Fantasy, Anal, Bi-sexual, Blackmail, Blowjob, Boy, Boy / Boy, Consensual Sex, Exhibitionism, First Time, Incest, Lesbian, Male/Female, Masturbation, Oral Sex, Teen, Teen Male / Teen Male, Teen Male/Teen Female, Transsexual, Voyeurism, Young
Part 2 of a story about a peeping teen boy becoming curious about playing with dick, peeping on his mother fucking and more....
Sunday night my mother invited her new boy friend over for dinner. My 15 year old sister would not be back from her trip at her best friend Jena's relatives until Monday night. My mother introduced me to Brian as soon as he arrived. He seemed nice, he was younger than my mother and in very nice shape, it looked like he defiantly worked out. We had dinner and then my mother suggested I spend the night at my friend Matt’s house across the street. I may have only been 14, but I knew what this meant, she wanted some privacy so they could fuck. I spent a couple of hours over at Matt’s place. Matt was my age, we had a lot in common, more recently our interest in internet porn. Matt had his own computer in his room and we often checked out porn pictures and videos. That night Matt was excited I came over. "Wait until you see this." He exclaimed as he closed the door to his room. Soon we were scrolling through pages of naked women, each of us with hard-ons. He brought up a movie of a sexy woman stripping. Something seemed funny about the woman; at first I couldn't place my finger on it. She took off her bra revealing a nice round rack of tits, probably fake. Another minute went by then she pulled off her panties and my jaw almost hit the floor. She had a cock! "It's a transsexual." Matt explained, "She has tits and a cock." The Tranny was now slowly stroking her semi-hard penis. I was totally turned on. I had never really thought about liking any other cock except my small 14 year old dick. But watching the tranny lay down and start to stroke her cock while grasping one of her tits really turned me on. Soon the tranny was sucking a man’s cock, then the man started sucking the trannies cock. I had always wanted to have a girl suck my dick, this made me start to wonder what it would be like to give a blow job. After a minute of oral sex, the man started fingering the trannies butt, then he started fucking her ass. At first the tranny made it look a little uncomfortable, then she seemed to start to enjoy being butt-fucked. “I wonder if that feels good?" Matt asked. I told him I didn't know. Pretty soon I was so worked up that I needed to relieve myself. Matt and I never talked about jerking off so I decided to head back home, who knows maybe I can catch my mom in the act with her new boy friend.
I peeped in the windows and saw my mother and Brian making out on the sofa. He had one hand up her skirt and the other wrapped around her. This lasted about five more minutes and then they got up and went to her bedroom. This was my cue. I quietly opened the front door and crept up the stairs to my bedroom. I took off my pants, my dick hard in anticipation of what I was about to witness. I peeped through the floor vent. I saw my mother and Brian standing up near the entrance of the bedroom, embracing each other and passionately making out. She was groping his ass and he was grasping onto one of her tits. After a little
while they broke their embrace, my mother pushed him into the bedroom and up against the wall, right below the vent I was peeping through. She removed her skirt and top and got on her knees and pulled down his pants. His huge semi-hard dick flopped out. My mother then started stroking it. His dick like mine was uncut, but his must have been at least 7 ½ inches and thick. Soon he had afull blown erection and my mother started to suck his dick. I started stroking my dick; it was wet with pre-cum. Brian sighed and
threw his head back and catching me peeping through the vent! I froze instantly. He saw me, smiled and winked at me while nodding his head. Then he dropped his head back down to focus his attention on my mother who was sucking and stroking his boner. I couldn’t believe he had just seen me, but he didn’t seem to care so I kept watching while slowly stroking off. While my mother gave him a blow job she used her free hand to take off her bra. Soon he pulled her from her knees and they stated kissing again. He pulled off her panties and led her to the bed. She lay down on her back and he spread her legs and started eating her pussy. She moaned and occasionally twitched with pleasure. Brian was on the bed on his knees with his face buried between my mother’s legs, he had one hand on one of my mother’s tits and the other was stoking his dick. I now could see very little of my mother, but I was looking right at brains ass which was perched in the air facing me. I had seen a few men’s asses in pornos but his looked strange, then I realized that like the trannies ass I saw when I was over at Matt’s, his ass was shaved! I started to fantasize about walking down stairs and taking advantage of that hole staring at me. I started stroking faster as I thought of fucking my mother’s new boyfriend ass while he ate her out. I quickly climaxed, shooting cum all over my bedroom floor. I continued to watch them; soon he was fucking my mother like no tomorrow. This was actually the first time I had seen people fucking. My mother came first, screaming and gasping, Brian continued for about another minute before he pulled out of my mother and shot a huge load all over her tits. They lay still for a while then began to kiss, then my mother turned off her lamp and they slept.
I slept in the next morning, when I awoke both my mother and Brian were gone. Shortly after getting up I went into my sisters room and grabbed the rest of the pictures of her and Jena having sex. I was just about to jack off to them when I heard the front door of the house open. It was my sister. I pulled up my shorts and started playing a video game. My sister came upstairs and went into her room, she didn’t say anything to me as she passed my open bedroom door. She was in her room for a few minutes then she went back downstairs and took a shower. After her shower she came back upstairs, I saw her pass my door, her hair was wet and she had a towel wrapped around her body. She entered her bedroom and shut the door. A few minutes went by then I heard something slam in her room. Shortly after that she stormed out of her room into my bedroom. “Have you been going through my dresser?” She yelled. She now was wearing a pair of sweat pants and a t-shirt with no bra. Until finding the pictures of her and Jena I had never thought sexually about my sister. But now looking at her hard nipples pointing at me through her t-shirt I was really turned on. “Why.” I replied. “Because there are some things missing from my dresser.” I suddenly thought of a great idea, that I might be able to blackmail my sister into sucking my cock. “You mean these.” I said, holding up the packet of pictures. “Give me those now!” she yelled. “Only on one condition I said, “Only if you…….give me a blowjob.” “Fuck you; you little perv, I’m not sucking you dick, that’s sick, you’re my brother.” She said. “Well then I guess I will have to tell your boyfriend Jake and Mom about you and Jena’s 'relationship’.” I said. “I am not going to give you a blow job.” She reaffirmed. “Okay,” I said, “how about you just strip down and let me see you naked, then I will give the pictures back.” A sly grin crossed my sisters pretty 15 year old face. “Okay.” She said. My dick was almost instantly hard. She slipped off her t-shirt revealing her firm D-cup breast. Then she slipped of her sweat pants, revealing to her little brother her 15 year old pussy. Unlike in the pictures her crotch was no longer shaved, instead she had a narrow strip of blonde pubic hair. “Now give me the pictures.” She said. “Hold on a couple of minutes.” I replied as I dropped my shorts and grasped my hard penis. “Gross.” My sister said. “I don’t want to watch you whack off.” “Well than close your eyes.” I said. She sighed and just stood there. I was so turned on that my sister was watching my jack-off. I wondered if it turned her on as much as me. I couldn’t believe what was happening, I was jerking off, staring at my sisters crotch. I didn’t take long before I was shooting a huge load all over me belly. My sister laughed after I was done then she walked over and grabbed the packet of pictures, then she turned around and left my bedroom, stopping to grab her sweat pants and t-shirt off my floor. I admired her sexy ass while my dick still twitched from its recent ejaculation. I was amazed at how much I now desired to fuck my own sister.
That evening I snuck over to Jena's house. I went into her back yard and slowly crept up to the basement window I had left unlocked. I saw a light on in the basement as I approached. When I peeked into the window I saw Jena's father Mr. William’s working at his workbench in the basement. "Shoot!" I thought, I'll never be able to sneak in with her parent’s home. I would have to wait until they were not around. Jena's Mother Cathrine, everyone called her Candy, was home most of the time, her father went to work during the days. I knew I would have to be more cautious sneaking in, especially with my luck lately. I would have to wait until both her parents were gone. I went back home disappointed. A couple of days later I was over at Matt’s house. His parents left for a couple of hours and before long we were both sitting in front of his computer pitching tents. We were watching some porn when Matt said "What did you think of the Tranny porn we watched the other day?" I told him that it really turned me on, which it did. Since my sister had taken back the pictures of her and Jena I had been thinking a lot of the tranny porn when I jerked off. I was beginning to get real curious about playing with another penis like she did in the video. I wondered what it would be like to suck on one like I saw my mother doing to her boyfriend, or even just watching another man jerk off. "Let’s watch some more tranny porn." I suggested. A few clicks later we were watching a tranny getting butt fucked while she sucked a cock. I asked Matt if he ever jerked off. "Ya, like twice a day." he replied. "Me too." I said. My curiosity overwhelmed me and catching Matt quite by surprise I dropped my swimming trunks and looked at Matt. At first he seemed uncomfortable; although soon he was staring with great interest at my hard dick. "Can I see yours?" I asked after a minute. Hesitantly without saying a word Matt dropped his shorts. His dick was about the size of mine, it was a little thicker and he was circumcised. I focused my attention back on the video and started slowly jerking off. Matt told me to wait a minute and got up and pulled out some baby oil from under his bed. It hit me all of a sudden, he always smelt like baby oil and now I knew why. "Try this" he said as he squirted a little in his hand and handed the bottle to me. I did the same and soon we were both beating our meat. I had never jerked off using lubrication but I liked it, it felt so much more intense that what I was used to. We both watched the video but not for long, soon we were just looking at each other’s dicks as we stroked them. I suddenly felt an overwhelming urge to stroke Matt’s boner. I stopped stroking mine, and Matt paused, I reached over and he did not object. I grasped
his dick. I felt so much different than mine, it seemed hotter, and softer. I started stroking him and he moaned. Soon he was stroking mine as well. It didn't take long before I felt Matt’s cock start to pulse, he gasped and shot a load so far it hit him in the face. He started stroking me really fast and I shoot a load hitting his legs and hand. "That was cool," he said, "but we can't tell anyone." I agreed. We cleaned up and spent the rest of the afternoon playing video games. We didn't speak of what happened for the rest of the day.
The next night we had dinner and Brian came over to join us. My sister Kristen had Jena over for Dinner too.
We talked about the usual stuff, I gawked as usual the whole time at Jena, her pretty eyes and plump lips. Jena mentioned that her parents were going to take her little sister to camp out of state this weekend and that they would have Jena's house to their selves. I knew this would be my opportunity to sneak a peak of Jena, and possibly my sister too.....