I had my first sexual experience after one of my parents’ parties; not only was it my first time having sex, but it was also the first time that I fucked a BBW AND the first time that I was with someone with both tits AND a cock. Let me explain.
Mom and Dad often had small parties at our house, and so I was exposed to a variety of people who were usually d***k. My own mother and s****rs were skinny, but for some reason, I was always attracted to very large women.
One of their friends was a woman named Sherry; Sherry had a great sense of humor and played around with me and my s****rs a lot; we always ran to her whenever she visited our parents. She had straight, bleached-blonde hair, great make-up, and was a large woman, probably weighing about 300 lbs. She was in her forties and had still never been married (which was one of the things that mystified me about her: how could a woman be so sexy and still never have been married). After one of her visits, I usually masturbated while thinking of seeing her big tits and ass.
After one of my parents’ parties, some people spent the night and so we were putting people on the couch and on quilts on the floor. However, though I don’t remember how or why, it was decided that Sherry would sl**p with me in my bed. As soon as I heard that decision, my dick started getting hard. When I went to bed, the party was in its last throes, and I fell asl**p in bed alone, jacking off while I imagined Sherry’s naked body.
At one point, I woke up to find that Sherry was in bed with me, and, by the sound of her breathing, she seemed to be asl**p. It was a warm summer night and so we weren’t using covers. Sherry had obviously planned on spending the night because she was wearing pajamas, and she was lying on her left side with her face to the wall and her big ass in front of me. I lay there, looking at her big ass, then pulled my own pajama bottom down and began stoking my stiff dick. Emboldened by hormones, I moved closer to her and pressed my hard cock against her ass. She stirred a little bit but didn’t wake. I wrapped my arm around her full stomach, fantasizing that we were a married couple, and then I fell asl**p.
I was reawakened when a now-awake Sherry began pushing her ass back against me. While asl**p, my dick had gone limp, but it instantly sprang back with a vengeance and I returned Sherry’s thrusts, pushing my hard dick against that big, beautiful ass. I also began massaging one of her big tits and began kissing and biting her neck underneath that sexy, silky hair.
Really turned on now, I slid my hand down to the top of her bottom pajamas and was going to slide my finger into her pussy, but she grabbed my hand, stopping me. Then, she rolled over so that we were face to face.
“Is it because I’m too young.” I asked her.
“No,” she said.
“Is it because you’re friends with Mom and Dad?”
“No, definitely not,” she said.
“Sherry, you are the hottest woman I’ve ever seen,” I said. “Please fuck me.” Then Sherry leaned forward and while we kissed each other long and passionately, I began squeezing her fat ass and she began rubbing the hard bulge in my pajamas.
Then she suddenly stopped. “No, I can’t, Kyle,” she said.
I grabbed her arm. “Why not, Sherry? Is whatever it is the reason you don’t ever have a boyfriend?”
“No one would ever want to be with someone like me,” she answered, and tears were now coming from her eyes. I reached out to her and pulled her to me for a strong hug.
“Sherry, you are beautiful and funny and kind…my s****rs and I all love you…you can tell me anything and I would still want to be with you.” Then we kissed again but softly this time, gently.
“If I show you why I don’t have a boyfriend, you can’t tell anyone, okay?” Sherry pleaded.
“Of course not, Sherry.”
Then Sherry got on her knees before me and slowly pulled down her pajama and panties. I couldn’t wait to see her hairy pussy, but as she pulled the clothes down, I saw a semi-hard dick! She pulled even further and then I saw a pussy as well. Oh, my god….Sherry was a hermaphrodite! And then my dick was instantly hard! I was young and inexperienced, and I don’t know why, but I was immediately turned on by the fact that the woman in front of me, who I wanted to fuck, had both a cock and a pussy.
“Oh, my god!” I said out loud, and Sherry pulled her bottoms up.
“You see…” she began saying, then I stopped her by grasping the top of her bottoms and pulled them back down.
“Sherry,” I said, now reaching forward to grasp her dick. “I would be with you no matter what.” And I began sliding my hand up and down her cock and watched it getting hard; I was really turned on now. Other than in magazines, I had never seen another person’s cock before, and so I was very surprised by the fact that I found her big dick really exciting!
I leaned forward and began sucking her cock. “Oh, fuck, Kyle! You are the first person to ever suck my dick…that feels so good! Suck my cock! Suck it!” Just before she seemed ready to cum, I got on my knees and moved her forward, and pulled her bottoms all the way off so that she was on her hands and knees with her big ass in front of me.
“Sherry, I have wanted to see your sexy ass for so long.” Then I moved forward, sliding my young, hard dick into her wet pussy. “Stroke your dick, Sherry. Stroke it for me! I love all of you,” I said as I fucked her. “I’m going to fuck you, then I’m gonna let you fuck me!”
She began doing just that, and I leaned over so I could see her jacking herself off while I fucked her. Seeing a woman stroke her own cock and seeing my dick going in and out of a fat woman was more than I could bear and so I burst my load inside of her. “Ohhh, fuuuck! I’m cumming! I’m cumming!!!!!!!!!!!!!!!!!!!!!”
Then I pulled out and got on my own hands and knees. “Fuck me, Sherry. I love all of you, and I want you to be happy. Fuck me with your cock.” She moved behind me and spit onto my asshole. She rubbed her saliva around my asshole, and my dick started getting hard again. She spit again on her own hard dick, then moved her hips forward. The head of her cock pressed against my ass, and I f***ed myself to relax so she could slide it all the way in. I got so turned on as I felt her hard dick move all the way inside of me.
“Oh, god,” she said. “You feel so good. I’m finally fucking someone…I’m finally fucking an asshole…I’ve finally found someone to take my big, hard dick!” Sherry began fucking me harder, getting close to cumming.
“Yes!” I said. “Fuck me! Fuck that asshole! Cum inside of me!” Then she thrust hard inside of me and held it so she could cum deep inside my ass.
“Ohhhhh, fuck!!!!!” she exclaimed as she came inside me. “Ohhhhh, god damn! Oh, my fucking god, that feels so good!”
After she came, she lay down beside me and we looked into each other’s eyes. “You are perfect, Sherry,” I said, and she began tearing up again. I pulled her head toward mine and we kissed again, then we moved our bodies together and hugged each other tight.
After several minutes, we put our pajamas back on, then pressed closely together and fell asl**p.