Roommates
by sheepisheyes » Mon Apr 08, 2024 1:25 pm
Tommy shared an old house with two roommates. Charlette and Chaz. He answered an ad and moved in. His bedroom was on the first floor off the living room, Charlette and Chaz had the 2 bedrooms upstairs. Charlette and Chaz both had very active sex lives. Not with each other, at least as far as Tommy could tell, but typically on the weekend they had their own partners. Neither seemed to be going steady with anyone and liked to play the field.
It was quickly obvious that Tommy did not do well with women. In the 18 months he had lived there not once did he bring a woman home, where as Charlette and Chaz had to be close to 30 lovers each. Tommy was very jealous of both of them but accepted that he just could not seem to attract anyone. One night Chaz had a gorgeous woman that he brought to bed. It was 1 in morning and Tommy sat on the living room couch so he could listen to them fucking. Oh how he wished it was him. As happens at least once a day, he pulled out his below average sized penis and started playing with it.
This was one of the few weekend nights that Charlette was home and not upstairs fucking away herself. She decided to head downstairs to get a glass of wine since it was difficult to sleep listen to Chaz pounding away. She padded down the stairs and saw Tommy playing with himself. It was no secret to them the Tommy was a chronic masturbator and why he never had any women. She sat next to him startling him as Tommy tried to cover up . “Don’t bother Tommy you poor thing. Are you listening to Chaz fucking? It must be hard for you hearing that and never having any women yourself” She stated.
Tommy started blushing and tried to get up but Charlette stopped him. “Its ok Tommy keep playing with yourself we all know that you masturbate all the time.” She said looking down at his small penis in his hand. “I’m sorry you can’t get any women. I certainly would never have sex with you but its not your fault. You are a beta and women are just not attracted to beta males. You also have a very small penis” she said looking down and giggling. Tommy knew what a beta was. He watched porn all the time and loved the beta jerk off instructions from mean femdoms. Hearing Charlette talk about him this way turned him on. “Its ok if I play with myself now?” he asked her. “Yes its ok. Don’t touch me though. I don’t mind you playing with yourself”
Charlette sipped her wine watching Tommy stroking away. She couldn’t help but think what a loser he is and understand why no women would sleep with him. But he was her roommate and he was kind of sweet in a way. She felt sorry for him really. She could tell Tommy was going to cum soon, his mouth was hanging open with this stupid look on his face and his hand was a blur on his cock. He really did look pathetic. Tommy pumped his hips and little spurts of cum shot out of his penis. Charlette could not help herself and had to laugh at how ridiculous he looked. Tommy sheepishly looked over at Charlette red faced with shame and embarrassment. Above them they could hear Chaz’s girl yelling come in me please. “Poor Tommy. Chaz is filling a pussy and you are filling your hand” she said looking at Tommy with pity.
Chaz and Charlette would have a party on the weekend sometimes. There would be a dozen or so people down stairs having drinks, playing music and talking. Tommy never attended these. He shut his door and stayed in his room. He wasn’t comfortable socializing, especially with the women. Charlette was secretly happy he didn’t participate because he made people uncomfortable. Tommy sat in his room with his pants off and his legs up on either side of his monitor wearing headphones and stroking away to a women telling him what a loser he is. He thought to himself here I am while my roommates and their friends are out in the other room having a party. I really am a loser. Charlette need to borrow his cell phone charger so she knocked on his door but he didn’t hear her. She opened the door and walked in and saw him jerking away. Tommy had no idea she was behind him. She could see the video of a woman talking and realized that was what he was jerking off to. Nothing shocked her when it came to Tommy the masturbator. She walked over and tapped him on the shoulder. Poor Tommy whipped of his head phones, spun around with his hand covering his lubed up penis, sitting there naked from the waist down. Charlette stood there shaking her head “Oh Tommy look at you. It’s Friday night and there is a party going on and here you are playing with yourself. There are a lot of single women our age out there but you chose to jerk off. Do you see why you never have a girlfriend? You are as beta male as it can get.”
Tommy was humiliated but then saw past her and realized she left the door open and a bunch of people from the party were looking into his room at him. “Let me borrow the cell phone charger and then you can get back to jerking off” she said smiling. “Oh I’m sorry I forgot to close the door. Don’t worry they all know what you do. Everyone out there knows you’re a chronic masturbator”. Tommy was mortified as he met eyes with at least 3 beautiful women all laughing and looking at him. “Go ahead and finish. I see the charger” Charlette said grabbing the charger. At this point there was no dignity left for him, so he pumped his cock as everyone watched. Charlette having seen this before walked out and slowly closed the door as Tommy started shooting cum in the air.
As time went on, Charlette and Chaz just ignored Tommy for the most part. Everyone they knew had heard about his masturbation habits. Other than the roommates no one really talked to him. Any women that came to the apartment would give him a sideways glance but otherwise ignore him. He was masturbating more than ever before now that there was nothing to hide, and he was in a constant state of humiliation and arousal.
Chaz’s girlfriend Darlene had heard about Tommy and how pathetic he is. She wanted to meet him. Chaz warned her that Tommy is pretty creepy and extremely shy. “He’ll probably run to his room and jerkoff in the middle of talking to you!” he laughed. Sure enough when Chaz introduced them Tommy just shuffled his feet and looked at the ground. Darlene tried to talk to him, but she was far too beautiful for Tommy. He kept looking at her breasts and stammering. Finally, he headed to his bedroom closing the door. “See I told you” Chaz said. Darlene laughed out loud “Oh my God he really is pathetic”. Darlene had this urge to be cruel to him. She couldn’t quite pin point why but it was a strong feeling.
That night Darlene got fucked good by Chaz. She told him she wanted to go down stairs and see what Tommy is doing. Chaz laughed and said “You know what he is doing. It’s what he does every time one of us is up here having sex”. “I know but I’m curious”. “Go for it, I’m going to sleep”. Chaz had absolutely no jealously what so ever about Tommy. He was the most non-threatening male alive.
Tommy was on the couch masturbating. Chaz had finished but Charlette was still moaning with the guy she brought home. Tommy saw Darlene and tried to run away with is pants around his ankles, but she stopped him. “What the fuck! You sit down here listening to your roommates having sex and jerk off? Do you ever get laid?” Tommy knew there was no point, so he just kept his hand around his penis and answered, “No I’m still a virgin”. “Wow you are pathetic and you’re never going to get laid. Look at you, you can’t even look at me without looking at my tits but never in my eyes. What a wimp.” She sat in chair across from him in her skirt she had put on. She pulled off her panties and tossed them to him. “I dare you not to put these on. A real man would never put these on”. Tommy didn’t hesitate. He pulled the panties up his legs. “That was quick”. Tommy looked down in shame. His little penis fit easily in the panties. You almost couldn’t tell he had a penis, except for the little tent that was forming.
“Crawl to me” she ordered and hiked up her skirt and opened her legs. “Lick my pussy. Its full of Chaz’s cum I think you will like it.” Poor Tommy did as he was told and started licking the first pussy of his lifetime. He’d tasted his own cum but not someone else’s. Darlene’s and Chaz’s together were intoxicating. He felt subservient and submissive and lapped away at her pussy. Darlene moved his head here and there and gave him instructions on how to lick her and please her. When she was done with him she told him to stand up. His panties had a little tent, and his face was glistening with their cum.
“Now you may finish playing with yourself in front of me”. Tommy didn’t mind this at all, as a matter of fact he was getting addicted to the humiliation, and this was extreme. Jerking off in a pair of panties with a face full of cum in front of his roommate’s girlfriend. His hand was instantly in his panties furiously jerking his penis already lubed from when she caught him. Darlene just sat and laughed watching him make a complete fool of himself. It didn’t take long for his legs to quiver, and a little wet spot appear on his panties. “There you go! Now you are officially a sissy. Cumming in a pair of panties! Go ahead and keep them.” she giggled.
Charlette and Chaz both heard what Darlene made Tommy do. Soon so did all of their friends. They lost all respect for poor Tommy and now acted like he didn’t exist. Charlette was a little sympathetic but just could not bring herself around to have any respect for him. He was just too much of a wimp for her. The next time she was going to have a man over for sex she approached Tommy. “Tommy would you like to clean my pussy tonight after Todd fucks me?”. Tommy was beside himself “of course! I would be honored”. Charlette laughed and liked the feeling of power she had over him. “I want you wearing panties too”. “Yes Miss Charlette.” He replied. “Miss Charlette. Hmm I like that.”
That evening Tommy sat on the couch in the dark wearing the pair of pink panties Darlene gave him, listening to Charlette being fucked. He played with his little dick but very careful to not cum yet. He didn’t want his panties wet or Miss Charlette mad at him. Eventually the pounding and moaning stopped and he knew the time was near. This was a dream come true to actually see and lick her pussy, especially after being filled with sperm. He was adjusting nicely to his new sissy status in life.
Charlette approached with a satisfied look on her face and laughed when she saw him with his hand in his panties. “I hope you haven’t cum in those panties” she said. “Oh no Miss Charlette. I just can’t help myself when I hear you being pleased by a real man”. “Yes I can understand that. Well come over here and clean my pussy” she said matter of factly as she sat down and spread her legs. Tommy was learning how to properly clean a pussy and provide pleasure at the same time. He might not be man enough to pleasure a woman with his cock, but his obedience and tongue were getting closer. Charlette pulled her legs back and presented her asshole where cum had drip onto. Tommy didn’t need to be told. He immediately went to work on her asshole as his nose buried into her sloshy pussy coating his face in their slime.
After Charlette was cleaned and satisfied she told Tommy he could now play with himself in his panties, which of course he immediately did. Standing in front of Charlette the smell of her pussy on his face he instantly blew his little load leaving a wet spot in his panties. Charlette laughed and headed back up stairs to be with her real man.
Then an amazing thing happened, Tommy found a girlfriend, Alison. She seemed to like Tommy and they started to hang out together. No sex as of yet but Tommy quit masturbating for 3 days. Tommy hid all his lubricant and tissues. He erased all his porn history and thought he could turn a new leaf now that he potentially had a girlfriend. That evening he brought Alison to the apartment, and they were started watching a movie on the couch. Charlette came home first and was stunned. “Who do we have here Tommy?” she asked. He nervously replied “This is my friend Alison” being careful not to say girlfriend. The greeted each other and Charlette smiled at Tommy. Tommy prayed she would not embarrass him in front of her. Next home was Chaz and Tommy introduced them. He noticed that Alison seemed a little more interested in meeting Chaz, her face was even a little flush.
That evening after Alison left, Charlette came down to talk with him. She actually found herself a little jealous which confused her given what a wimp Tommy is. Maybe she just needed to exercise her power. She walked into his room twirling a pair of panties on her finger. “So, Tommy are you still ready to put on my panties and lick my pussy?”. Tommy’s little boner popped to attention. He stammered “Umm I really shouldn’t since I’m with Alison.” “You told me she was just a friend. Besides do you really think you’ll end up having sex with her? Tommy your cock is tiny, and you wear panties. Get real and get on your knees” She ordered. Poor little Tommy had no choice. He peeled his shorts off and she flung him the panties which he eagerly slid over his hard little penis then he settled in and licked her pussy and asshole for a good hour before she pushed him a way. “Good boy Tommy, maybe Alison will let you lick her pussy, you are getting pretty good at it” she complimented him.
Alison came over again. This time Chaz was in the living room setting up his massage table. He was talking classes to become a masseuse. Alison asked him about it, and he told her that part of his training is to do practice massages and ask if she would like one. Alison’s face flushed and she said, “Sure I would love that”. Tommy felt a knot in his stomach. Something told him this was not going to end well for him. Chaz handed her a big fluffy towel and said to take off her clothes except her underwear and wrap that around her. The flush on her face showed arousal. She went to the bathroom and returned with the towel around her and only her bra and panties underneath.
Chaz had her lay on the massage table on her stomach and folded the towel to expose her back and bra strap but kept her cute little ass and panty covered. Chaz asked if we could unsnap her bra, so he didn’t get it oily. Alison replied almost breathlessly “Yes you may”. Tommy was getting excited. He knew he shouldn’t be and that he should be jealous, but he felt so helpless watching muscular Chaz start massaging oil into petite Alison’s back and shoulders. Next he flipped the towel on her legs up and started massaging her legs. From Tommy’s seat he could just see her little pink panties under the towel. He was sure Chaz could too. As he was running his hands over her legs, Alison let out soft moans and said how good it felt. Chaz then asked her to turn over and handed her a small towel to cover her breasts.
Alison rolled over and told Tommy not to peek. She didn’t say anything about Chaz peeking though. He got a good look at her little breasts as he started massaging her shoulders and ran his hands just a little under the towel covering her breasts. Alison was clearly turned on and she pulled the little towel off exposing her small pert breasts and looked Chaz right in the eyes. Chaz looked up at poor Tommy and winked. Tommy had a full boner now and couldn’t stop watching. He realized he lost her and she was Chaz’s for the taking. Chaz rubbed his oily hands all over her breasts as her nipples hardened to his touch. She lifted her arms over her head so he could have full access to her tits. She was moaning and not trying at all to hide the fact that she was aroused.
Chaz started lower on her stomach as her chest rose and fell with her heavy breathing. “Take the towel off, I don’t care” She said breathlessly. Chad pulled the towel way and now Alison was laying there in only her tiny pair of pink panties. He started on her feet and moved down her legs. Alison was rotating her hips and moaning. There was no hiding what was going to happen. Tommy no longer existed it was just Chaz and Alison now. Tommy couldn’t believe that she was acting like a total slut. Tommy realized that she was not as innocent as he though she was. Soon Alison was almost panting and gyrating her hips as Chaz got closer to her pussy. Tommy just stared as Chaz ran his hands on the insides of her thighs as Alison opened her legs wider. Tommy was staring at the crotch of her panties watching a wet spot grow as Chaz’s hand brushed against it and she gasped out loud.
Tommy knew it was over for him. He was so helpless and humiliated. Chaz sensed this and asked Alison if she would like him to remove her panties. She replied “Yesss” in a heated voice and lifted her little ass in the air to make it easier. He slipped them over her feet, and all could see just how wet her pussy was. Chaz then offer the panties to Tommy saying, “I know you like to jerk off in panties, why don’t you put these on and play with yourself”. This turned Alison on even more, seeing the alpha having complete power of the beta.
Tommy just took the panties, dropped his pants, and pulled them up over is tiny but hard penis. Alison watched and giggled at Tommy. “You’re so small Tommy. I’m sorry to do this to you but I can’t help it and besides we would never stay together with that little thing. Not to mention that you wear girl’s panties”. Tommy stood there looking at them. He looked down at the biggest tent he ever made in his panties, which was not much. Then looked up as Chaz dipped a finger into Alison’s dripping pussy. She moaned and ground her pussy into his hand. Her legs were splayed open as she pushed her pussy into his hand for more.
Tommy realized this was the best he would ever get. “Fuck me! Please! Fuck me Chaz. I want you so bad.” She screamed. Poor little Tommy grunted and came in his panties without even touching himself. This was the hottest most humiliating thing he had ever seen. Alison looked and barely registered the little wet spot on Tommy’s panties and she smiled and turned back to Chaz as he pulled out his massive cock. She gasped and reached out for it. Her little hand looked even smaller holding his now hard cock. She stroked it a few times then pulled him towards her, opening her legs wide. Chaz climbed on the table and slid his massive cock into her dripping pussy. It was majestic and Tommy realized he was privileged to witness such an awesome event.
Tommy quickly got hard again and using his own cum as lubricant put his hand in his panties and started stroking again. Chas and Alison were lost in lust and paid no attention to poor Tommy. Chaz pounded in and out as Alison told him he owned her and she was his from now on. It didn’t take long for Chaz to empty his full balls into little Alison and Tommy to cum again in his panty. Afterwards Chaz went to clean up as Alison laid there with her legs still apart and a dreamy look on her face. She knew she acted like a total slut and loved it. “Poor Tommy. Do you feel humiliated and like a loser? I know you do but I just had to get fucked by Chaz and we would never have worked out. I thought I might like a beta, but I need big alpha cocks.” Tommy just shook his head in agreement. “Can I clean you pussy with my mouth please?” he begged. Alison looked at him with pity “Oh Tommy, yes come here and clean Chaz’s cum out of my pussy.” Tommy got to it and started lapping up Chaz’s cum and Alison’s juices like the wimp he is. “Look at you Tommy wearing your ex-girlfriends panties and licking her freshly fucked pussy after your roommate stole her from you. You poor little boy”.
Tommy resolved disappeared. He thought by having Alison he could turn a new leaf. Now he realized that was never possible. His fate is sealed. He finished cleaning Alison’s pussy as she climbed from the table and wrapped the towel around herself. “Go get me a drink Tommy I’m thirsty” just then Chaz started walking down the stairs in his robe “Get Chaz one too”. Tommy did as he was told and came back with two ice cold beers. Alison was curled up and the couch leaning and cuddling against Chaz in his robe. He handed them their beers and neither of them said thank you. Tommy stood there in only Alison’s panties waiting to be dismissed. “You may go” Chaz said as Alison put her little hand under his robe and around his flaccid cock.
“Hey beta boy. I’ve got a job for you. I want Chaz’s cock hard so I can fuck him again. Since you’re just wearing panties, I think you should suck him until he is hard.” Tommy looked at Alison and could not believe the transformation, just hours earlier she was so sweet to him. He was helpless and honestly attracted to Chaz’s monster cock. Tommy got on his knees in front of Chaz and Alison opened his robe to reveal his cock. It was still flaccid but larger than Tommy is hard. It smelled of sex. Chaz opened his legs so Tommy could get between them. Alison fondled his balls and guided Tommy’s mouth onto Chaz’s cock.
Tommy felt so pathetic and defeated. He could feel Chaz’s cock coming to life in his mouth. Slowly filling is mouth as it grew harder. Alison was kissing Chaz as neither of them paid attention to Tommy sucking away. She let her towel fall away so Chaz could play with her breasts. He looked so alpha with little Alison who moments ago was with Tommy’s now leaning against him offering her body while poor defeated Tommy is frantically sucking on his cock. Alison had her hand on Tommy’s head coaxing him up and down. Soon Chaz was fully erect. He barely fit in Tommy’s mouth he was so huge. Tommy didn’t know how Alison fit him in her pussy. She was much more experienced than he suspected. She pushed Tommy’s head away and straddled the huge cock plunging it deep into her wet pussy on the first try. Tommy could only watch in awe.
“Should we share my cum with Tommy” Chaz asked Alison. “I want it all in my pussy!” she exclaimed. “I know but he has been very good, giving up his girlfriend and cleaning your pussy”. “I guess but I still want it” she whined. “I have a lot, how about my first load goes in your pussy and then Tommy can suck on the rest?”. “Oh, alright I guess so” she conceded. Tommy had never swallowed a man’s cum directly from his cock, but he was ready to. He liked being a sissy. Soon the time came as Alison expertly rode his cock to orgasm. He grunted as his first blast filled Alison’s pussy, then he easily lifted her off his cock as she squealed as Tommy’s cheek brushed against her ass and his mouth engulfed Chaz’s cock. It exploded warm cum into his mouth. Blast after blast filling his mouth to overflowing. Tommy couldn’t believe how much cum there was, especially after filling her pussy twice in the last couple hours. He didn’t care as the warm cum slid down his throat trying to swallow so he didn’t miss a drop.
Eventually his balls where drained and Tommy’s stomach was full. Alison climbed off his lap and Tommy’s head went in between her legs to clean her pussy once again. Eventually they tired of him and sent him off to bed wearing Alison’s cum soaked panties. Tommy took back out all his lubricant and tissues he had hidden since there was no need to pretend anymore.