When i was in the service, i used to sleep in my shorts. NOW'DAYS...i sleep nude...but...i'm not in the service, lol. i shared a room with another guy, and one night while i was asleep, he came over to my bed, and put his hand under my blanket, and started rubbing my leg...ever so gently. i was asleep, but after a bit, i woke up, and i turned over onto my belly. He was turning me on...and i didn't want him to see that, i figured he'd stop. I wasn't thinking beyond him not seeing my growing erection. But, he kept rubbing my leg...up high close to my butt. The bad thing about baggy boxers is a hand can easily slip up into them. And he slipped his hand up into my boxers...and began massaging my ass. The bad thing is, i let him...and i spread my legs a bit...which must've signaled him to continue or to go on. Well...i was getting really turned on...and he continued moving his hand closer to where he wanted to go. And i didn't stop him.
Y'know...at the time, i had NO idea what to do...let him continue, and hope he doesn't turn me in...or stop him and just let the whole thing go...i was young...and wanted it to go on...it was just him and i there...nobody would have been any the wiser. i spread my legs just a bit further...and kinda arched my back a bit.
Looking back on that night...no harm was done...he played with my ass...and he KNEW i gave him permission...after a bit...he stopped and went back to his bed. i never said anything...he never said anything. Two nights later...the same thing happened...i was on my back...he started feeling, and i rolled over. He continued...when i told him to stop, he said...NO...relax. And i did...he took his hand away...and uncovered me...and pulled my boxers down, and off...he spread my legs some...and went back to playing with my ass...with both hands...he had lube on his fingers...and i felt them enter me...omg...it was unreal...then i realized...he was masturbating. Eventually he ejaculated on my ass...and rubbed it around while i raised my ass...loving his hands on me.
THIS went on for a few weeks til he got the nerve to go further...we never spoke about it during the day...all the times i tried to talk to him about it...he ignored me. Walked away...he KNEW i had a girl friend, and we were going to get married...ha...so did i actually...but i couldn't stop it...at all...any of it. The times i WEAKLY told him to stop...he told me to relax.
I don't have any remorse over what took place...but i would've liked MORE...he seemed as though he couldn't accept any of it...like he was...detached. The only thing he ever said to me about it was one night...he asked me if i wanted him to go further, and i said yes...but...at that time i didn't realize what further was...i thought he was going to jerk me off or something. It was more intense than that. NOTHING happened for a few days, then he invited me to go out to get a few drinks with him. My gosh, i was literally just a kid, he was a bit older...but that guy could drink. I was sloshed and we went back to the barracks...and went to bed...that night i barely woke up as he removed my boxers...and told me to roll onto my belly. He didn't waste any time massaging my ass...and getting me totally turned on...made me spread my legs apart and raise my ass. And he said...that's it...as i felt him rubbing himself on me and pressure...and a considerable amount of pain...but i didn't seem to mind, but i DID mind...OMG..IT WAS INTENSE. And he stopped...his cock was inside me, i thought i could feel it, and he just lay there on top of me for a LONG time...and i began to enjoy the feel of it there. After a bit i felt him moving...he put more lube on me...and himself...and he started moving...omg...it hurt some, but i liked it...and didn't like it...but i wanted it. And he continued...he asked me if he should stop, and i said no. The whole time he was talking to me, how tight i am, how he loved it...oh yeah...etc. Eventually he got off...and went to bed. For me it was somewhat anticlimactic i wanted to cum...i was into it...he shot his load...and went to bed...this sucked. i didn't jerk off, i just covered up, and went to sleep. i really felt like...WTF. The next day i confronted him with the whole thing...he got pissed at me...called me a kid, and bullshit...telling me not to tell anybody i was just as deeply involved as he was. i had no intentions on telling anybody...even if it was the very first time...but i wanted him to get me off or help me get off...he just got pissed off, and never came over to my bed again. Which really sucked because...i wanted it again...i wanted more.