Robbie Loses His Virginity

Recently I had my first experience, and I am both amazed and confused as well as excited for it to happen again. Putting what happened to me on here was something I wanted to share with others. My name is Robbie, I am just 18 years old and out of high school graduating in the year of Covid. I am only 5'1", 130 lbs. so a little overweight. I have shoulder length light brown hair, brown eyes, and pale complexion. Because of my size, having boy boobs since I was a teenager and a small penis 4 inches when excited, high school showers after gym were so much fun. I tried to get into and out of the shower as fast as I could.

From my description and being somewhat shy I spent most of the high school time with few friends. My experiences with girls were kissing one girl once and making out with another. The second girl we were getting hot and heavy, and she reached between legs over my jeans to rub my penis. She started to giggle because how small it was. You talk about a mood killer. She tried to jerk me but well just didn't react after being laughed at. Of course, high school girls don't gossip.

It's a Friday night in December 2021, my parents are divorced, and my mom works the overnight shift so have a lot of time to myself. I went to the mall to mostly look around and must not been paying attention when I bumped into this older guy. He was well dressed and tall. I was embarrassed being so clumsy I apologized a lot. He was so nice said it was partially his fault. Walking out went to the food court and sat down and had a Pepsi when he came up smiled and asked if it was ok to sit down next to me since the food court was crowded. He introduced himself as Mark. We talked he was cool I felt so comfortable. I finished my drink and said good night and went to the bus stop for the ride home.

Standing at the bus stop and a very nice Cadillac Escalade pulled up with Mark driving. He asked me where I was going and said oh great, I live around there. Don't know if i was being naive or that liked talking with Mark but i took a chance and got in. On the way to my house in small talk i was hopping to watch rest of a hockey game he said cool so am I. Then after minute he said I have a nice tv if you want to watch it at my place and have a few beers that could be fun. Thinking for a minute and again being naive. I said sure let's stop.

His house was out of the way from mine, it was large and nice, we walked from the garage to his house. It had an open area with an incredible set of steps leading up to the second floor, but we went to his living room. There was a huge tv and incredible living room. He pointed to the couch, and I sat down, and he asked me what type of beer I wanted. What did I know I never drank anything I said whatever you have? He came back handed me the beer and sat on the other end of the couch. We talked and I finish my first beer he looked at me smiled said never had before? I smiled and said no. He said let me get you another one. Only this time when he came back, he sat next to me. I sort noticed but thought the action in the game was getting good it was near the end. Then he starts touching me to point out something in the game. I was getting a little nervous but still felt ok a nice guy just enthusiastic.

Somewhere halfway through the second beer he put his hands on my shoulders and said wow you sat to far forward your back is tight. He started massaging my shoulders. I froze finally i figured out what was going on here. I didn't know what to do, run, try to push him off me or what. I just went along with it as i was really frozen at one point he found a tight spot in my back and i made the mistake of sighing. He moved his head closer and started kissing my neck and shoulder. I was even more scared but also shivering from the kisses as he much has found an area that was sensitive.

He worked my polo shirt over my head, and I was in a trance maybe the almost 2 beers, the fear or just being that close with someone i just went along. He then started kissing down my shoulders his one hand worked my right nipple while his mouth dropped to my left nipple. He licked sucked and even bit a little on my left breast. I started to moan out loud when I did, he pulled his face back looked into my eyes and said you have great tits. Hearing that I cannot tell you how much I was embarrassed. Girls have tits i am a boy.

He just dropped his head back down on my tits and kept leaning into me till i was laying back on the couch with his body somewhat on mine. He then kissed up to my lips and locked his lips on mine at first i didn't do anything he learned back and said ahhh a little shy that is cute. He went back to work and then his tongue forced its way into my mouth. His tongue invaded my mouth it was forceful and strong. Laying back I am thinking oh my god when i made out with one girl my tongue was in her mouth. I started to realize I was a girl with tits and a man's tongue taking my mouth. Sometime while his tongue was in my mouth, he had pulled both my pants and boxers off my lower body. To my surprise it just dawned on my penis was hard and ever. As he bent down to take my socks off i realize holy hell, I am freaking naked on a guy's couch who is kissing me. Mark was still dressed at this time. Embarrassed and waiting for a joke about my penis size he just looked at me and said your penis is so cute. Down went his head and he started licking both my penis and balls. His mouth opened and without much effort took my whole penis in his mouth. While doing that, the first time ever I felt something in my buns his finger. I knew I was going to come and tried to warn him, but he didn't stop and when i exploded the most i ever have he just swallowed it all. After what seemed like forever I was finished. He started kissing up my stomach and then kissed me on the lips and of course with his tongue in my mouth for a few minutes.

He stood up off the couch as i laid catching my breath he stood up unbuttoned his cuffs on his dress shirt and motioned for me to help. I got up and opened his buttons and helped his shirt off and his tee shirt also. I licked his nipples some. He stopped me and said your mom is working late so you don't have a curfew. Being shy and my head spinning i just muttered yes, i guess. He smiled put out his hand to mine and said come on Roberta we are going upstairs. I went to grab my clothes, but he playfully slapped my buns and said you won't need them boy.

He put his arms around me and walked me to the steps and we slowly went up to the first landing at this point his hand slipped from around my back and down to my buns. He stopped on the first landing to make out some as he felt my buns and told me you have the most gorgeous bubble butt. I had no idea what that meant but notice I was like all weak like i wanted to hear that. While we made out, he did move my hands to the front his pants and I rubbed his penis. It was large I could tell. We broke form kissing and made it the top of the stairs and he points to a large room and said oh that is my bedroom, but we are going to my "fun" room.

We walked into his fun room it was dark but had a large bed in the middle of the room with chairs against the wall around all sides of the bed. There were a lot of mirrors on all the walls. At the top of the bed there were two nightstands each had a laptop type computer on them. He had me sit on one side of the bed and told me to relax. He went over played with the computers a lot of lights overhead came on and the room come alive. He turned and said I like seeing what is going on.

He walked over in front of me and put his large hands on my shoulder and convinced me to get off the bed to my knees. I opened his belt and zipper lowered his pants and silk underwear as I looked ahead a second, I seen the largest penis I have ever seen. It bumped into my face. Before I could do anything, he said get my pants all the way off and my socks. I did. I noticed his tone was a little more excited or forceful. When I finished with his socks, he said thank you Roberta honey. I was right I thought to myself he did call me Roberta before. I looked up from my knees and said my name is Robbie and he chuckled and said not for long. He then rubbed his penis on my face I knew what he wanted. I told him I was afraid I could not get that penis in my mouth it was so big. He said honey that is not a penis that is a cock. Oh, confused I said you used the penis word for mine. He chuckled again and said yeah that is a penis you have. This big it is a cock. I was blushing from his comment he said oh you look so cute blushing, but you would looked better with a cock in your mouth. Taking the hint, I leaned forward and worked opening my mouth to get his cock in. It was at least nine inches long and maybe 5 inches around. I worked at it gagged a little but after a while got a good bit in till he started pushing his hips forward. I thought i was going to choke but then he stopped pulled it out.

He lifted me off the floor on to the bed and started kissing my penis and balls again. I was hard again after a minute or so of these he turned me over. Then he buried his face between my bun cheeks and for the first time I felt a tongue in what my religious mom refers to as the dirty hole. I felt his large hands pull my cheeks apart as his tongue worked into me. The was incredible I was moaning and pumping my ass back to meet his tongue. He rubbed my balls some and kept his tongue in me for a long time. My penis was so hard it hurt.

He then left my backside and started kissing my lower back work his way slowly up to my shoulders. As he did this, I could feel his large cock working up my legs to my ass. I was scared and trembling. I told him I did not think i was ready to make love. He leaned in and said don't worry Roberta we are not making love I am going fuck you. And you are going to become Roberta. He said trust me your boy pussy is ready. He pulled me up on my knees and hands and told me to look into the mirror to watch it. I was so scared I was shaking. Looking at the mirror it was like watching a porn video on my friend's computer. It was also like watching someone else.

I could feel his cock head position at the entrance of my boy pussy then slowly he worked the head in. I was hurting and scared and crying but he kept one hand on my hip and other stroking my back as he worked his cock in. It hurt a lot he leaned in and told to pretend I was going to bathroom and push my pussy. I did and after a few long seconds his cock seemed get pass something and the pain was going away. I got into a rhythm with him as he grunted that's it bitch get into it. That b word made me more embarrassed and excited not even sure if that makes sense. He was fucking me hard, and I looked into the mirror at the bitch who was moaning and telling him fuck me harder please. At one point I looked at the mirror on the side wall near the bed and could see the length of his cock entering my pussy.

He kept shifting different levels like riding high on me. Then it dawned on me I asked him between moans when he pulls out to come on my ass if he would want me to suck him. He said no bitch I am going to breed you in your boy pussy. I am going to explode with cum into your very tight pussy. I came at that moment without touching my penis. Come was gushing out of my penis. Then he angled a little higher i lowered my head the pace was fast and hard, i could feel his balls bouncing on me and hard slapping of the skin. Then it happened he groaned as my face was buried in the mattress, I begged for him to fill me even shouting breed me. He came, wow did he come i felt it, my penis was bouncing i don't think I went soft after coming. Near the end he pulled the hair on the back of my head and said look Roberta in the mirror you are now my bitch. I fucking own you. You pussy is mine. I gave out a look of realization what i have become. He rolled off me on the bed to catch his breath. I stayed fixated on all fours looking into mirror crying some realizing I did lose my virginity but not how i thought. I then collapsed onto the mattress also.

After a few minutes I don't why he had me get up sit on my buns and moved me to the center of the bed. We just started talking about what happen. He asked me a lot of questions about my name, what school i had went to. How i just lived with my mom. He told me he thought it was cute i didn't use slang words at first. Told him was because my mom is so religious. Then he asked about my sex life and had I ever even thought about guys. Of course, he called me Roberta the whole time. He had me get on all fours turn completely around on the bed and he opened my buns to look at my boy pussy hole. After that he turned off the computers and turned the lights down some. We talked longer about different things and he told me about himself he was 37 gay and traveled a lot for business. Then he said he was having a holiday party with his friends in a few weeks did i want to come to it.

Seeing it was 3 AM at this point we had been at all this for over 4 hours he told me let's get you home. We went downstairs I was in front of him he told me shake that ass Roberta remember you're a cock slut now. We got to the couch he got his wallet gave me 20 dollars said I am keeping your boxers here replace them with a nice set of panties.

We got to the car and drove to my house. He pulled up two houses before mine it was a lot darker there. As we stopped, he kissed me and said oh Roberta. I looked down his zipper was open his cock are hard again and without asking I dropped my head and sucked him till he came in my mouth. Strangely felt proud about doing that.

I got out of his car and walked to my house and went in and went to sleep naked in my bed. Now all I can think about is the party with his friends.