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Waking Up with Brooke – By TheGuyInBlack (edited)
Tim was very proud to be a student at Penn State, but tonight he was in a sour mood. As a student, he was a die-hard Nittany Lions football fan, which made this moment particularly frustrating. The team had just lost a heartbreaker to Ohio State in double overtime after an incredible 4th quarter comeback by PSU. Sure, Ohio State was clearly the better team, but that doesn’t mean he had to be happy about it.
As he was walking out of the stadium, he and his friends decided the best course of action was to go back to his dorm, and get well and truly drunk. This was a rare occurrence for Tim, as he didn’t much like how drinking made him feel, but he wanted to forget the last three hours of his life.
They got back to Tim’s dorm and cracked open the two bottles of whiskey that his roommate bought for the weekend. Despite his dislike for becoming belligerent, Tim wasn’t one to turn down a glass of bourbon.
When he woke up, the first thing he noticed was his pounding headache and the bright sun shining through his window. It had to be past noon already. He must have blacked out because he remembered nothing of the previous night. The second thing he noticed was that his roommate and all his friends were gone, presumably at the out to get something to eat to help get rid of their hangovers.
But the third thing he noticed was by far the most surprising: the girl he vaguely recognized sleeping beside him. He wondered if he was dreaming. He wondered where he recognized this girl from and what they had done the night before. At least it explained why his roommate was nowhere to be found as they agreed to find somewhere else to sleep when the other brought a girl home. Tim honestly didn’t think he’d ever have to kick his roommate out, as he was chronically single and a virgin. Well, depending on what happened last night at least.
With a small yawn the girl beside him woke up. Now he recognized her. Her name was Brooke, and they’d recently been matched on Tinder. Tim felt very self-conscious as he noticed they were both naked. He wondered what happened and hoped he didn’t embarrass himself last night.
“Morning,” Brooke said with a smile.
She looked very attractive to him. The girl next door type if Tim had to describe her. She was on the shorter side, probably 5’3″, maybe 5’4″ with shoulder length brown hair and eyes to match. He looked at her smallish but very perky breasts with small, hard nipples. He noticed her feet poking out of the bottom of his blanket. Tim was a big foot fetishist, and the sight of hers made his cock stir, which didn’t go unnoticed.
“I see your little guy’s up again,” she said with a giggle, causing him to blush. “I’ll take that as a compliment.”
“Yeah,” he said and laughed nervously. “Hey, I’m really sorry, but I was super drunk last night and don’t remember what happened. Did we?”
“We fooled around, but didn’t go all the way,” she said.
Tim felt so relieved.
“You said something about wanting to be sober for your first time, so all we did was oral.”
Oral, he thought. I can live with that. She’s gorgeous, but I’m glad my drunk self was able to show restraint. “How did I do?” He asked, genuinely curious.
“Well, you were hesitant at first, but I could tell you wanted to try it from how hard it made your little cock. You needed a little practice at first, but by the end of the night you were doing it like a pro.”
Her comment about his size made him blush again, as he wasn’t very well endowed at only four-inches. Then it registered what Brooke had just said.
He asked, “Hesitant? Why would I be hesitant to eat your pussy?”
This prompted yet another one of her giggles. “Wow, you must have really been out of it, huh?” She rolled her eyes jokingly. “This is why you were hesitant.”
She pulled back his blanket to reveal something that made Tim’s heart leap to his throat. Resting between her thighs instead of a pussy was soft, thick, circumcised cock. Already bigger than him fully hard. Tim’s eyes nearly bulged out of his head. “Oh my God! You have a COCK… And it’s bigger than mine!”
He had to admit that it made his boner throb. “That’s right,” Brooke said with a wink. “And you couldn’t stop telling me how horny it made you last night. What do you think now?”
This made him think. Of course he has jerked off to tranny porn before, but he never dreamed he’d be naked sharing a bed with one. “I don’t know, can I have a minute to process this?”
She put her hand on his thigh and kissed him on the cheek. “Sure, sweetie, you take all the time you need.”
With that she got out of bed and started to put on her clothes. He had to admit that the sight of her cock was mesmerising. He wondered what it tasted like, and how big it was when it was hard. “Text me, when you figure it out,” she said with a smile, and just like that, she was out the door.
Tim laid back down, his head spinning. What the hell am I going to do about this, he wondered? There was no doubt that he was incredibly attracted to Brooke, and she seemed to like him as well. How could someone so beautiful have been born a guy, he thought to himself? He had never thought of himself as gay, but as he thought about Brooke and her perky little tits, cute ass, and beautiful cock, Tim decided that he had to at least give it another try with her when he was sober.
It took a couple of hours to work up the courage, but he finally got up the nerve to text her. She was glad he decided to go further, as she really liked him, and his tiny cock. She also noticed his lingering gaze on her toes, which was perfect as she loved to have her feet kissed and licked and sucked. She decided she would have to paint her toenails before they next met.
Tim didn’t much care for the hook-up culture of his generation, so he decided to try to see if there was any way this could turn into something real. He asked her out to dinner, and a smile broke out across his face when she accepted.
They met at a small restaurant just off campus, and Brooke greeted him with a smile and a kiss on the cheek. “I’m glad you texted me,” she said after they sat.
“Me too,” Tim said, and seeing how beautiful she was in person, he meant it.
They talked while they ate, mostly about her and her transition from guy to girl. Brooke knew that he needed to feel comfortable if things were going to go anywhere, so she was happy to help him understand. She had always known she was a girl, even though she was born in a boy’s body. Her family, luckily, was very forward thinking and were very accepting of her. They started her on hormone treatments before she started puberty, which is why she was able to develop to be so feminine. But for some reason she had just enough testosterone to keep her cock developing normally. And, as she said, the best part is her breasts eventually grew to a point where she didn’t need implants. She considered having surgery to remove her girl-cock, but once she heard of the possibility of losing sensation, she decided against it almost immediately.
Tim was getting more and more comfortable with the thought of what she had between her legs as the night went on. They were getting along great, and they both thought there was definitely a chance of this becoming something real. At one point she put her foot, now with freshly painted toenails, against his crotch, feeling his cock hard through his jeans. He jumped at first, but gave a little laugh when Brooke gave him a wink. They both knew tonight was the night, without even needing to discuss it.
“Your place, or mine?” Tim asked as they began to walk back.
“I think your roommate deserves to sleep in his own bed tonight,” she said with a smile. “Besides, my roommate’s home visiting her family until tomorrow night.”
Tim liked the sound of that. “Sounds great,” Tim said with a smile.
He sent a text to his roommate letting him know he wouldn’t be home tonight, which Tim was sure made his roommate happy, as that meant his girlfriend was free to come over.
When they got back to Brooke’s room, they started kissing like they needed each other to breathe, hard and passionately. Tim loved the way her lips tasted, he could tell that she was wearing cherry lip gloss, his favourite flavour.
This went on for about twenty minutes when Tim broke the kiss, pulled Brooke’s shirt over her head and took off her bra, letting her perky tits free. Without hesitation, he clamped his mouth over one of her nipples, making her gasp with pleasure. “Oh, you’re a bad boy, aren’t you?” She asked.
He popped his mouth off of her breast. “Yeah, are you going to punish me?”
“Later,” She promised. “But first, I’m going to reward you.”
She took off his jeans and pulled down his boxers, letting his already hard cock free. “Oh, I see someone’s ready to go.”
She made eye contact as she took all four inches of it in her mouth as easily as sucking on a lollipop. She worked on his shaft for all of five minutes when out of nowhere he felt his balls tighten and he shot cum right into her mouth.
“Someone’s a little over-excited,” she said with a grin. “I guess it’s OK though, considering how hard your cock still is.”
Tim looked down and noticed that she was right. Despite having just had a mind-blowing orgasm, his cock was staying rock hard. “Besides, you can make it up to me by worshipping my feet,” she urged.
Tim looked at her feet and noticed that her already amazing feet were made even sexier by the fresh coat of red nail polish Brooke had put on her toes that afternoon. The sight made his already hard cock throb. “Well,” she said, “Get to it.”
He happily obeyed, bringing her right foot to his face, kissing each toe very gently, making her sigh as she closed her eyes. He started sucking on her toes like they were each a tiny cock, warming up for what was sure to follow sometime tonight. He liked the bottom of her foot, making her giggle as she was apparently ticklish. He went on worshipping her foot for a good fifteen minutes before switching feet and giving it the same treatment.
Tim looked up after he had finished with her other foot and noticed that her cock was already rock hard inside her panties. “What are those still doing on?” He asked.
She responded by pulling them down and off, and putting them in his face. This turned him on to no end, the smell of her cock and precum driving him wild. He tried to place the scent, the best way he could describe it would be a feminine musk, if there were such a thing.
His eyes then focused on the lovely girl-cock in front of him, and the tight ball-sack hanging below it. It was the most beautiful thing he’d ever seen, and he told her just that. “Well then, why don’t you kiss it?” She dared.
He put his face just inches from the throbbing shaft, opened his mouth, and closed it around the head of her cock, tasting the precum and making her shiver. “Oh, God, yes.” He heard her moan. He took this as a sign of encouragement and started working on her shaft with his lips and tongue. He bobbed up and down on her thick seven-inches, amazed at how long and thick she was, he could only get a little past halfway down her length.
This went on for about ten minutes, and his jaw was starting to ache when he finally heard her say “Watch out, I’m gonna cum!”
He took her out of his mouth and made eye contact as she started to cum, shooting hot, thick ropes of spunk all over his face and into his waiting mouth. “Mm… You look so hot with your face covered in cum,” she said lustfully.
The feeling of the hot jizz on his face made him feel incredibly slutty, and he loved it. She started stroking his cock, which had gone limp while he was sucking her, and said, “Baby, I want you to fuck my asshole.”
This immediately made his cock spring to life, he couldn’t believe he was going to lose his virginity to this gorgeous tranny.
She took him into her mouth again to coat his now throbbing cock with saliva to use as lube. As she was sucking him, he coated two fingers with his own saliva to finger her tight ass to lube it up as well. She laid down on her back, with her legs spread to give Tim easy access to her hole. “I’m waiting, big boy,” she teased.
He looked at her as his heart started racing. He had been dreaming of his first time for years, and here it was! He had never imagined it being with a tranny, but seeing her cock now limp hanging from her body, he couldn’t imagine losing it to anyone but this beautiful girl in front of him.
He got on top of her and kissed her deeply as his cock slowly went into her well lubed hole. She moaned as he began to penetrate her, easily fitting his small cock balls deep into her asshole. He stayed still for a few moments to get used to the feeling. He could feel her muscles squeezing the cock that was invading her ass. After a few moments, he started to move slowly at first, then faster and faster. He was fucking her at a steady pace when she started moaning at the pleasure of being fucked in the ass. “That’s right, baby, give me your cock. I don’t want to be able to walk tomorrow because of how hard you fuck me,” Brooke moaned.
This turned him on so much, hearing this cute girl talking so dirty. He started fucking her even faster, making her moan even louder. He noticed her cock was beginning to harden again so he took it in his hand and started stroking in time with his thrusts. She was almost screaming at this point, and by the amount of precum leaking from her cock, he could tell she would cum soon.
To make her cum even faster, Tim used his other hand to massage her balls, which made her shiver. Eventually this became too much for her, as she screamed with pleasure, arched her back, and came for the second time of the night.
Tim loved pleasuring her, but knew that he was close to cumming as well. So he flipped her onto all fours and started fucking her doggy style. This made her ass muscles squeeze his cock even harder, and he had to fight to keep himself from cumming right there. But he was able to hold off for another five minutes or so, Brooke moaning the entire time. Finally, Tim said, “I’m about to cum, baby, what do you want me to do?”
Between her moans, Brooke said, “Keep fucking me! I want to feel you shoot your hot load deep inside of me!”
This was the last straw for Tim, as he felt his balls tighten up and he shot his second load of the night into this beautiful tranny. They both collapsed on Brooke’s bed, fully exhausted. She looked at him and said “So, how was your first time?”
Tim looked at her, kissed her deeply, and said, “It was the most incredible thing that’s ever happened to me.” She smiled happily at him. “I’ve never felt this way about any girl I’ve ever met,” Tim said. “How would you feel about being my girlfriend?”
“I’d love to,” Brooke said. With an evil grin she said, “On one condition.”
“We get to take turns being the girlfriend.”
Tim was confused for a second, then noticed her cock was sticking straight up, hard as a rock again. He remembered what she said about punishing him for cumming too soon earlier. He could tell she wanted to return the favour he just gave her. The thought of being impaled on her big cock made his cock stir.
“Seems only fair,” he said with a grin, knowing the two of them would be sharing many nights to come.