This is a true story; If you are not 21 or over do not go any further. If you do not like man on man sex go no further.
Note: This segment of the story is a step backward in time. Several of you have written me asking that I go back and expand on my college experiences, which I'm happy to do.
Going back to the end of Part 9...
"Thank you Tommy" and I reached up to kiss him lightly on the cheek. I reached one arm around him and we hugged clumsily and I let out a sob. I felt his cum sliding down my leg and somehow wanted more, wanted to do more with this man, for this man. He knew I was a guy and he still wanted to treat me like a woman. Even now, after he had shot his load and could leave, he was being nice to me and apologizing. Maybe because he knew he should, but also maybe because he wanted to see me again, that he had a need to get laid and wanted my body to please him again.
As we separated I knew it was only a matter of time before I called him up, asking for sex.
Tommy left my room, closing the door behind him. In a fog I walked into my bathroom and sat on the toilet, expelling as much as possible and wiping my bottom carefully. I felt my hole with my fingers and was glad not to feel anything wrong, but I sat there confused, remembering how much pain his cock had given me. I realized that I had made a mistake - thinking that Tommy's smaller, thinner cock would not be a problem for me, relying on the fact that I had had Howard's longer thicker cock and larger objects into me previously. I knew then that I'd need to be more attentive - before I gave my bottom to a man that I would always need to lube and loosen it, regardless of the cock size.
I also knew that even though the sex was painful, while it was happening I loved it, really wanted it and didn't want to stop it, even if I could. It was so sexy for me. Tommy's surprising strength and wild thrusting, the way he dominated me was such a turn on that as I sat there my small cock began to harden. I stroked myself thinking about how good it felt to be held from behind, our bodies slapping, my ass cheeks rippling with each quick jab of his groin. His final deep thrusts - the feeling of his wiry pubic hair pressed into my smooth bottom, his wheezing breath on my neck.
I stood in front of the vanity, looking at myself in the mirror - pleased with the beautiful 'girl' I saw - and continued stroking my cock which had now grown to its full length, slightly longer than the width of my palm. I quickly found the rose scented bath oil and used a little in my palm, treating myself to a soft, sensual milking grip. I relived the experience of being fucked while standing, imagining that this time Tommy held my cock, pleasing me as he used my bottom. I milked several long squirts of cum into my hand, and closed my eyes, enjoying the release.
As I caught my breath I considered that this was the best release I had every had. I lifted the small pool of whitish goo to my mouth and licked my palm, slowly letting it slide into my mouth, tasting and swallowing.
After I cleaned up I went to my bed, peeled back the blankets, removed the belt and blouse I was still wearing, and slipped into bed. I was tired and wanted to rest. I wanted to gather my thoughts - what would I tell Howard if he asked about Tommy? As I laid there I ran my hand over the sore spot on my rump where Tommy had spanked me. Although I didn't really like being spanked, I began to think that I knew where he was coming from - that Tommy needed compliance from me and didn't want to deal with rejection. Perhaps he had too much rejection in his life, perhaps even from his wife, and just wanted to be in control. Although he was in control, somehow he was also vulnerable and needed me to submit, to give him, or allow him to take, what he needed.
Yes - that's why he wanted me to clearly ask him to fuck me - he needed to hear me say it, to ask for it.
I certainly didn't want to get spanked again, but I also didn't want to hold this against Tommy. I knew that I had been a bit of a tease with him, and I had reason to think that Tommy wasn't getting a lot of sex at home. Howard had clearly 'given me' to Tommy and left us alone so I could please him. Tommy didn't have 'right' to hurt me, but it seemed to me like he did have a right to expect me to be a little more compliant and responsive to his sexual needs. I was starting to understand how complex this situation was.
I tried to set those thoughts in my head aside and rested a while. After about an hour I got up to get dressed, curious to see if Howard had come back yet.
I looked at myself in the full length mirror and was worried to see that the red handprint on my right cheek had darkened and was not fading away. I didn't want to make a big deal about it and knew that I'd try not to let Howard know what his friend had done to me. I searched through the bathroom hoping to find some skin-tinted women's makeup to help tone down the imprint. There was none, only the few items Howard had provided me and I was somehow happy - happy that maybe Howard didn't have a string of 'girlfriends' using this bathroom, that maybe I was the only one.
I found a fresh washcloth and ran the tap, giving my body a thorough bird-bath at the sink, followed with a quick rub down with one of the floral scented body lotions.
I returned to the bedroom and searched through the mostly empty dresser drawers reviewing the clothing items Howard had provided me. I found the crotchless fishnet body suit and thought that it might help mask the handprint. I removed the blouse and stepped into the body suit, smoothing it out over my legs and curves. I found my black panties with the feminine pad and stepped into them, making the right adjustments. I wiggled into the tight black pants, threw on the blouse and the silver chain around my waist. As I swiveled the chain clip around to rest on my hip, I though of how Tommy had held me by the chain, moving my body in position for him to fuck.
In the bathroom I refreshed my lipstick, adjusted my wig and placed a fresh dab of cologne on my neck and wrists. I slipped my feet back back into the velvet print high heels and walked out to the livingroom.
Howard was sitting on the couch watching TV and looked up, happy, his eyes a little glassy. It was late and he was still drinking beer so I wasn't sure if he was drunk or just tired. I smiled and sat next to him, wrapping an arm across his shoulders and giving him a soft kiss hello.
"Wow, I am still amazed at how great you look honey".
"Thank you Howard, for everything, you've been so nice to me"
"Is Tommy still here?"
"No, he left a little while ago" I smiled and coyly added "but he left happy".
"I'll bet he did...so what did you two do?"
I wasn't sure he wanted to know all the details, I wasn't sure I wanted him to know - I didn't know what that would do for his relationship with Tommy, or with me for that matter. I decided to avoid answering if I could. Hugging Howard I quietly said, "Oh you know, the usual stuff...but I would rather have been with you". As I listened to the words coming out of my mouth, I wondered if they were true, if I was lying to him and to myself?
He smiled, hugged me back and said "Well, I want to thank you, that was nice of you, being good for Tommy".
I sensed that he wasn't jealous and was willing to share more, so I asked "So, how do you two know each other?"
Howard explained that they were friends since their freshman year in college, that they had a few classes together even though they were following different degree tracks and they just became friends. Intrigued I decided to press for a little more info.
"What kind of friendship are we talking about...were you two..?" I didn't finish the sentence and let the question hang.
"Gay - oh no, God no...I myself didn't start until much later in life, and the professor there, he's straight as an arrow".
I thought about how Tommy knelt down and ran his tongue inside my bottom and how many people would consider that straight, but decided not to ask. Instead, I said "So, when did you, like, start to try gay things?".
"I was in my 30s, dating women once in a while, not getting anywhere, not sure what I wanted, becoming convinced that I didn't want to get married. I was horny and would go down to Times Square, to get porno in the adult shops there. It was a few years ago - things there were pretty wild."
He went on to explain that he would enter a small booth with a video screen where he could watch x-rated movies by inserting coins or tokens into the wall. There was a selection of movies and he found himself enjoying the movies of men having sex with men. After a while that was the only type of movie he'd watch, and jerk off to. He said from there it was a steady progression to glory-hole sex and visiting the gay baths in New York City that were open at the time. He had to explain all of these to me - I knew nothing about them at the time - I was amazed and aroused. The thought of watching Howard walk around a bathhouse nude, grabbing a total stranger and fucking him in the locker room seemed awesome. I thought about sitting in a video booth and seeing a huge cock like Howard's press through a hole in the wall, needing to be sucked.
I was stroking Howard and his cock had tented up nicely for me. I decided to push a little further "Have you, had many guys that dress like girls?"
I was embarrassed for asking, knowing how jealous I sounded, but I wanted to know.
"No baby, you are the first. You're a real fantasy for me. I always wanted this...and you, you're a dream come true". I buried my face in his chest, hugging him.
Howard stood and pulled me up and we walked down the hall to his bedroom with Howard's hand holding my ass.
Howard kissed me deeply and then propelled me to the bed, where I sat, pulling my legs up under me. He lit a few candles and dimmed the lights and stood proudly in front of me, starting to undress.
I kicked the high heels off and slipped off the blouse, revealing the fishnet halter top underneath. Howard's eyes lit up as I stood on the floor and slowly wiggled the tight pants down, revealing the body stocking underneath, smiling back at him. I crawled onto the bed and over to his side. I quivered at the sight of his naked body, his strong arms and his massive, hairy belly. His thick cock standing straight out.
I though of how different his body was from Tommy's. I thought of how horny they both made me. I realized then that I wasn't attracted to only one body type. I raised myself on my knees and hugged him, touching him, cooing in his ear. I reached down and fondled his heavy nut sack, and gently traced my fingers along his shaft. We kissed until he could stand it no more. He gently pulled his head back and forced mine down to meet his cock.
Knowing what he wanted I immediately started sucking him, taking his head into my mouth, as I swiveled him to sit on the edge of the bed. My head bobbed up and down and I felt him moving, bucking and tasted precum in my mouth. "No no no no" he moaned quietly as he grabbed his cock tightly at the base, withdrawing it from my mouth.
He smiled down at me, almost laughing as he batted me playfully in the face with his erect cock.
"Not so fast baby, I need to put my seed into you"
I nodded OK and asked if I could first...prepare myself?
"Of course, baby, sorry I forgot..." he answered as he handed me a jar of vaseline from the nightstand drawer. I took it and walked into the bathroom, closing the door behind me.
I slipped off the panties and put a towel on the floor and kneeled down. I dug my finger into the jar and pushed a large amount of the vaseline into my bottom, pushing and wiggling it in. I didn't have anything else to use, so I worked my bottom open with only my fingers and lots of vaseline. I wanted to be moist, hot and ready for Howard so I worked four fingers into my bottom hole.
When I felt ready I stood and washed my hands thoroughly and put the panties back on. Opening the door I looked in to see Howard propped up on some pillows, his semi-soft cock laying proudly across his thigh. I walked right over the edge of the bed and bent over him, taking his cock in my mouth after whispering "Sorry I took so long".
His hand was on my ass, stroking and pulling and I was glad for the dim light, hoping he wouldn't see the bruise his friend had given me. When he was ready he instructed me to stand and remove the panties and squat on the edge of the bed, with my feet and bottom hanging over. He moved behind me and grabbed his cock by the base and started rubbing it along my crack, pushing it in. I reached back to pull one cheek aside to help him. He laughed a sinister laugh "You think I need your help to get in there baby, think I haven't done this before?"
I was a little scared with his tone of voice and quickly took my hand away and whispered back "No honey, you know what to do, you don't need my help" as I pushed out with my bottom muscles. Hoping it would help I added "Your the man here honey, take what you want from me".
He pushed in and his cockhead was quickly at my hole, pressing. His hands were tight on my hips holding me as he thrust in for his full length. "Uuugh" I gasped, feeling the pleasure of him being fully inside me. Slowly he drew his cock in and out the full length and I panted with pleasure.
"Oh, you like that baby?"
"Yes Howard, I like anything you want to do to me, you know that" I moaned.
He pushed my head down to the mattress, and switched his grip to one hip and the opposite ankle. He started thrusting, pounding, relentlessly. I was delirious, feeling my bottom being used, feeling him grunt and wheeze against me. With long final thrusts he pushed his seed deep into me, and stood there, with his cock buried in my bottom, catching his breath.
After a few moments he withdrew his cock and gently pushed me to lay flat on my stomach. He parted my legs and seemed to enjoy looking at my bottom hole, which I felt his cum dribble out of.
"Nice baby, you have a nice little pussy"
I was panting myself, happy, and exhausted. "Thank you Howard, thank you" I panted. i was amazed that Howard's large cock gave me less pain than Tommy's smaller cock and was thankful for the time I had taken to prepare.
I laid there as Howard slipped on a pair of silk boxers and climbed into the other side of the bed. Slowly I sat up and Howard told me to undress and climb into bed so we could get to sleep.
In the bathroom I stripped out of the body stocking and removed the wig. Keeping my hands in covering my pubic area I walked back into the room and slipped my panties back on. I didn't bother to tuck my small cock back, wanting to relax while we slept. I was glad for the feminine pad taped to my panties - already feeling a slippery little leakage back there.
I turned off the lights and climbed into bed with Howard, squeezing my small body against his.
End Part 11