T-girl's Double Date

"I tell you, this is the greatest fuck ever," Mike Shoemaker told his best friend, Pete Olson as they stood outside an unfamiliar tavern one Friday night.

"Is she really a woman? Are you sure she's not just a guy who looks like a girl and likes to dress like one."

"Okay, she used to be a boy but that was a mistake of nature. She changed her sex and she's 100% woman now. She likes to call herself a t-girl."

"Does she wear falsies? Does she have a dick?"

"No, she's got real tits. And they're big and really real, not some kind of phony plastic junk. Okay, she does have a dick too but don't worry about that. She'll wank herself while she's sucking us off and getting fucked. Look, would I give you a bum steer? I met her in this bar last Saturday and fucked her. In the ass 'cause she ain't got a pussy but it was the greatest, smooth like silk and nice and tight. Anyhow, we made a date for tonight but she wanted me to bring another guy with me and that's you. At least it is if you want it to be."

"Oh, okay. Sounds like it might be fun and I don't have nothin' else to do."

Mike led Pete went into the bar and looked around until he spotted the woman whom they had been discussing, right where she had said she would be - in a booth in the back where it was dark. After his eyes had adjusted to the dim light, Pete saw a large blonde woman with long hair and big breasts and a pretty face. She was wearing a pink sweater that was very nicely filled out.

"Hi, Jennifer. This is my buddy Pete. Pete, this beautiful woman is Jennifer. Now, tell me I didn't mislead you."

They shook hands. Both of the men were a bit hesitant to kiss a mouth that had entertained any number of cocks but Jennifer didn't seem to mind the omission. Mike went to the bar to get a round of draft beer because he knew the others both preferred that, as did he. While he was gone, Pete sat down beside Jennifer and seemed to be unable to take his eyes away from the pretty blonde's big chest.

She didn't seem to mind. "Do you like what you see?" He nodded and she said "They're all real and they're all me. Do you want a feel?" After making him that offer, she thrust out her breasts and they became even more enticing.

Pete reached out, took hold of one lovely mound in either hand and squeezed lightly. She was not wearing a bra and Jennifer's breasts were big and soft and full and, generally speaking, one of the nicest handfuls he had ever gotten. Any doubts about her true gender disappeared and he started becoming impatient and wanting to go somewhere with her to do what they were intending to do. He had to admit, he had not been given a bum steer.

Mike returned with the beers and noticed how much closer the other two were sitting on the bench seat. He smiled, glad to see everything was going well and set the beer on the Formica table top before sitting across from the other two. They all drank from their glasses. All three of the people sitting in the booth were there for sex and they all knew it but there was still a certain reticence toward bringing up the subject. Finally, Jennifer said what everybody had been thinking even before the men had arrived.

"Do you guys want to come over to my place? I live right down the street and we can walk or you can drive."

Pete had driven that evening so he led the others to his car and they all got in, with Jennifer in the front seat. She directed the driver to a small apartment house just a block away and they parked in front. It was late enough there was no concern about overtime parking and the building was on a well-lighted main street. Jennifer unlocked the door and led the way up the stairs, which they enjoyed because they were able to watch her ass sway in her short red skirt. She appreciated their attraction to her and looked back over her shoulder and smiled at them.

"You'll get a lot better view in a few minutes," the t-girl promised.

After locking the door to her apartment, they went straight to her bedroom. None of them had changed their mind; they still all knew what they were there for and nobody wanted to waste any time being coy about it. Jennifer stood by her bed, took hold of the bottom hem of her sweater, pulled it up and all the way off and hung it on a wooden chair, shaking her hair back into place as she did. When she faced the men again, she was holding her breasts in her hands to show them off.

"This is what I got after six years of hormone therapy," she told them. "Do you guys think they're worth it?"

Both men agreed absolutely that they were, because Jennifer's breasts were large and firm and jutted nicely. Although she was supporting the lovely pair with her hands, there was really no need to do so because her voluptuous bosom stood out with no support needed. When she lowered her hands and took a step toward them, the succulent globes swayed and bounced alluringly and either of the men reached out, took hold of one of the beauties and bent over to start licking the small pink nipples.

"That feels really great, you guys, but let me lie down and it'll feel a lot better to all of us."

Mike and Pete had nothing but good things to say about that idea so they moved aside and their sexy companion lay on her back and slipped a pillow under her head. They removed their shoes and socks joined her and continued their worship of her luscious breasts. After a few minutes, Jennifer's body was squirming on the bed and she was moaning softly from the pleasure they were giving her.

Pete raised his head briefly and looked in the direction of where a woman's pussy would usually be and was a bit surprised to see her skirt tented in a way he had often experienced himself. He realized Jennifer, although possessed of a delightful pair of breasts and a shapely, feminine ass, would display her sexual arousal the same as a man would. He called the fact to the attention of his friend whose mouth was sucking on their companion's breast.

Jennifer was aware of her condition too. "I'm ready, you guys. Let me turn over on my stomach."

They both moved aside and, once Jennifer was lying face down with a pillow under her waist, she looked at them again and chided their slowness in getting prepared. "You know, you can't do much with your pants on."

They quickly removed their shirts and pants and underwear and stood there waiting to see what their sexy blonde partner wanted to do first. She looked at the two naked men, both of whom were tall and dark-haired and good-looking and were sporting erections but she saw one of them was slightly longer and thicker than the other and that was the man Jennifer invited to join her first.

"Mike, there's some rubbers and a bottle of lube on the dresser. Bring them here and I think you know what to do then. Don't worry, Pete. My mouth will be all yours in a few minutes."

He was rather surprised to see the condoms were the type with small pleasure bumps but, after selecting a packet and holding the squeeze bottle of lubricant, Mike returned to the bed and knelt beside Jennifer. She was still wearing her skirt but he found the button and small zipper on the side, pulled it off and left it on the corner of the bed. That left only silky pink panties and Mike hooked his fingers in the waistband and pulled the last garment around Jennifer's luscious cheeks, down her thighs and all the way off.

The sexy woman's ass had looked great walking up the stairs but it looked even better when she lay naked on the bed, like a pair of lovely white hillocks. She reached back and spread the succulent pair and Mike looked between them at the dark pink rosebud he would be fucking momentarily. He removed the cap from the bottle, placed the tip just within the pink hole and squeezed in a generous dollop, to be rewarded with a sigh of pleasure from Jennifer.

Before continuing with her preparation, Mike knew he had to get himself ready. He rolled one of the condoms onto his stiff cock, squirted a few drops of the lube onto his left hand and used it to coat his erection. He was ready so, using the thumb and forefinger of that same hand to pry apart the sides of Jennifer's rosebud, he carefully inserted the middle finger of his other hand as far as his knuckles and used it to evenly spread the lube. By the time he was done with the preparations, the hot t-girl's ass was squirming on the bed and Mike was just as eager as she to replace his finger with his cock and plunge it all the way inside the welcoming hole.

Jennifer was already having a great time and she knew the best part hadn't started yet. Having her ass prepared had been pleasant but she knew the man's finger was just a small precursor to the fucking she was about to get. She'd had a lot of fun with Mike the previous Saturday but one man wasn't really enough to satisfy her. She was reasonably sure, however, that night's combination of the two men in her bed would be enough.

She reached back and spread her ass cheeks. "Okay, Mike. Really give it to me," she said. "You know how I like it."

Mike did know, and it was the way he most liked to fuck. While Jennifer kept her succulent cheeks apart, he held her rosebud open and pressed the end of his cock against the small hole being created. With everything ready, he gave a firm push and the head wedged into her. The t-girl moaned in pleasure as she felt herself being forced open just the way she liked. Mike paused no more than a few seconds before thrusting forward again, this time plowing almost an inch of his hard shaft into the tight hole that felt so good.

What he was doing felt fantastic to Jennifer, with intense joy rippling out from where her ass was being stretched and the adjacent channel expanded. Best of all, with one more firm stroke, Mike's cock, with the array of pleasure bumps on the condom he was wearing, started to rake her prostate gland, sending an even better kind of pleasure coursing through her body. She moaned in bliss from the combination and his cock continued burrowing its way, in small increments, into her tight ass until it was completely imbedded in her.

Pete had not been forgotten and, after the dick plunging in and out of her ass and working its magic, Jennifer knew it was time for him to join in the fun. Holding his cock in his hand, he eagerly advanced on his knees; Jennifer raised her face, rested her weight on her forearms and opened her mouth. Pete knew better than to jam his cock between the waiting lips but he did slide it partway in and let the eager t-girl move her face forward to meet him.

For the first few strokes of her mouth, Jennifer took the welcome visitor only in as far as the back of her throat. Her lips applied the perfect amount of pressure and her tongue curled around the hard cylinder but she wanted more. She did not want to open her mouth to give instructions but she wanted to give deep throat to the man whose cock felt so good. Jennifer reached out, placed her hands on his ass and started to pull him closer to her face. He knew what she wanted and moved in right next to her so she could take the length of his cock into her mouth and down her throat.

Mike had been able to plow his entire shaft into the her ass until his pubic hair was tickling the insides of her cheeks. Jennifer's body was squirming under him, making the fucking some of the best he had ever gotten. Good as it was, he knew how to make it better. He had been kneeling between her thighs and pulling back on Jennifer's hips as he plunged his cock into her but he changed that. Instead, he sprawled atop of her back and slid back and forth, pulling on her shoulders to make the deepest penetration possible. She didn't say anything, having her mouth too full to talk but she did start fucking back to meet his strokes.

Jennifer was having a great time, just as she had anticipated. Ever since her hormone treatments began and her name had been changed from Jeffrey, she had loved taking on two sex partners at a time. She was especially partial to having them take turns and alternate between her ass and her mouth while she used her hand to masturbate but she had not reached that level of arousal yet. Until she did, she would concentrate on the joy of having both her pleasure centers filled with hard dicks.

She was letting Mike set the pace. Every time his cock surged into Jennifer's ass, she fucked back to meet him and withdrew her mouth most of the way from the hard shaft passing between her lips. When Mike partially withdrew for another slow, deep stroke, she moved her face forward to envelop Pete's cock all the way into her mouth and down her throat until she was tickling her lips and nose on his pubic hair.

They continued like that with no need for talking, fucking and sucking with all three of them relishing every second. The lube in Jennifer's ass was working perfectly and Mike felt no friction at all, only her tightness squeezing his cock and the muscles massaging him with every stroke. He also felt his climax steadily mounting and knew he would be coming within a few minutes.

Jennifer didn't know about that but she did know Pete was on the verge of his climax. His body was writhing in bliss and she could feel his cock throbbing inside her mouth so she tightened her lips and stopped giving deep throat. She wanted his semen to land on her tongue so she would be able to fully relish the flavor and texture. Pete knew he was close to coming too, of course and he wondered what to do about it. Every girl or woman who had ever sucked him off before that night had removed her lips from around his cock so he wouldn't come into her mouth but Jennifer had shown no such squeamishness. When she tightened her lips and sucked faster, it was obvious she wanted a mouthful of his juices.

"Oh, yeah!" he grunted as he climaxed, a load of cum erupting right onto the place Jennifer wanted it.

It was delicious, thick and meaty tasting and slightly salty. She didn't stop her sucking but continued until Pete had ejaculated twice more, both gobs of his semen landing on her tongue and pleasing her taste buds. She continued to suck on the hard shaft until she was sure he was through with his climax, then took the cock but of her mouth so she could thoroughly enjoy the three loads of cum she had caught. Jennifer swirled the viscous liquid in her mouth, relishing the texture and taste before letting it slip down her throat.

She was still holding Pete's cock lightly in her hand and she licked off every drop that was clinging to it before swallowing that cum too. As she licked, she was happy to note the shaft was still almost hard enough for him to fuck her ass with it. Even after her attentions toward him had ended, Pete lay on his side, well aware of the semi-erect state of his cock and hoping the same thing the sexy t-girl was.

After finishing the blow job, Jennifer started to concentrate on her own erection and the one that was driving in and out of her ass. Until swallowing the ration of semen Pete had given her, she had been moving back and forth, rubbing her cock against the sheet but she needed more than that and would get it from her own hand.

"Let me get up on my knees now, Mike," she requested of her second partner.

He knew what that would be for because she had done the same thing the previous weekend and he knew it would give him more fun than he had already been getting. While keeping his cock buried all the way in Jennifer's ass, he placed his hands on her hips and pulled up while she raised her upper body by pushing up with her hands and arms. When they reached the desired position, she was on her knees and his cock was still all the way inside her ass and he was kneeling behind her. He left his hands on her hips, both affectionately and to pull against for greater leverage. After a few seconds while Jennifer adjusted her legs, they resumed fucking in the new position.

Mike drew his cock back until only the head was still contained by Jennifer's sphincter, paused and started plunging it back into her eager ass. She fucked back to meet it and, before the next stroke, she leaned forward, bowing her back and presenting him with a better target. When the thick cock started burrowing back into her and massaging her prostate, Jennifer's arms were wrapped around the pillow she had been lying on and she pushed back from the bed, meeting the surging cock halfway. They moaned from the exquisite pleasure and Mike started pulling his dick back again.

She adjusted her arms and legs slightly so all the weight of her upper body was supported on her left forearm and reached up with her other hand to take hold of her own cock. It was fully erect and swinging to and fro with hers and Mike's movements. Once again, she let him set the pace as she stroked herself in the rhythm of his long, slow thrusts into her ass. This gave her a new source of pleasure and the squeals and moans of her joy were louder and even more heartfelt than they had been a few minutes earlier.

Mike was having a fantastic time too. Before entering the bar, he had described Jennifer as the best fuck ever and he had not changed his mind. Her ass was tighter than any pussy he had ever experienced and the lubricant continued to work perfectly, so he still felt no friction as he plowed his cock in and out. The sensations he felt were the tightness, the well-trained muscles in her ass and the adjacent channel as they massaged his shaft and the strange feeling of his balls as they swung against hers while they fucked.

After a few more minutes of the combined sexual thrills, Jennifer knew her orgasm, which had been mounting steadily within her body, was on the verge of exploding. "Fuck me faster, Mike," she turned her head to tell her partner. "I'm almost ready to come."

He was very glad to hear that and more than ready to do what she wanted. His own climax was also close to erupting so he started pounding his cock faster into the t-girl's ass. She responded by matching his pace, both fucking back to meet him and in stroking her cock.

As Jennifer's orgasm became imminent, her legs were thrusting down into the mattress and her body was thrashing in front of Mike. His hands remained on his partner's hips, no longer just out of affection and for leverage but also to keep her from falling over, because the hot blonde had lost control of almost all her muscles. However, neither of them would let that possibility keep them from fucking as hard and fast as they could.

They weren't having a race but, if they had been, Jennifer would have won. The combination of exquisite delights coursing through her body from her ass and her prostate and her hand overwhelmed her body and her climax started to overwhelm her. She cried out in ecstasy and a thick stream of semen shot out from her cock to land on the sheet. Her hand continued pumping and a smaller gush joined the first, to be followed by a third. Her body became suddenly weak and she collapsed forward to land on her belly in the sticky mess. She didn't care because she expected to shower and remake the bed anyhow, after their sexual fun was over for the night.

The first part of it was about to end for Mike. As Jennifer sprawled forward, he stayed with her and, once she was prone on the bed, he gripped her shoulders again and resumed ramming his cock in and out of her ass until he uttered a loud sigh of delight and blasted a big gob of cum into his condom. As his t-girl partner had done, he didn't stop then but continued to cram his cock into her ass and pull it back out until he had also ejaculated three times. Mike knew he was done, at least for a while and he remained on top of Jennifer's back with his cock buried all the way in her ass.

Jennifer had no intention of calling the carnal fun over for the night but she had to rest a few minutes before continuing the escapade. While lying on her belly, she saw how the cock that been so good in her mouth was almost ready for more action. A few strokes between her lips and it would be ready for Pete to encase it in a condom and bury it in her ass. The shaft that was inside her already had softened enough for Mike to pull it out of her and she could take it into her mouth and suck him hard and continue until he had fed her a good mouthful of his cum.