy. Jill knew this and was anxious to get my tongue and especially my cock into her ass. Her cock had softened after being removed from Mary’s mouth but had become harder while I was washing her ass, and now Mary lay on her back under Jill and took that semi-hard cock in her mouth.
I spread Jill’s asscheeks and started licking at the top of her cleft. Jill’s skin is soft and smooth and felt almost as good on my tongue as my tongue felt on her ass. Jill murmured with pleasure as my tongue licked its way down her cleft. Mary appreciated it also because Jill’s cock was getting stiffer in her mouth. I licked Jill’s adorable rosebud with broad strokes of my tongue. I made no attempt to insert my tongue because my cock would do a much better job. I licked all the way down to her crotch and then back up. Jill’s rosebud seemed to be winking at me in anticipation of what would come next. Jill’s cock was fully hard by now and was going in and out of Mary’s mouth. I rolled on my condom and applied the KY Jelly to my cock and to Jill’s ass.
After the lubricant was all applied Jill reached back and spread her asscheeks. With my fingers I opened her sphincter and pushed the head of my cock in. Jill cooed with pleasure and told me what a nice cock I have. She is tight, but I knew that in a few minutes my cock would be all the way in Jill’s beautiful ass, massaging her prostate. I gave another push and another inch of cock entered her ass, causing Jill to coo again with pleasure, louder this time. I continued with the short strokes, getting more and more of my cock into its delightful haven. Jill continued to express her pleasure as my cock spread her sphincter more with every stroke. Her expressions of pleasure urged me onward until my entire cock was buried in Jill’s tight, beautiful ass. Jill’s cock was as hard as my own now, giving Mary the mouthful of meat she desired.
I waited a few seconds and then pulled my cock most of the way out. I applied more KY Jelly and slowly thrust my cock all the way back in. Jill trilled in ecstasy and pushed her ass back to meet my forward thrust. She reached back to spread her asscheeks to get the maximum penetration. I continued deep, slow strokes, my cock going all the way into Jill’s lovely ass. She coordinated her motions with me, thrusting her ass back, providing the maximum pleasure for both of us. Mary contentedly lay on her back, letting Jill’s cock fuck her in the mouth. Nobody said anything intelligible. Jill was cooing and sighing at the pleasure Mary and I were giving her. I was grunting as my cock penetrated Jill’s beautiful ass. Mary’s mouth was too full for her to say anything.
Then Jill sped up the pace. She started fucking her cock faster into Mary’s mouth and her ass faster back to meet the strokes of my cock. “I’m going to cum”, she trilled. I matched her pace, being sure my cock continued to achieve the maximum penetration. With a cry of delight, Jill pumped a big load of cum into Mary’s mouth. Mary swallowed the cum and milked Jill’s cock to get it all. While Jill’s cock was being drained of cum, I waited, with my cock totally buried in her ass.
After a minute or so, I slowly pulled my cock almost out of Jill’s lovely ass, so just the tip was still in, then I slowly plowed it back in again, all the way to the hilt. “Your cock is so wonderful,” she cooed. “I’m getting hard again.” Again I slowly pulled my cock almost all the way out and slowly pushed it all the way back into Jill’s beautiful ass. She cooed her pleasure again and reached back to spread her asscheeks so my entire cock would penetrate her eager ass. I continued the deep, slow strokes and Jill resumed thrusting her ass back to meet my cock and fucking her cock into Mary’s mouth. We continued the slow but immensely pleasurable activity for a long time. Jill was cooing and sighing in pleasure and she told me again how wonderful my cock felt in her ass. I told Jill how much I was enjoying fucking her beautiful ass, and how I wanted this to go on forever. Mary’s mouth would have been too full for her to say anything, but she took Jill’s cock out briefly to express her pleasure.
Nothing lasts forever. Although I was fucking Jill’s tight ass slowly, I could feel my climax approaching. I told the women I was getting ready to cum. “Me too”, said Jill. On the next stroke back I applied more KY Jelly to my cock, then began thrusts that were faster but went just as deep into Jill’s delightful ass. She matched my speed with her own, pushing her ass against my pubic area and her cock into Mary’s mouth. I increased the pace and shortened my strokes, still plowing my cock all the way into Jill’s incredible ass, but not withdrawing as far. I could feel my balls slapping against Jill’s as I continued with the short, quick, deep strokes. She uttered an unintelligible but unmistakable ecstatic cry and I could feel her ass tightening around my cock. I knew she was cumming and pumping another load of her cum into Mary’s welcoming mouth. I told Jill I was cumming and after just two more strokes into her tightened ass, I shot my load of cum into my condom.
Jill and I backed away from Mary. My cock was softening rapidly but was still deep in Jill’s ass. She reached back and gently removed it and peeled off the condom. I lay on my back and Jill took my soft cock into her mouth and sucked out all the leftover cum. She didn’t expect me to get hard again but she likes the taste of my cum and she likes to roll my cock around in her mouth. Jill is very fond of my cock. She especially likes it in her ass but she also likes the feel of it in her mouth, whether it is hard or soft. After swallowing two loads of Jill’s cum, Mary was hot for some more action so she came over and sat on my face. I licked the bounty of delicious pussy juices out of her love hole and clamped my lips on her clit and started to suck on it, while probing that adorable love button with my tongue. Mary was so aroused that it didn’t take much sucking and probing before she started cumming. “Ahhhhhh” she called out while humping her pussy down into my face. She climaxed with a jerk of her thighs around my head then fell forward to hug Jill and lick some of my cum out of her friend’s mouth. We all knew the love-making was over for the day but we were already looking forward to the next time I would call on Jill and Mary.