As a teen and into my 20s I had a very nice body everyone told me. Everyone called me pretty, boyfriends told me I was beautiful. I was 20 and in college before I let a guy feel my tits. I let him do it under my shirt and without my bra. Eventually I even opened my blouse and would let him feel them while we kissed. Then out of nowhere he just stopped dating me. I tried to get him back again but to no avail. The next guy was at my first job. I wouldn’t date anyone I worked with so it was someone I met through a friend. We dated for a few months and I did let him see and feel and suck my boobs, he was the first one whose penis I saw and touched. I rubbed a couple through their pants, but his I saw and started using my hand on him so he could have some relief. He liked to cum on my boobs, which are pretty large, I was a 34DD at the time. He wanted me to lick it off my boobs and I just couldn’t do it. His threats to leave me made me do it. To tell the truth it was arousing, I masturbated at home after, but the taste left something to be desired.
He kept wanting to feel me between the legs, and I wouldn’t let him, then finally let him under my skirt but wouldn’t take my panties off. He did put his hand through the leg hole of my panties to rub me down there. He felt all my hair down that and started chuckling. “I didn’t think anyone keeps a hairy cunt anymore” he said “I’ve got to see it” he added. I told him no, but he pushed me over in the car seat and lifted my skirt anyway. I was trying to push it down as he grabbed the top of my panties. He pulled them down in front so he could see. “Holy shit that’s a lot of hair, haven’t you ever trimmed it or shaved it?”. I slapped him and got out of the car headed in to my house. He tried to follow me, turning me around on the walkway to my door. “If you don’t stop I’m going to yell RAPE” I told him. He immediately turned around calling me a fridged, fucking cunt on his way to his car.
So, through my late 20s I was alone only with girlfriends, nothing lesbian or anything. I gradually put on weight, and don’t feel I’m too appealing anymore. I realize that I missed out on so much. I’m a 37 year old, very chubby virgin. I did some online attempts through apps, 3 of the men I was interested in stopped everything, wouldn’t even chat with me because I told them I was a virgin. I had 6 others who all of a sudden started only talking about fucking, and having sex. Telling me they could take me to new heights and every other euphemism possible.
I am used to not having a love relationship, I can do without that, but I want to know what sex is like. To tell the truth I’m scared shitless of that first thrust into me. I just don’t know how much it will hurt. My hymen is intact and I am afraid of the pain. Also men all seem to want blowjobs, and I remember I didn’t like licking that guys sperm off my boobs.
I’m thinking about going on a vacation on my own, telling no one, and maybe hiring a nice, older escort or something to do the deed and stay with me for a few days having sex.
I really feel left out. When girlfriends talk about sex, I just go along and pretend with them. It’s weird I don’t think I want a relationship, but don’t want to be a slut either. But either way I have to get through this first. I’m scared and hate that I have to resort to maybe paying an escort to romance me into sex.
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