Before I get into this story, I would like to cover an administrative detail. Many of my readers have been unable to locate my other stories. The following is a list of the story titles and they can all be found under Prolific Authors / Twonight:
Black Dorm World's Hottest T-Girl The Awakening Star Cruiser The Inmate Shocking Encounter Olympiad Turning 18 The Gamblers The Realtors The Kidnapping The Fluffer
Please send feedback to twonight@excite.com. I really enjoy hearing about your first sexual encounter so tell me about it.
As I mentioned above, I really like to hear about my readers' first sexual encounters. I have gotten a lot of great stories. Although I can't vouch for the validity of them, I decided to share a few of them with others, with the names changed and no references which would reveal anyone's identity.
Ok, on with the story:
Gary's first encounter
Carl and his older brother Greg were both in high school. Carl's friend Gary was spending the night with him while Carl and Greg's parents were out of town. Greg wasn't thrilled with having Gary around because he thought Gary was "queer". Carl ignored him and Gary showed up around 7PM. He and Gary went out for some pizza and met some other friends at a movie. Greg went out with his girlfriend Sharon, but they had a fight and he came home early, angry, and horny. Sharon was about to suck his dick when they got in the fight, so he had a bad case of blue balls.
Carl and Gary showed up about 11PM and were sitting in the family room watching "Real Sex" on HBO when Greg walked in the room. When he entered, the segment on the screen was about male strippers. Carl had gone to get them something to drink, so Gary was alone in the darkened room. He didn't hear Greg come in and had no idea that Greg could see him rubbing his cock as the muscular men stripped and waved their big dicks in the camera. Gary was hard as a rock watching the cocks and asses gyrating in front of him. Carl walked back in the room and Gary covered himself with a pillow.
"Hey Greg, sup?," Carl said and Gary turned to see Greg standing in the shadows, smiling.
"Not much, queers. What are you two watching?"
"Shit," Carl said. "It was showing girls getting their tits painted when I left the room. Turn that to something else, Gary."
Gary turned to a movie and they watched the rest of it before heading for bed. Carl went to the kitchen to take their empty glasses, leaving Gary alone with Greg. Greg turned to head for bed and as he passed Gary he whispered, "I saw you jerking off to those naked men, Queer. If you don't want me to tell Carl, come by my room after Carl goes to sleep." With that, he was gone. Gary wondered if he was serious, then decided that he must be. He wasn't sure what to expect, but didn't want Carl to find out, so he decided to comply with Greg's demand.
About an hour after they went to bed, Carl was sleeping soundly and Gary decided to make his move. He slipped quietly out of the room and walked down the hall to Greg's room, opened the door and entered, closing it behind him. Greg was awake and turned on the light.
"'Bout time bitch," he said and slipped off his briefs. His cock hung between his legs and Gary thought to himself that he had never seen anything more beautiful. He had seen longer, thicker ones on cable or in magazines, but this one was about to be his to pleasure. "What do you want me to do, Greg?," he asked, a bit nervous at the prospect.
"Suck my dick," he replied bluntly.
"I've never sucked a guy before," Gary confessed. Strange how he was a bit embarassed to admit it.
"How has a queer like you never sucked a dick?"
"I don't know. I haven't exactly advertised that I like men."
Greg decided to move on and he made Gary get on his knees as he sat back on the bed and spread his legs to give Gary easy access. Gary breathed deeply and went for it. First he stroked it and Greg moaned in pleasure. Then he licked the shaft in the spots that were most sensitive on his own dick. That elicited deeper moans. After Greg's cock was really hard, he took it in his mouth, taking care not to bite. Now Greg was really hot and Gary was pleased that he was doing so well. He began to bob up and down on Greg's cock, licking and sucking as he took as much in his mouth as he could, without gagging. Greg began to run his fingers through Gary's hair, occasionally holding it in place and fucking his face. With each minute that passed, Greg seemed to be getting hotter and hotter. He writhed and moaned under Gary's oral onslaught, bucking to get more of his dick in Gary's mouth.
When Gary moved down to lick Greg's balls, Greg let out a loud moan. Gary worried that he was going to wake Carl. Greg grabbed his cock and began to slap Gary's tongue playfully, then shoved it back in his mouth. After he repeated this several times, he made Gary lay on his back on the bed and he straddled his face, shoving his cock back in. Then he began to fuck Gary's mouth like he was pumping his girlfriend's pussy. Gary just tried to give him a tight sheath with his lips and tongue. After a few minutes of this, Greg started to hump his face even faster, then bellowed and forced his cock all the way in. Ribbons of cum shot from his cock and into Gary's mouth. Gary could barely breathe, but he didn't dare screw up Greg's orgasm, so he held his breath and took it. After the first few shots of hot cum went down Gary's throat, Greg began to hump him again to drain the last of his load. When he finished, he rolled over and sighed deeply. Gary lay on the bed contemplating the strange taste of Greg's cum in his mouth. It wasn't what he expected. It was salty and pungent, but strangely erotic. He loved the hot sticky feel of it as he savored it before finally swallowing.
Gary got up to leave, but Greg stopped him. "Where the fuck do you think you're going?," he asked.
"Back to bed. I sucked your dick like you asked me to."
"Yes you did and now you're going to get me hard again and I'm going to fuck you."
Gary froze, scared and excited at the same time. He had always wondered what it would feel like, but he was afraid of the pain. He knew that Greg was not going to give him a choice so he returned to the bed. He asked Greg if he had any lube, so Greg went to the kitchen and got some cooking oil. When he returned, Gary had stripped and was stroking his cock.
"Look at you, you fucking whore. You can't wait to get my dick up your ass."
"I do wanna try, Greg, but I'm afraid it will hurt a lot."
"Alright bitch, I'll take it easy on you. Now suck me some more and get me hard."
Gary got on his knees and took Greg's limp member back in his mouth. He licked and sucked it until, finally, it began to grow hard again. Soon it was fully erect and Gary was having second thoughts about taking it in his tight, virgin ass. Greg positioned Gary on his knees and dipped his fingers in the oil. He carefully inserted his index finger about an inch in Gary's butt. Gary braced for the pain, but it really wasn't too bad. Greg pushed deeper and the first twinges of pain came. As Greg began to finger fuck him a bit, the pain lessened and Gary's cock grew harder and harder. It was a strange sensation, but very sensual. After a bit, Greg inserted a second finger and resumed finger fucking him. Gary took a bit longer to adjust to the pain, but it eventually turned to a kind of pain/pleasure combination.
Greg decided to try a third finger and it took Gary's breath away for a moment. The pressure was intense and he wasn't sure he could handle it. He asked Greg to remove the third finger but, instead, he just paused with his fingers in to the hilt. Gary caught his breath and tried to relax. After he rested for a minute, Gary told Greg to continue slowly and he did. After a couple more minutes of being fingered, Gary told Greg to try to get his cock in. Greg quickly complied.
After positioning his cockhead at the entrance to Gary's butt, Greg pressed forward, with no success. He tried twice more with the same result. Gary told him to try more lube, so Greg lubed Gary's ass and his own cock one more time. The next attempt got Greg the opening he needed as his mushroom-shaped cockhead slipped in about an inch. Gary squirmed beneath him, but held his ground, waiting for more dick. Greg quickly obliged, forcing two more inches into Gary's tight hole. With a few more thrusts, Greg was balls-deep in Gary's ass. He waited as Gary caught his breath, then began to fuck him with slow strokes, allowing Gary to adjust to this new feeling. Gary was still having difficulty adjusting to this anal invasion, but his cock was as hard as it had ever been. Greg reached around and stroked him, causing a wave of pleasure to sweep through his loins.
The stroking that Greg was giving him made him forget the remaining discomfort and accented the pleasurable fullness he felt in his ass. With each stroke of Greg's dick in his ass, the pleasure increased and the discomfort subsided. Greg's moaning just added to the wonderful eroticism of the situation. Gary turned to his left and saw their reflection in a mirror. He was struck by how sexy it looked to see Greg's body coupled with his as if they were a single unit, joined at their hips by pure lust. Greg now moved his hands to Gary's hips so he could thrust deeper and faster. Gary took over the stroking of his own cock. Soon Greg decided that a change of position was in order, so he flipped Gary over and mounted him in the missionary position, pushing his spread legs back to give him room to thrust deeper into Gary's hot hole. Gary resumed stroking his cock, staring into Gary's eyes and smiling at the combination of lust and bliss that he saw there.
Suddenly, Gary felt a tingle in his balls and his cock began to twitch as his load gushed from his cockhead, splashing on both their stomachs. This seemed to get Greg very excited and he began to pant heavily and quickened his pace. Gary was amazed at how hot it was to see a man's cock penetrating him, using his ass to reach orgasm. He couldn't imagine anything more erotic. He knew that this was not going to be the last time this happened. He planned to get all the cock he could get his hands on. He just wished that he had another cock to pleasure while Greg fucked him. His thoughts were interrupted by a loud growl from Greg. "Oh fuck, I'm cumming," he yelled as he buried his cock to the hilt and began to shoot hot cum deep in Gary's butt. It seemed to go on forever, but still ended too soon.
He assumed they were done as Greg slowly withdrew from his butt, but Greg had one last demand. "Clean my cock," he sneered, offering his dripping cock. Gary did as he was told and sucked the remaining cum from his cock. Gary knew he should be disgusted by taking Greg's cock straight from his ass into his mouth, but he found it very erotic. Finally Greg was satisfied and said "Good job, Queer. Now get the fuck out of here. I'm tired." Gary did as he was told and headed back to bed with cum running down his inner thighs and the taste of jizz in his mouth.
As he climbed back in bed, he realized that Carl was awake. "How was it," Carl asked causing Gary to panic.
"Does he know?," he wondered.
"I heard you two in there. I stood outside the door while he fucked you," Carl said.
Gary started to deny it, but he knew it was pointless. "It was nice," he said.
"Did it hurt?"
"Yes, but that passed. At the end it was great."
"Are you going to do it again?"
"Yes, I am. I really enjoyed it. I hope you don't hate me."
"I don't hate you. I wanna fuck you."
Gary was stunned, but recovered quickly. Instead of a verbal response, he got on his hands and knees and waved his still-lubed ass at Carl. Carl slipped out of his briefs in a flash and moved behind Gary. He wasn't quite hard enough, so Gary began to suck him, causing him to moan loudly. He soon rose to the occasion and was positioned behind Gary again. This time he penetrated easily and quickly began to fuck Gary's hot ass. Carl was so horny that he just pounded Gary relentlessly. Gary didn't mind because he was getting more of what he craved - dick. Within a few minutes, Carl exploded in his ass filling it with more hot cum. Gary surprised him by swinging around and sucking the remaining cum from his cock. When Carl was drained, Gary needed release so he began to jerk off. He was close and soon began to pant heavily as he neared orgasm. Just before he came, Carl dove on his cock and took it in his mouth. Just as he began to suck, Gary erupted and shot hot cum in his mouth. Carl kept sucking until he had every drop of Gary's load.
The guys went to bed and slept soundly until about 6AM. Gary was awakened by Carl's cock knocking at his back door. He wasn't lubed enough, but Carl got some lotion and it did the trick. Carl rode Gary like a bucking bronc bringing Gary to a roaring orgasm. He kept fucking and fucking until, finally, he shot his own load in Gary's butt.
Gary knew that he was going to be spending a lot more time with Carl.
As always, send comments to twonight@excite.com. Check out my other fiction stories, Olympiad, The Gamblers, Black Dorm, The Awakening, The Inmate, Turning 18, The Gambler, The Realtors, The Kidnapping, The fluffer, and Star Cruiser - and my nonfiction Shocking Encounter and Tess' story - World's Hottest T-Girl.