OK, I've been very surprised and pleased at the reception my last work has received. I've gotten quite a lot of good feedback about my previous story "Older Cousin." So much so, that I'm pleased to present the next chapter: "My Mother's Boyfriend's Roommate." WARNING: The following story contains man/boy sex. Do not read further unless you are over 18 (21 in some areas), are not offended by such writing, and it is not illegal in your area. Permission granted to store on the Nifty Archive and to distribute electronically as long as nothing is charged for it. OK, my parents were divorced when I was about 9 years old. I lived with my mom and when I was about 13-14, she had a fairly serious relationship with another man. Well, he was serious anyway. To be honest, I think my mother was just in it for the sex. She was 39 at the time, and her "boyfriend" was only about 25. He was in the Air Force, a mechanic I think. Mom and I started spending weekends and vacations over at his trailer. To the best of my memory, he had a cock that was at least 12". Now, mom's boyfriend, his name was Tony, never did anything with me, but he didn't like to wear underwear around the house. He also had a preference for cut off jeans which lead to his pecker sticking out of the leg a lot when he was sitting down. That's how I know how big is pecker was. Tony's roommate's name was Len. He was also in the Air Force. Tony and my mom liked to go out and party a lot on Friday and Saturday nights. Len was a stay at home type, and he and I got along great right from the start. Len acted like an older brother. Since I was the youngest of three, and the only boy, I really enjoyed having an "older brother." Mom had no problems letting me stay with him while she and Tony went out. After they went out, Len and I would normally sit on the couch and watch TV, or rent a movie. I've always been a "touchy/feely" person and even though the couch was big enough for us to sit without touching each other, I'd always snuggle up close to Len. Either he'd put his arm around me, or I'd put my head in his lap and we'd sit quietly and watch whatever was on the TV. To be honest, I didn't think there was anything sexual about it at the time. It was just comfortable. During the commercials or boring parts, we'd talk or wrestle on the couch. Len quickly discovered I was very ticklish and soon, that was his favorite form of attack. As soon as a commercial came on, he'd pin me to his lap with one hand and run his fingers up and down my sides while I rolled helplessly on his lap, back and forth pretending to try and get away. He'd stop as soon as the commercial ended, and I'd return to my place next to him, or put my head back on his lap. I tried to give as good as I was getting, but I rarely succeeded. He was older and stronger than me. Whenever I tried to get even, he'd just hold me down and start tickling me. I was only able to get him back with Tony's help. We would gang up on Len and while Tony held him down, I'd tickle him until he couldn't see straight. Once I even ticked him until he lost control and started peeing on himself. Of course, he got revenge that night. While he didn't make me lose control, he did tickle me on and off (more on) for the entire movie "Dune," the long version, 2.5 hours. He only stopped when I was gasping for breath. He'd allow me to rest for about 2-3 minutes then start again. You can bet, I never tickled Len to that point again. I did get even for the extended tickle attack thou. The next day, Mom, Tony, Len, two or three neighbors and myself were all playing Trivial Pursuit. The adults were in chairs and on the couch while I was laying on the floor. Len had to step over me on his way to this kitchen to get a drink. On his way back, I reached up, snagged his shorts and pulled them down around his knees. Len wasn't wearing any underwear and ended up flashing everyone present. It took him a few seconds to realize what I had done and then he practically jumped into his seat and hid his crotch with his hands. I've never seen anyone turn as deep a red as he did that night. Our relationship changed shortly after that. One of Tony and Len's friends was getting out of the Air Force and they decided to have a big party for him. On the night of the party, Mom "banished" me to Len's room along with a TV and my Atari. I was supposed to stay in the room, play video games, and in general, keep quiet and not disturb the party. One look at the guests, and I didn't want to be around them anyway. Mom was afraid that once they got drunk, I would hear and see things I shouldn't be hearing and seeing. I was happy to stay in the room and play Space Invaders. I stayed up until about 11:00 reading comic books and playing with the Atari. I normally slept on the couch in the living room, but since there was a party going on in there, I stripped down to my briefs and climbed in to Len's bed (I'd been sleeping in my underwear ever since I was 9 or so). Some time during the night, I felt the covers pulled back and heard Len tell me to scoot over so he could get in the bed. Len only had a full sized mattress but I figured we could both be comfortable. Once he was settled, I moved close, snuggled up to him, back to front (his front, to my back) and went back to sleep. I woke up in the middle of the night and we were still in the same position, but Len's arm was wrapped around me. I moved his arm, got up, used the bathroom and then started to climb back in bed. It was then that I noticed Len wasn't wearing anything. Well, since I was at the age where I wanted to seem "grown up" I quickly pulled off my underwear, crawled back in bed and resumed my position. Len woke up enough to drape his arm around me again then fell back asleep. I squirmed against him until I found a comfortable position and joined him. I woke up again, sometime before dawn when Len threw the covers off, shifted his weight and got out of bed. I heard him in use the toilet and then come back in the room. I was still laying there, pretending to be asleep hoping he'd hurry up and get back in bed (I was getting cold with the covers thrown off and my rear end exposed like it was). I heard Len standing there, breathing, and then finally he got back in bed. He tossed and turned, trying to find a comfortable way to lay down, without disturbing me and finally, he had to return to the positions we were in before he got up. However, he didn't press himself tightly against me this time and I was still cold. I sleepily reached behind me blindly and searched for his hand. I brushed against his chest and then traveled down until I hit his crotch. At that point, he put his hand in mine (presumably to stop my searching) and I pulled his arm back over me. This forced him to scoot over against me again. We ended up i! n the same position, but this time I felt something poking me in my butt. I didn't think much about it and started to go to sleep again. This time, however, Len was awake (and sober) enough to realize where his cock was. He also knew where his hand was. Instead of going back to sleep, Len started rubbing his hand across my nipples. The contact thrilled me, but I forced myself to pretend to be asleep. Len slowly caressed each nipple, then moved his hand down my body. I was almost shaking with pleasure when his fingers reached my crotch. Despite my best efforts, I let out a gasp when his hand wrapped around my cock and started slowly pumping. When he heard my gasp, he quickly removed his hand and started pulling away from me. I caught his hand with mine and guided him back to my penis. He leaned into me and whispered in my ear. "Are you sure you want this?". I answered him by groaning and pumping my hips so my cock thrust in and out of his fingers. The pumping had an added effect of slipping his hard cock up and down my crack. He pushed forward at the same time I was pumping back and we managed (I think totally by accident) with the tip of his cock pressing against my butt hole. He groaned and started fisting my cock faster and I felt something wet and slippery seep from the end of his dick. He met my next push with one of his own and I felt is cock slip into my virgin ass. I froze and started whimpering as I felt the strange sensation of his cock inside me. Len groaned and started pumping my cock. At the same time he started pushing against me steadily. I was so intoxicated with the pleasure his hand was providing me, I didn't notice his cock was sinking deeper and deeper into me until I felt his wiry pubic hairs mash against my butt. Once in, he paused for me to get used to his cock in my rear and asked me if I was doing OK. I told him it felt strange. He asked me if it hurt, and I replied that it did a little at first, but now I just felt full, like I needed to use the bathroom. Len replied that it would feel a lot better in a few moments and started to slowly pull his cock out. When only the tip of is cock was left in me, he reversed direction and started pushing it back in. All the while he was working my cock like a pro. Len continued his slow fuck for the next 10 to 15 minutes. Slowly easing his cock in and out of my ass. All the while he kept stroking my cock and whispering in my ear how about how good it felt, and how hot/tight my ass was. After about the first 2 minutes of this, the "full" feeling disappeared and my ass started feeling warm. At the 5 minute mark, it started feeling HOT, and by 10 minutes, I was gasping for breath and silently begging him to fuck me harder. All the while, Len kept pounding my dick and running his hands all over my body. After about 15 minutes of this, I could take no more. My cock grew steel hard in his hand and I launched into the biggest, most intense orgasm of my life. It seemed like I came forever. I even think I passed out as my senses were overloaded. When I returned to conscious Len was still pounding away at my ass, and my cock was still rock hard. He was pumping faster, and harder. He was taking short fast strokes. It only took about 1 to 2 more minutes before he blasted his load up my ass. The instant his hot cum started burning my ass, I came again. Not a powerful, or as mind blowing as the last time, but still it was very pleasurable and completely relaxing. As Len finished his orgasm and his cock shrank, we both slipped back to sleep. My last memory of that night was his cock, now semi-soft slipping from my stretched hole. I awoke the next morning to find Len still snuggled up against me, in the same "spoons" position we were in the night before. I felt his cock pressing against my ass, but it wasn't hard. I ran my hand down, over my ass and stuck a finger inside. I felt the remains of last nights encounter and sprung an immediate erection. I reached over and started playing with Len's cock. I was trying to wake him up and get him hard at the same time. His cock came up before he woke up and ever the eager beaver, I quickly backed up to him and inserted his cock up my ass. Unfortunately, I went to fast and instead of the pleasure I felt last night, my ass felt like it was being torn open. I was unable to keep myself from crying out, and I jerked my ass off his cock. I was quietly sobbing and rubbing my ass when I felt Len's hand pull me to him. He reached around and started rubbing my cock and quietly whispered into my ear "Next time, wait for me and it won't hurt. I'd never do anything to hurt you." I turned over and looked at him. He was grinning from ear to ear. He hugged me and then told me that we didn't have time to do anything that morning and that I should probably let my ass rest for a bit anyway. We both got out of bed and I pulled on my briefs and he pulled on a pair of sweat pants. I went to the kitchen while he went to the bathroom to take a shower. When I got to the kitchen Mom made me big bowl of cereal. When Len came out of the shower, and walked into the kitchen, Mom asked him if I was a "good boy" last night. He winked at me, and told her that squirmed around a lot, but other than that I was OK. What happened after: Mom and Tony never did figure out what Len and I were doing. Every time they would go out, Len and I would go back to his room and he would screw me. He was always kind and considerate. However, he never did let me do him, and to be honest, the thought didn't occur to me. Len always gave me a "reach around" and never came before I did. We didn't kiss much, but we did hug a lot. I never slept in his bed unless there was a party but when I did, Len often left the party early and spent the night with me, holding me, loving me, and making love to me. Len got out of the Air Force about 8 months later. He moved back home to Ohio and I never saw him again. He did call four or five times, but since Mom was always around, we couldn't really say much. If you enjoyed this story, please e-mail me at firstname.lastname@example.org. As always, comments, and suggestions are welcome and will get you a reply. Flames will be deleted. If you enjoyed this story and want to read more about my life, let me know. I still haven't told you about my experiences with: the friend Len set me up with when he got out, my grandfather, my uncle, my other uncle, the high school principal, and others too numerous to think about right now... Again, you can contact me via email at email@example.com. Suggestions and critiques will be replied to, Flames will be deleted.