Guy time

Guy time
I was just about twenty years old when I wanted to give another go with guys. I had no girlfriend and found myself questioning my sexuality since I was obsessed with gay porn. I had been experimenting with anal beads, dildos, and sounding. I lived in a two bedroom apartment and my roommate was gone for the summer. We didn’t have AC so I usually was naked inside my apartment.

I jerked off several times a day to gay videos and porn. I created several gay profiles and posted hundreds of pictures and videos of myself using my toys. Before long, it consumed my day interacting with several unknown men. My audience seemed made up of guys in their mid thirties to early fifties. With guys, it seemed the ones that wanted to hook up always needed a place to play. So my apartment was a perfect meeting place. I wasn’t scared about meeting guys from online either. I wanted to be viewed and treated like a piece of meat. Within days of online play, I had my first encounter.

I’m just going to say guy #1, because he didn’t share his real name with me. Guy 1 and I had only known each other a few days. We did the typical exchange of of faceless nudes, dirty talk of what he wanted to do with me and I with him. We had scripted our meeting prior to him coming to my apartment late one evening. Guy 1, was 34, single, black, 5’9″, 225lbs, hung (9 inches),cut, top. I was 19, white, skinny 165lbs, 5’11” , average (just under 7 inches), cut, bottom. Which seemed a perfect match. He had asked that I wear a pair of custom jeans had cut into assless chaps. I wanted to be spanked as soon as he arrived, taking me over his knees as punishment for being such a bad boy. Guy 1 showed up. He grabbed my cock as he entered. I can still recall how he smelled of smoke. He sat in a chair I placed in the middle of the room. I bent over his lap and he began to hammer my pale white cheeks with his strong hand. He asked me if I was bad between his punishment. His spanks got harder. My ass was throbbing and tears swelled up in my eyes. It got to be painful and I succumbed to begging for him to stop. I stood up and admired his work in the long mirror placed against the wall. Guy 1 stood up and unbuckled his pants. I got on my knees sideways in front of the mirror. I pulled his massive meat middle and wrapped my mouth around it. It was thicker than my dildo I had practiced on. My jaw made a popping sound as I opened wider for him. I worked both hands on his shaft while I struggled to get an inch past his tip. He talked non stop about what a good bitch I was. I gagged a few times almost throwing up. I knew I had to relax my throat if I was to keep my end of the deal, I had told him I could swallow his entire cock. I blocked his talking out and closed my eyes. He kept putting his hands on my head. I finally had to ask him to stop so I could focus. He even quieted down. I had gotten used to his gerth and felt him slide down into my throat. I made the mistake of looking into the mirror and it caused me to panic a little. I couldn’t get him out quick enough and spit up onto the floor. I had some strawberry scented lube and put a glaze over his tip and shaft. I went for broke and forced my head up to his pubic hairs. They tickled my nose and I pulled back. Then I did it again and again, holding a little longer. Luckily his cock wasn’t really hard and I could manipulate it down into my throat. I made some nasty gurgling sounds as his cock traveled deep in and out my throat. I was close and reached my hands around him and pulled myself hard. The strawberry scented lube filled my nasal passages and I couldn’t breathe. Saliva was dripping uncontrollably out the sides of my mouth. My jaw was sore from opening but I had finally buried my face into him. I backed off, I was sweating profusely and took long deep breathes just to fill my lungs. I began to suck more and harder, not going all the way but far enough. I put my hands on my thighs sitting up on my knees. I just held my mouth open as drool splattered over my hands and legs while he pumped into me with his hands firmly on the top of my head. I was getting tired and closed my eyes hoping he would end it. He kept going and going. My jaw ached, the pain my ass was being trumped by the jaw pain. He pulled me in hard. His cum filled my mouth, I gagged and choked on it. I jerked back and accidentally bit down on him. He shoved me off pushing me over. I swallowed hard on his salty cum. He was rubbing a few squirts of cum out and I went over to pick up the leftovers. I sucked him dry. He pulled his pants up and left without saying a word. I never heard from him again. I saw him online but he never messaged me back. I had felt hurt initially but then came to appreciate the “wham bam thank you mam” approach he took with me.

Guy 2 was much different. He was 44, slender swimmers build, wore glasses, 5’7″, 7.5 inches, cut, thin cock, 165lbs. He wanted just one huge thing… bareback cum in ass. The other thing is he wanted me to crossdresser as a school girl. He lived in a trailer park only a few minutes away. I gave him my measurements prior to going over to his place. It was a Monday afternoon when I drove to his trailer. He welcomed me in, we shook hands while introducing ourselves and he seemed very happy to see me. I quickly noticed the video camera and lights in his living room area. He showed me to the back bedroom where the clothes he had purchased for me were placed neatly on the bed. He went back to the living room for me to change. I had never worn stockings before and my toe nails kept getting snagged. I put on the grey plaid skirt and white top. While I was getting dressed. Someone else arrived. To my shock it was a woman’s voice I heard. He led her back to me. I felt a little awkward being dressed like a school girl in front of her. She introduced herself. She had a large make-up case and purse. I was told she was to help me get ready. Guy 2 left us. She was very chatty asking me all sorts of things while she put eye shadow, blush and lip stick. I sat looking into the mirror as she transformed me. She then pulled out a long brown wig and pinned it in place. As we talked she let it be know that guy 2 was actually her husband and that the trailer was their “sex shack”. She also told me that she’d be the one filming us. After she finished getting me ready, she asked if I looked good enough to fuck myself. Amazing, yes I did. I felt pretty awesome, I felt feminine, and sexy. We went to the living room and he was laying on the couch naked.
I sat on the couch next to him, Guy 2 sat up. We started fondling each other. He groped my chest and we kissed. He then got on his knees and sucked my cock. I was impressed how passionate he was with me. His hands flowed over my body. Under my white top, under my skirt. He lifted my legs up, as she got a close up of me. He rimmed my ass,poking his finger into me. He opened me up by putting both first fingers into me stretching me apart. It was uncomfortable to say the least. We went to the floor. I was on all fours. Guy 2 was behind me with my skirt pulled up. He rubbed himself until hard. He spit into my ass rubbing in. Then he rubbed his cock up against me. I forgot about his wife and just gave into the moment. I wanted to be that girl for him. I moaned softly as he entered into my backside. He leaned over me and I turned my head back around to give him a kiss but I wasn’t flexible enough. Instead, in a high pitched voice, I asked him to fuck me. His eyes lit up and even his wife said yes! He took me from behind, then I rode him on the floor, then cowgirl, then finally with me on my back. My legs pushed up over my head. Guy unloaded into my ass. His cum was most welcome inside me. After his deposited his full load, he kept my legs pinned up to watch his cum ooze out of my ass. I felt it drain down the crack of my cheeks. We finished. I was given a towel to clean up. Guy 2 and his wife were very satisfied with me. I enjoyed being dressed up and told them. I got to keep the clothes and wig in return for not sharing what took place and a copy of the video. The experience had me wanting more.