It’s a hot summer day in 1994. Nowhere is a small, fairly poor, rural Illinois town; the kind of town where nobody locks their doors. Summer seems to be an average 19 year old. He goes to a small community college and works on the weekend’s. He’s kind of quiet and doesn’t like to be around his parents. Both parents have jobs where they have to work the night shift. Summer’s mom works for the hospital and his dad has a factory job that he’s had since he got out of high school. They married straight out of high school when they found out Summer was on the way. Summer was an only child and these days he spent most nights alone at home. When Summer had friends over when he was young, they would play house late at night. Summer would always be the girl. He loved playing that game. Now, Summer only plays with himself and he takes things a bit further.
His mom being fairly young, had a younger sense of style. She had a wide assortment of dresses for Summer to go through to try on. Summer loved to play dress up; the way the materials of the dresses played with her skin; the way it tickled his penis. Summer would pay attention to every detail about the clothes he removed and put back, making sure no one would notice he had ever been there. He would always have plenty of time to play, because neither parent got home before 3 in the morning. The only time he ever seen his parents during the week was for about 5 minutes each morning before he went to school. Each morning after he would play, he would eye his parents to see if they suspected anything. On a few occasions he thought they might have suspected, but they never said anything.
Summer never called any of the friends he used to play with before because they had moved away. Summer had one friend named Pete. Pete was a good friend and Summer didn’t want to lose his only friend by confiding in him. Summer was afraid that Pete would turn on him finding out he like to dress like a slut. Pete came over a few times while Summer was dressed and Summer would usually play like he wasn’t home. Summer would hide in the bathroom, his heart pounding, wondering if Pete had seen him.
At school, Summer wasn’t into sports, and he didn’t have gym, which gave him the opportunity to shave his entire body constantly. His body was always silky smooth. Summer was an average c student who hardly spoke in class. His mind was always drifting to that night and what he was going to do. The family also had the internet, so Summer would think about the character he would create to chat online with; usually a female. Summer almost never said he was a cross-dresser. He loved to make guys cum while they chatted with him. Summer was much more computer literate than his parents, and would erase everything before they had a chance to look.
Summer awoke one Thursday morning thinking back to the night before. He had been chatting with a man for a couple of hours before he came on his cam. Summer was getting hard thinking about it when his mom burst through the door. “Morning sunshine! It’s time to get up for school!” she said. Summer quickly turned to his side so she wouldn’t see he was pitching a tent. Summer calmed himself down, got up, and went into the bathroom to get ready for school. Summer ran a hot shower and stripped down. The water was so hot it turned his skin beat red. Summer began to think back to the man spitting on his hand as he stroked himself. Summer was all soapy and massaging his cock. He took he free hand and began rubbing the outside of his ass, before sliding his soapy finger inside. He slid his middle finger in and out as it burned his tight little hole. He stroked faster and faster, sliding two and three fingers in and out, until he came onto his stomach as he dropped to the shower floor. Summer smeared his hot semen all over his stomach and wiped it on his ass as the hot water poured onto his face. He pulled himself together and finished his bath.
As Summer came down stairs for breakfast, he glanced at his mom to see if he would get a suspicious look. She never even looked at him, but his dad came into the room. Her attention must have been on Summer’s father. A rapping came from the front door. Pete was there to pick Summer up for school, so Summer quickly grabbed a pop tart and headed for the door, saying a quick goodbye. The way to school was a quiet ride. Summer couldn’t help but feel like something was going to happen that day. It was an average day at school, but Summer couldn’t shake the feeling. He decided to just stay at home that night, just to be safe.
The ride home from school was equally as quiet. Summer was anticipating getting home so he could change and get on the net. As Pete dropped off Summer, Summer told Pete he was going to his grandmother’s for dinner that night. This was to help ensure Pete did not make a surprise visit. Summer scuttled to the door, slightly shaking his ass, then glancing back to see Pete pulling off not admiring the beauty of Summer’s little ass. Summer ran inside peeling off clothes as he raced to his parent’s room. He stood in front of his mother’s closet, naked, searching for the perfect outfit. Summer found the perfect outfit in the very back; it was a cute little French maid outfit with all the accessories. Summer jumped into the garter belt, then slowly pulling up each stocking making sure they were perfect before clasping them to the garter. Next, she put on the cute little dress taking his time as he put one the sleeves. He put on the heels and checked himself in the mirror. His crotch began to hurt as it tried to burst from his panties.
Summer tried to calm himself before spraying some perfume and leaving the bedroom.
As he cat walked down the hall glancing at his clothes tossed across the floor, he heard a knock at the front door. Summer dropped to the floor, and his heart started to race. Was it Pete? He told Pete he wouldn’t be home. He wanted to look so bad, but he turned and ran straight for the bathroom. Summer heard the front door open, and his heart began to pound out of his chest. He was so scared. If it was his parents, his clothes were everywhere and his was dressed in his mom’s lingerie with no way to change. If it was someone breaking in, he was dressed like a girl and he couldn’t run. If he went outside everyone would see him. He heard someone walk past the bathroom and he froze. The footsteps quickly went to his bedroom and then back.
Summer was petrified as the door flew open and Pete was on the other side. “What the hell are you doing?” Summer couldn’t mutter a word. He stood there like a deer in the headlights. Pete was just as shocked. Pete stood silently in front of the door for what seemed an eternity before muttering, “I didn’t mean to barge in on you like this.” He couldn’t take his eyes off Summer. Summer couldn’t tell if it was a good thing or bad. Summer stepped toward Pete and said, “let’s talk about this in my room.” Summer led Pete toward Summer’s bedroom bending over to pick up clothes making sure his ass was in perfect sight of Pete as the panties would peek out from the dress.
Summer sat Pete down on the bed. As they sat next to each other in awkward silence, Summer thought of what he should say. At least Pete was still there, and not running down the street screaming his head off. At Summer mustered up the courage to say something, Pete swooped in and planted a deep passionate kiss, placing his hands on Summer laying him down on the bed. After a very long and wet kiss, Pete explained how he had seen Summer many times, and couldn’t take it anymore. Pete kissed Summer as he ran his hand gently up and down Summer’s chest and stomach before pulling Summer on top of him grabbing Summer’s ass and sliding his dress above his hips.
Summer kissed Pete’s neck, nibbling on his ear, and rubbing his hands through Pete’s hair as Summer grinded on Pete cock. Pete had his hands on Summer’s waist, sliding his hands behind his panties so he could slide a finger into Summer’s wanting hole. Summer tightened up and moaned as Pete his big finger into Summer’s hole. They rolled over again and Pete leaned up and unbuttoned his pants. Summer said, “That’s my job stud.” Summer reached up and began to rub Pete’s massive cock through his pants. The tip was peaking out of Pete’s jeans. Summer ran his finger back and forth over Pete’s tip as it jumped with every touch. Summer leaned up pulling down Pete’s jeans exposing 8″ in Summer’s face. Summer couldn’t resist and gave it a kiss. The massive rod bounced with the touch of Summer’s lips. Summer started off only working a couple of inches at a time, and slowly working all the way to about 7 before he couldn’t take anymore and slid it out. Summer was bound and determined to take all 8. It took about 5 minutes before Summer had all 8 and was tickling Pete’s balls with his chin.
When Pete got close he pushed Summer off of him, and spun him around. He wiped a big portion of spit that had collected on Summer’s face, pulled his panties to the side and wiped it on his ass. Pete slapped his massive cock across Summer’s ass a couple times before giving a good push. Summer’s ass tried to spread, but it hurt way too much. Summer jerked forward, planted his face in the pillow and to Pete to lick it before you stick it. Pete plunged his face into Summer’s ass licking all around the rim in little circles before spitting all over the hole. As spit drip from Summer’s rear Pete buried two fingers inside. Summer gripped the bed sheets tight as possible as he moaned in ecstasy. Pete slowly slid his fingers all the way in and stopping just before he got out. After they were sliding in and out nicely, Pete would bury another finger working up to 4. When Pete got to four, Summer was panting and moaning, as he reached back to rub Pete’s cock.
When Summer was nice and loose, Pete stripped him down. Now Summer was buck naked in front of a rock hard man for the first time. Pete lay on the bed as Summer straddled him. Pete’s cock was still a lot to handle for this little cd. It seemed to rip Summer’s ass apart as he sank onto it. Summer slowly worked Pete’s massive rod; it hurt extremely, but Summer didn’t want it to stop. After a few minutes the pain turned to pleasure as Summer noticed that he had picked up the tempo. Pete slapped Summer’s ass and said, “Yeah, that’s my good girl… Ride me baby!” Summer blushed as he began to buck faster and faster. Summer leaned down, and bit Pete’s nipple as he rode Pete. Summer could feel the cum building inside Pete’s cock. Summer gripped it the best he could with his ass and began to thrust hard all the way up and down until he could feel the warm semen explode into his ass.
Summer collapsed on top of Pete with Pete still inside him. Summer could feel Pete as he went soft inside him. After about 15minutes of lying in silence, Summer asked, “Does this mean that your o.k. with this?”, as they laughed. Summer stood up, put on a robe, and went downstairs to make and in-between sex snack. As Summer gathered the things for a snack, Pete dripped from Summer’s rear and onto the back of his leg.
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