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Matt had been gay his whole life. He knew from a very young age that he was not interested in women. Thankfully, he lived in an accepting state where same sex marriage was legalized long before others. His parents were pretty accepting and open of his lifestyle, so he knew no shame in being who he was.
He started dating Josh in high school and never stopped. They were the perfect couple. They even sometimes finished each other’s sentences. They were together for eight years before they moved into a house together while going to college nearby.
Bills quickly overwhelmed them so they interviewed quite a few roommates as potential candidates to move in with them to help them out with paying off some of their debt that had accumulated. They just needed a few hundred more dollars a month to get by and a roommate would give them that, so it made sense for them to get one as the best option. It was that or move back in with one of their families and they really liked having their own space so that would be a last resort option.
Most of the candidates seemed alright but there was one that really stood out. Her name was Anna. When they interviewed her, she seemed perfect for them. She was a very open minded individual. She was tall, slim, and had a nice, curvy body with big, firm breasts. For a woman she was extremely good looking with long brunette hair and big brown doe eyes.
She was very straight-forward about her needs and wants for a roommate and she seemed like the perfect fit. She liked things clean, she was very organized, willing to help with chores. She explained that she had a lot of boyfriends and liked to have sex a lot. She wanted to make it clear if she moved in, she would have all shapes and sizes of men around during her down time and that she would be drinking. Which was fine because Matt and Josh liked liquor just like the next person.
Matt thought it was strange when she also said that she might slip up and flirt with both Josh and Matt, because they were very attractive men. She went on to explain the flirting would be totally harmless, as she knew they were a couple and gay men so nothing could ever happen between the three of them. No harm, no foul, right? A little flirting never hurt anyone so neither of them were offended by it.
Out of all the potential roommates, Anna seemed the best option. So, after much deliberation, she moved in that weekend. Matt and Josh were just excited to have extra money that they could use to pay off their credit card debt and other various bills that had seemed to pile up as the months went on.
After Anna moved in things changed drastically for Matt. Matt was an attractive guy with jet black hair and stunning emerald green eyes. He got hit on by both men and women and never really took offense when women assumed that he was a straight man. Not many people think outside the box these days. He was not a very feminine man by any means, and he could understand that he could come off as straight if someone did not get to know him well.
Anna was not at all shy about telling Matt how attractive he was. It made him uneasy at first. Although she was a good-looking woman, he was faithful to Josh and had never ever once in his life seen himself with a woman. He had never been sexually attracted to them whatsoever. But it seemed like Anna would just flirt with him any chance she could get. She had warned that she was a flirt, but she seemed to touch him any chance she got on top of the flirting.
It was subtle at first. She would touch his arm or rub his shoulder. She would sit close him on the couch when they were watching tv to the point where their arms were pressed together, and he could feel the warmth coming from her body. It seemed a little passive aggressive to him but when he brought it up to Josh, his boyfriend just laughed it off saying it was all fun and games and completely harmless. Anna knew they were gay so it could not be serious, right?
So, Matt dropped it and let it go. The flirting continued. The touching continued. Over time, Matt got used to it, and warmed up to Anna more. She was funny and smart and had a great personality. She was very open about her sexuality, which was something Matt really admired. Despite being openly gay, he was the opposite of Anna, and had never really flirted with anyone aside from Josh, and he didn’t often let on that he was gay unless he became really close to someone and wanted them to become an actual friend.
After a couple weeks during a school break, Anna, true to her word, started having various men over every night. Matt swore she timed it so that it only happened when he was home alone with her. Josh was studying to get a degree in information technology to become a desktop support technician, so he was interning at a nearby software company and worked long hours despite going to school. They had talked about Matt getting a job, but with Anna around, they did not need him to. So, when he was not at school during the day, he was home in the house with Anna when she wasn’t working herself.
One night she came home with another guy and barely acknowledged Matt before she went to her room with what looked like Brad from the college football team. He thought nothing of it, knowing they were probably just going to be getting drunk and having sex.
Matt continued to watch TV for about twenty more minutes before he got up to go to the bathroom. To get there he had to walk by Anna’s room. He swore she had done it intentionally, but the door was cracked open just enough for a voyeur to be able to peek in and see what was going on in the room.
Matt was the target voyeur of course. He heard moaning coming from inside the bedroom and to this day he did not know why, but he decided to peer in to watch the erotic sex he knew was happening inside.
Brad and Anna were naked on her bed. It was strange for Matt to see a woman naked, he tried to avoid it when possible. But for some reason, seeing the two having sex on the bed was really turning him on. Anna was riding Brad’s condom covered cock, her big tits bouncing rapidly as she bucked and writhed on Brad’s steely pole.
Matt could not deny that Anna had a beautiful body. She had full round breasts and a nice pert ass. And she clearly knew how to service a cock. Brad’s grunts and groans were becoming louder the more Anna rode him like she would a bucking Bronco.
Matt had a huge tent in his jeans. He began rubbing it as he watched the seductive scene before him. He carefully slid down his zipper and pulled out his turgid rod. He began to masturbate furiously, knowing he had to cum quick before he got caught watching. There was something about Anna’s moans and the way she was begging for Brad’s big cock to fill her up that turned him on like no other.
She was so loud he was sure that the neighbors must be hearing them and feeling a little jealous. Hell, even Matt was jealous in this moment that it was not him on the bed. Wait, what? No. That was wrong! He had no idea why he that would ever even cross his mind. He reasoned it to the fact that he was just incredibly horny and needing release in that moment.
Matt could tell that Brad was getting close, as was Anna. Both their moans and groans were rising in crescendo. They all came at the same time. Brad into the condom, Anna on Brad’s thick meaty cock, and Matt all over his t-shirt and face.
He hurried to his room to change his shirt and then quickly into the bathroom to take a shower. The feelings he felt from there on out were confusing. He loved Josh, he knew that, but seeing Anna on the bed writhing over Brad had been so erotic to him that he could not help but wonder what it would feel like to be Brad. He quickly scolded himself after, knowing full well that he was just horny and confused. It was perfectly normal to feel aroused while watching people have sex, right? It wasn’t any different than watching porn, he reasoned.
After that night, life went on like normal. Anna continued to flirt with Matt whatever chance she got. When Josh was not home, she would kiss his cheek when they were hanging out making dinner together or watching TV. She made every excuse to touch him in any way. Sometimes when they were on the couch together, she would put her hand on Matt’s knee and smile a seductive smile as her fingers caressed him over the fabric of his sweats, giving him goosebumps.
Matt just let her do it. He let Anna touch him in any way she wanted. Josh seemed to think it was totally innocent, so he convinced himself it was too. But then she seemed to grow bolder as time went on. Like when they were cooking dinner together and sharing wine and they were both getting a little tipsy. They were in proximity of each other in the small rectangle kitchen and making spaghetti with a homemade sauce.
One way or another, Matt somehow ended up getting sauce on his nose as he was tasting it. When Anna saw it, she laughed.
“You’ve got a little sauce on your nose there, handsome,” she said, with that charming grin of hers on her face.
When Matt reached up to wipe it off with a napkin, she swatted his hand away and then leaned up and licked the sauce off his nose with a laugh. He laughed too. And then she kissed him on the lips.
The cheek was one thing, the lips was entirely different. By now Matt was very used to being close to her and having her pet him and touch him. But kissing? That was a different story, right?
The kiss happened so quickly that he was so stunned he did not say anything. What could he say? She kissed his cheek all the time. She slapped his butt and sometimes squeezed it. She constantly touched his arm, rubbed his shoulders and gave him little massages, put her hands on his chest under his shirt, pet his legs near his knees and thighs. By now he was very used to her fondling him in any way she possibly could and they both passed it off as inoffensive friendly gestures of affection. They had known each other awhile now and he considered her a good friend to both him and Josh. He had no reason to suspect that she had ulterior motives in mind.
So, he rationed that that is all it was. Friendly touching between two good friends. His lips tingled from where she had kissed them, but he was quick to shrug it off and move on with life. He did not think of Anna in that way. Even after seeing her and Brad, he had moved on from that and he did not feel attraction to her at all anymore and he had not witnessed any of her other sex-escapades after that one time.
So, he decided to find no harm in the kiss. It was not like she shoved her tongue in his mouth! It was a peck and nothing more. Could it even really be qualified as a kiss?
After that night, the kisses became more frequent. And always when Josh was not around. Maybe that should have tipped Matt off that there was a possibility that Anna was trying to seduce him. The woman was a maneater. She came home so many different nights with so many different men that Matt and Josh had lost count. But he was oblivious to that being a possibility. Each time they kissed, he now thought nothing of it. He got used to it just like he got used to all her other handsy and verbal advances. Kissing her on the lips became normal to him.
So, it should not have come as a surprise when another night when they were making a surprise dinner for Josh when he got home from work later while getting drunk that she kissed him again. He was stirring the sauce when she came behind him and put her hand on the small of his back. He thought nothing of it and smiled at her when she held a strawberry to his lips to eat. He chewed it and some of the juice dribbled onto his chin.
Anna licked the juice off his skin and then kissed him. He returned her kiss but this time it was longer than normal. Matt was feeling pretty buzzed at this point, so he hardly noticed. Anna stepped into him and he could smell her intoxicating vanilla perfume. Her lips were so soft. It was different than kissing a man. That is all he was thinking. That and it felt nice.
They kissed for a long moment before Anna pulled back. “I thought you only kissed men,” she teased, with a flirtatious wink.
Matt blushed. “I do. I did. Until I met you.”
“Do you like it when we kiss?” Anna asked, and her tone was casual, as if they were just having a normal conversation.
“Sure. It’s like kissing a good friend. It’s not sexual.”
“Right. Because you’re gay,” she countered.
“Right.” He laughed. Was this getting awkward? Why were they having this conversation?
“So, I guess you won’t mind if I do this then,” Anna said, leaning in and kissing him again.
He kissed her back. It was long and drawn out. He could feel Anna’s fingers tangling into his hair as their lips met repeatedly. It was a series of soft pecks that lasted for a couple seconds at first. One after the other. They must have shared about ten kisses back to back.
On the last kiss, Anna tugged on Matt’s lower lip playfully. When Matt let out a groan of protest, her tongue entered his mouth. They started to kiss deeply, and their arms went around each other. Anna sucked on Matt’s tongue before it left her mouth, and it was a long time later before their lips were pried away from each other.
“I like kissing you, Matt. And it means nothing because your gay right?”
Matt shrugged. “Sure. I mean, I guess.” But was he so sure? That was the question. Hadn’t they just been full on making out?
“Well, good,” Anna said, and he liked the feel of her fingers stroking the hair on the nape of his neck.
She kissed him again and he returned it. Before he knew it, they were making out again. They could not seem to get enough of each other’s lips. And Matt did not think anything of it. They had agreed their kisses were friendly. And it was not going to go any further. What was the harm in it? There was none.
After that night, as soon as Josh left for work, Anna would pull Matt in for hungry kisses. They would kiss all the time and make out passionately. Matt would just let her kiss him whenever she wanted. He would return them and kiss her deeply. He loved the taste and feel of her lips. Sometimes cherry, sometimes strawberry, sometimes vanilla. All flavors that Anna knew Matt liked from getting to know him over the months they had lived together. And her lips were so soft like pillows. Josh’s mouth was rough, and his lips always seemed chapped. It felt very different kissing Anna. Eventually Matt really grew to love it and crave her friendly kisses.
Making out with Anna became routine. He never once got a hard on when they were doing it. To him it was normal behavior between friends. He was not at all rationalizing that Josh would see it as cheating if he happened to come home early and see them doing it. Because he did not think of Anna in a sexual way. He was gay and that was that. He never planned on doing anything more with Anna then kissing and harmless touching.
Anna invited Matt to go clubbing with her before Josh left for work. Josh thought it would be a great idea and encouraged Matt to go so he could get out of the house. Matt usually only left to go to the grocery store or occasionally go shopping for new clothes or appliances to better their home. Josh teased him about it all the time, calling him a hermit. So, naturally, he agreed to go to hopefully lose his hermit status. Why not? It was just going to be Anna and a few of her girlfriends. It could not be that bad.
They arrived at the club and Matt nearly rolled his eyes when Anna squealed when she saw her friends Hannah, Brittani, Emily, and Jessica. She rushed over to them and gave them all hugs and then came back to Matt and intertwined their arms.
“Guys, you finally get to meet my awesome roommate Matt. He is gay and taken so do not dare think about hitting on him! Only I can do that,” she joked, and her friends laughed uproariously at that. “If you see us kissing or touching, it’s normal. We’re all over each other when his boyfriend isn’t around, aren’t we, Matt?”
Matt shrugged and he felt himself getting uncomfortable. “Yeah, I guess,” he said, deciding to just agree with Anna. He knew it was true, but she was making it sound like it was sexual when he knew it was not. But he did not want to be in a sour mood and ruin their night out, so he let it go. Besides, it made all the girls giggle and they seemed to think that Anna was joking anyway, so they said nothing more about it.
They all entered the club and found seats. Anna paid for the first round of shots of tequila. The club was not far from the house so thankfully Anna and Matt had just walked the distance. That meant they did not have to worry about one of them being sober for a drive home. If anything, they would just call a cab.
Matt knew there was no way in hell he was going to get through the night with all these girls sober. He was on his third shot when Anna suggested they all dance together. By then Matt had a good buzz going on but he was not near close to being drunk yet.
The dance floor was packed, but he and the girls soon found their place and began to dance. The girls began to touch Matt in various ways. He really did not care about it because he did not feel any anything sexual toward them. He knew he was attractive so of course they were going to put their hands all over him. They were thrilled that he did not seem to care.
“Oh my God, Anna, you are so lucky to have such a hot gay roommate!” Hannah exclaimed. “He doesn’t even care when we touch him.”
Anna laughed. “Of course, he doesn’t. He doesn’t feel anything sexual toward us, right Matt?” Anna asked, an innocent look on her adorable face.
“That’s right,” Matt returned, with a smile. Again, he was feeling slightly uncomfortable, but he just let it slide. He was having a good time despite the weirdness that was happening between him and all the girls.
Anna came over to him and wrapped her arms around him and kissed him. The girls really got a kick out of it and began to hoot and holler. Matt was feeling tipsy, so he just returned each of Anna’s deep kisses, ignoring her friend’s responses to it. Before he knew it, they were giving the girls quite the show as they made out on the dance floor.
Anna pulled back and they all kept dancing. Soon enough they went back to their table and did three more shots. That is when Matt started to feel drunk. The girls insisted they dance more before they go home. They found a few guys to join in the fun and Anna stuck with Matt and another guy named Adam.
It was no surprise to Matt when Anna her arms around his neck and they began to make out again. Matt sucked on her tongue and rolled his around hers as they kissed, and she danced all up on him. When she broke the kiss, she pulled Adam closer and began to make out with him too. Matt watched them do it and then soon was kissing Anna again. When their kisses finally broke, Anna raised her eyebrow toward Adam, who cupped Matt’s face and began to kiss him deeply. Kissing Adam felt good. Real good. And again, he compared it to kissing Anna. Her lips were so much softer, and she tasted so much sweeter, but damn Adam was a great kisser.
Shortly after seeing the two men kiss, Anna decided she wanted to take Adam home with them to have a private party with more drinks. Matt agreed that was fine, so they all walked home together. It was late when they arrived home, but Josh was still at work when they got in the door and would be for a few more hours at the very least. Sometimes his job required him to work late or stay over his scheduled shift. Since Josh was so dedicated to becoming employee of the month, he always agreed to work the extra hours, as it meant more money for them to spend when his paycheck came.
As soon as they all settled on the couch, the three of them started drinking again. Why not right? Anna got out the tequila and poured them shots. She sat between Matt and Adam on the couch when she returned with the drinks and started making out with Adam as Matt nursed his shot and tried to focus. He was feeling extremely buzzed and horny from Adam’s earlier kisses.
Before he knew it, Anna was kissing him, and he was returning her heated kisses. When their lips parted, Adam was right there waiting to kiss Matt. They kissed hungrily and all the kissing between Anna and Adam was starting to arouse him. He could feel Adam’s fingers in his hair as they kissed, and their tongues were dueling and dancing before they parted ways. Matt’s drunk mind did not want the kisses with Adam to end. He was hot and hunky and Matt was not rational enough from the alcohol right now to think about the fact that he could end up cheating on Josh if things continued beyond kissing.
“God, that sight will never get old,” Anna pointed out, as Adam and Matt began making out again. “So fucking hot.”
The kissing went on for what felt like hours but was only minutes. Matt was kissing both Adam and Anna with fervor and soon enough both the red-ed men had tents in their pants. Anna first rubbed Adam’s hard on and then she placed her hand on Matt’s over his jeans and groped and squeezed it with a big smile on her face. Here she was between two hard hunky men making out with them and watching them make out with each other. It was hot.
The room was spinning. In his drunk state, Matt let Anna fondle him, all reasoning gone out the window from the drinking. Was it Anna’s hand or Adam’s? He really was not sure at this point; he just knew that it felt good.
He felt lips on his and knew them to be Anna’s since they were softer. He groaned against her mouth as her hand continued to squeeze and grip his erection over the fabric of his pants. He got bigger and harder and made no argument when Anna brought his hands to her big tits and made them squeeze them.
When she released Matt’s hands, he continued to clumsily feel her breasts over her blouse. Her nipples were erect, so he stroked his thumbs over them both at the same time, thinking in his mind how soft and feminine her body felt compared to Josh’s. It was not a disgusting feeling, but he was not exactly thinking intelligently either through his alcoholic haze.
Anna broke the kiss with a smug grin on her face. “Do you like my tits, Matt?” She asked, pushing them up for him to continue to grope and fondle.
“Yeah,” Matt answered, on instinct. “I mean, no. I mean I don’t know.” He was so deeply confused in that moment. His head was spinning and all he could think about was having sex with Adam. It was not registering that it was sexual with Anna yet.
“What about you, Adam? Do you like them?” Anna asked, turning to Adam and letting him cop a feel.
“Hell yeah,” Adam answered, like such a typical horny teenager. “They’re great! I would love to suck on them. Would you like to suck on them too, Matt?”
“Uh huh,” Matt answered, not even really registering what he was saying since he was in such an agreeable state. “I’d like to suck on your balls too.” God, he loved to suck on balls as he jerked a big, hard cock. It was clear to Adam and Anna the way that Matt was slurring his words that he was drunk right now.
“Why don’t we play a game?” Anna suggested.
Matt just grunted. Adam tilted his head to the side with curiosity. “What game did you have in mind?”
“Strip poker, of course,” Anna replied, with a devilish gleam in her doe brown eyes.
Adam shrugged nonchalantly. “Nah, I’m not into that. Why don’t we just go to your room and fuck?”
Anna rolled her shoulders, mimicking Adam’s nonchalant shrug. “Nah, I’m not into that.” Even though she was, she did not really feel like giving in to Adam that easily. She was feeling frisky tonight and she was not just going to bend over backwards for the guy that she had just met earlier today.
Adam seemed really annoyed. “You’re a fucking cock tease, girl.” And then he left behind a stunned Anna and Matt.
“Well that was rude,” Anna finally remarked. “He was kind of a prick, let’s be honest.”
Matt shrugged. He had been quiet through the whole conversation between Adam and Anna before Adam stormed out the door feeling like he had been robbed. But Anna did not seem to miss a beat.
She turned to Matt with a grin and then bopped his nose with her finger. “I’ll get the cards! Unless you want to play truth or dare instead?”
Thankfully, Matt was starting to come down from his drunken stupor. “I think I should go to bed.”
Anna pouted, clearly disappointed. “Aw, come on, Matt. Do not be a party pooper like Adam was! I promise that I will make it worth your while.”
Her voice was so sultry and seductive that Matt could not resist. “Okay, fine. Strip poker it is.” Could he think enough to concentrate on it? Well he was going to find out! He figured there was no harm in it. It was just between friends, right? He had already forgotten that just a half hour before Anna’s hand had been playing with his hard cock through his jeans.
Anna squealed with excitement and got the cards. She dealt them a hand and Matt lost the first round so he stripped off his shirt. He lost the second and third hand, so off went first his shoes and then his socks.
“I’m beginning to regret my decision to play strip poker with you,” he joked, laughing loudly. He was more loosey goosey when he was drunk and though he was much more conscious of what was going on right now, he had a long way to go before he was fully rational.
Thankfully, Matt won the next round. “Yes! Alright, um. Take off your shirt first.” He commanded.
Anna just smirked. “Why, Matt, if I didn’t know you were gay, I’d think you were trying to get me naked,” she teased, with a cute little laugh as he rolled his eyes with a smile. Her blouse came off to reveal a pink lacey bra underneath that left little to the imagination.
“Very funny,” Matt quipped, with a smirk. “Next hand. Daddy needs a new pair of shoes!”
Of course, Anna won the next hand. Matt stood up with a grumble about her cheating and unfastened his jeans, letting them fall to the floor. Thank God he wore boxers today. But if she managed to win one more hand, he was going to be at a severe disadvantage here because he would be naked.
Lucky for him the next round was a win for him. Anna chuckled and stood up and stripped off her short skirt. She was now in only her bra and panties, as she had already taken her high heels off the second that she came into the house, so she had a disadvantage over Matt there.
“Maybe we should stop and switch to truth or dare,” Matt said, getting a little uncomfortable with their state of undress. He knew what would happen if he lost his boxers. If she lost the next round, she was going to either reveal her tits or pussy and he wasn’t sure he was so comfortable with that even though he had seen her naked way back when he had spied on her and Brad having sex. That felt like ages ago now, though, and she did not know about what he had seen. He was not about to tell her either.
“God, you are such a prude,” Anna said, with a smirk. She got up and poured them both three more shots and they both drank them back to back.
As soon as his third glass slammed down on the table, Matt’s phone buzzed in his pants on the floor and he fished it out of his pocket and looked at the text that came through and let out a groan.
“Ugh, it’s Josh. He is stuck at work for a few more hours. Looks like he’s finally going to be pulling an all-nighter,” Matt murmured, wondering if that sentence even made sense. Was he making sense? Was anything making sense? His head was feeling fuzzy again from the alcohol he just consumed.
“That sucks,” Anna said, dealing out another round of cards.
Matt seemed to have now forgotten about their state of undress with the alcohol. He wished Adam were still there with them. Their kisses had been super-hot. In the end though he had seemed like a little bit of a stuck-up jerk. Who does not like some good old-fashioned strip poker? Apparently snob nosed bisexual men.
Anna lost the next hand. When she took off her bra, Matt could not help but stare at her now naked tits. Her nipples were instantly hard from the sudden onslaught of cold chilly air. He had a brief flashback of her big breasts bouncing as she rode Brad. He snapped himself out of it and looked at her face, seeing her beautiful smile across the table, and a mischievous little twinkle in her eyes.
“Okay. Truth or dare time. I dare you to feel me up,” Anna said, with a big smirk on her features.
“But I didn’t even choose dare,” Matt objected, leaning back in his seat. “That’s not how the game works!”
Anna scoffed and rolled her eyes. She stood up from her chair and walked over to Matt and straddled his lap, placing her hands on his strong shoulders. As soon as she was settled, she leaned in and kissed his nose. “I dare you to feel me up. You did it earlier without an issue. What is the problem now, Matt?” she asked, with a seductive smirk on her features.
Matt was not sure he was comfortable with the direction of where this was going. Anna rolled her eyes when he made no move to touch her and grabbed his hands and placed them on her luscious round globes. They felt firm and soft all at once in his hands. After a moment of just holding them he began to squeeze and grope them, rolling his fingers over the hard nipples. Maybe it was the alcohol, but they felt good. Soft and pillowy and yet somehow stiff at the same time. It was so different than touching a man’s chest but not entirely terrible.
“Do you like them, Matt?” Anna asked, her voice lower than normal.
“They’re okay, I guess,” Matt said, and then realized that sounded kind of shitty. But he was gay! What did she expect?
“Just okay? Don’t be afraid to tell me how you really feel, Matt,” Anna murmured.
Matt squeezed them more and gave her nipples a firm pinch like he would if he were teasing Josh. This made Anna gasp, so he did it again, pinching and pulling on her hard nips.
“Oh, yeah, just like that!” Anna exclaimed, arching her back to give Matt better access to her firm globes.
Matt squeezed her tits hard, continuing to grasp her nipples between his fingers and give them firm tugs, becoming a bit more aggressive with his actions. It was not long before Anna was writhing in his lap while she let out little purrs and moans of pleasure, grinding down onto the growing hardness between Matt’s legs. He was only in boxers and he could feel her pert ass rubbing along every inch of his now expanding flesh. It was only natural that he was getting a hard on but he was still silently cursing his traitorous organ for responding in such a way to a woman of all people.
Anna leaned in and broke him out of his thoughts as she kissed him deeply. They started to make out as he continued to play with her tits. It was all getting extremely sexual now. Still, he kept fondling her body, his mind in a bit of a haze from all the alcohol he had drank.
But not enough for him to not snap out of it. Matt realized just how serious this was getting. It was too much, and he heard her sigh of disappointment as he withdrew his hands from her body and his lips from hers and held onto the sides of the chair below him. “I think we should stop now, Anna. As fun as this has been, we have let things go too far. I’m gay and this is getting a little too weird for me.”
“Not yet, Matt, please! We are having so much fun, aren’t we? Just a few more kisses,” she begged, panting hard as she stayed still on his lap.
She kissed him again and could not help but kiss her back. He thrust his tongue into her mouth and found himself grabbing her big tits again before he could stop himself, pawing and squeezing them hard. He pinched her rock-hard nipples, enjoying the sound of her squeals against his lips.
When she started squirming on his lap from what he was doing, his erection returned. He was so fucking horny right now it was crazy. He reasoned it had to have been his earlier kisses with Adam. There was no way that Anna was arousing him like this. She couldn’t be, right?
Anna reached down between them and began to grope and stroke his hard cock as they kissed. He slapped her hand away and kept kissing her as an almost apology that he had to do that, his mind getting lost in a haze. She relented for the moment but as their kisses continued, she reached for him again and this time could not find the willpower to stop her.
Matt moaned against Anna’s lips as she squeezed and groped his shaft over the thin cotton of his boxers. Her sneaky hand suddenly left him to slide into the slit in them so she could grip his thick meaty cock within. She started stroking him up and down, jerking him off as he kept feeling her soft, pillowy tits.
Their moans were getting louder as they fed hungrily at each other’s mouths. Matt was too far gone now and wanted to cum. He no longer cared that Anna was a woman, right now it was about sexual gratification. It was not like they were fucking.
“Does that feel good, Matt?” Anna asked, sucking on his lips.
Matt groaned as her fist flew up and down the full length of his turgid rod. “Oh, yeah! I’m gonna cum soon.”
“I want you to cum on my tits,” Anna said, moving off his lap to the floor. She squished her big boobs together and looked up at Matt with a seductive smile on her face. “Fuck them, Matt. Fuck my tits!”
Matt began humping his hips, the feel of her large tits surrounding his big shaft heavenly. He fucked her tits for a few minutes more and felt the familiar tingling in his balls. “Oh, yeah. Oh, yeah!” He gritted his teeth as his release came closer and closer.
Anna lay down on the floor for him and beckoned him over by crooking her finger at him. The urge to cum was too great to deny for him now, so he moved to the floor and straddled her torso, grabbing her tits and pulling them frantically together around his cock. He started fucking her breasts wildly, letting out loud grunts and groans as her soft warm flesh stroked every inch of his large dick.
His breathing and pace sped up and it was not long before his cum was shooting out like a rocket all over her face and open mouth. He pulled back from her and jerked the rest of his seed out of his pulsing and throbbing flesh all over her tits until he was spent and could give her no more.
He breathed heavily, coming down from his high. He watched as Anna used her fingers to collect all his hot sticky seed off her skin before bringing it to her mouth to suck her fingers clean. She gathered a bit more and brought her fingers over to Matt’s lips and he obediently licked and sucked his own spunk off her feminine digits.
“You taste as good as I thought you would,” Anna murmured, a satisfied smirk on her face.
Matt immediately felt guilty over what he had done. Had he just cheated on Josh? He had just felt Anna up and then fucked her tits. It was not like they had fucked or anything, but it had gone way farther than it ever should have.
“What did we do?” Matt asked, mostly to himself.
Anna smiled and sat up, stroking Matt’s face. “It’s fine, Matt. You still have your gay card. It was just a little bit of groping and fondling.”
“Oh, is that all?” Matt asked, his tone sarcastic and upset. “Is that how Josh is going to see it? Just a little bit of groping and fondling?”
Anna shrugged. “Josh doesn’t have to know, Matt. It is not like we did anything bad. So, you came on my tits. Big deal! What do you think could have happened if Adam had stuck around? You might have ended up fucking him. And then you would have really cheated on Josh. So, you dodged a bullet there, right?”
Matt sighed. He was still drunk. That had to be how all of this had happened. “Okay. I really need to go to bed now.”
“Kiss me good night,” Anna murmured, threading her fingers into the hair at the nape of Matt’s neck. He had to admit that he loved it when she did that. And her tone was so inviting that he could not resist her. Kissing her was natural to him now. And he could not deny any longer that he did not enjoy it. Fuck. Was he losing his gay card?
He leaned in and kissed Anna on the mouth. It was intended to be a short kiss, but it never broke. He let out a moan against her lips as they started to make out again. Anna grabbed his hands and brought them to her tits. He squeezed and groped them as if it were a reflex reaction. By now it probably was.
Anna began to stroke his half-hard cock. He batted her hand away and their kissing went on. He let go of her tits and rested his hands on the small of her back. She moved so they slipped down to her ass and he let it go and left them there as their tongues dueled and danced.
Anna moved into his lap on the floor as his hands squeezed her ass over her thin lace panties. When her hand went back to his cock again, he swatted it away once more. But their kisses quickly grew more intense and when Anna went for him again, he did not stop her this time. He had no idea what was wrong with him. He reasoned it was lack of judgment from the alcohol. Would this be happening were he sober? Probably not.
“Please don’t go to bed, Matt,” Anna whispered against his lips, as her hand wrapped around his firm shaft and began to stroke from base to tip. Every time she reached the spongy head, she did a thing with her fingers that felt so fucking amazing that it took no time to get Matt hard as iron again.
Matt brought his hands back to Anna’s breasts. He could not seem to get enough of them. He pinched her nipples and gave them a twist because she seemed to love that. He was now starting to question his sexuality. Never in his life had he ever thought he would enjoy feeling a woman of all things up. He usually preferred hard, muscled chests. Anna was all soft and tender. Somehow, he was enjoying that.
He could feel how wet she was through the thin fabric of her panties as she rubbed her crotch along the full length of him. He knew it would take him some time to cum again. Did he want to again? Hadn’t they gone far enough? His head was spinning, and he felt even more drunk than before. He was not thinking straight at all.
Anna raised herself briefly and wiggled around a little, her tongue trailing over his lips to keep him distracted. Matt felt her grab his cock and then he felt a different sensation than her hand, like a firm pressure surrounding his dick. It felt warm, wet, and silky and it was only seconds before Anna had fully seated her pussy on his turgid flesh.
It dawned on him just what had happened, and he ripped his mouth from hers as he began to go into panic. “No! Anna! What are you doing?! We can’t do this!”
Anna kissed Matt again before he could say anything more and began to bounce on his dick. He tried to grab her hips to pull her off, but she was moving so fast it was hard to get a firm grip on her. That and it was starting to feel good. Really good. Like nothing he had ever felt before ever in his life which made sense because he had only been with one man his whole life. He could feel her pussy pull as she reached the top of his long length, and then soften as she slid all the way back down to grip and squeeze and milk his hard rod balls deep inside of her.
In a last-ditch effort, Matt grabbed her hair and yanked her mouth off his. “This is wrong, Anna! We have to stop!”
“Stop pretending you don’t like it, Matt,” Anna whispered into his ear, as she moaned and whimpered whenever he hit all the right spots inside of her. “God your big gay dick feels so fucking good inside of me, Matt! Fuck me! You know you want to. You like it, admit it!”
“No! I’m gay!” Even to him his protests did not sound convincing at all anymore. He could not believe that he was cheating on Josh with Anna. Was Anna right? If Adam had stayed would it have been him instead? Or would this have inevitably happened between him and Anna anyway? He did not know. All he was aware of was how good her warm, velvety heat felt wrapped around every inch of his stiff naked prick in her unprotected pussy.
“Are you, Matt? Are you?” Anna asked, biting her lip as she rocked and gyrated her hips up and down his thick meaty pole. She had a fair point.
Matt was feeling really turned on now. He reasoned that what has been done was already done. Why turn back?
“Oh, fuck, Anna!” He hissed, laying back on the floor and moving his hands to her hips. He started to thrust up into her with vigor, grunting and groaning as he rammed into her tight little pussy with powerful strokes.
Anna squealed with pleasure, and Matt reached up and grabbed her bouncing tits as she met his thrusts like a wanton whore. “I’ve wanted this for weeks! Fuck me, Matt! Fuck me hard!”
Matt growled as he sank deeper into her and felt himself already getting close. The way she was bucking and writhing, all the new sensations, his whole body was feeling exciting things that it had never felt prior to this. His gay card was out the window now as he eagerly met her wanton thrusts, raising himself up to kiss her and twist and pull on her nipples.
“I’m gonna cum, Anna,” he moaned out, sucking on her tongue as he passionately fed at her lips.
“I want to make you cum, Matt. Cum inside me!” She begged, perfectly squeezing her Kegel muscles around his hard-hung shaft as his thrusts became more and more urgent into her.
That was too much for Matt to bear. He let out a loud yell as he slammed into her as far as he could and came deep inside her milking cunt. It felt so good. He knew by the way her moans escalated with his that she was orgasming with him.
They kissed for a long time afterward and enjoyed the afterglow while it lasted. Anna was the one that slid off his lap and helped him to his feet. She gave him one last kiss with a smile. “I really enjoyed that, Matt. I am going to take a shower. Feel free to join me if you’re feeling frisky and want a round two.”
Matt had no words. He stared at Anna longingly as she left him standing there with his mouth agape. What had he just done? One thing was for sure. He knew that his life going forward was changed forever. Fuck!
Five minutes later, he joined Anna in the shower.
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