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I had turned eighteen and was pretty proud of myself to reach adulthood, except for one minor problem. I was still a virgin! I guess all the video games and other crap I grew up afraid of girls. I am not horrible ugly and I have a nice cock, eight inches and can blow a giant wad across the room with a good heavy load to follow. I just can not close the deal with a girl. I had one girl give me a hand job and I got jizz on her shirt which made her plenty pissed.
I finally became so desperate I even begged my mom to let me nut in her just one time, just to get me over the hump. I thought she might do it but then she said I should craiglist. She even sat down with me and went through some of the postings. I told her it would be much easier if she would just give in, it would only take a couple of minutes. Mom insisted that I try this first and if it fails maybe she would. We found an ad that mom liked, "57 year old woman looking for supplement to husband. No games, condoms a must, no drama, I have a nice body you should too." I told mom she was too old, then mom said that she was too.
I sent an email and waited hoping to get no reply so that I could finally bust one my mom. Then I got a response and was to meet her at the coffee shop. Her name was Linda and we had sent pictures so we knew who we were looking for. She looked alot like my mom, curly dark hair with some gray, bigger tits, a tad chubby and about five foot two. She did not look like a someone who would like sex at all. We met and Linda told me her story, how her husband does not do it for her anymore, just sticks it in and nuts in a few seconds maybe once a month. She was just looking for a nice guy to do stuff with and to fuck her brains out-her words honest. She said she had over two hundred responses to her ad, most were cock pics. She said she had three she liked and mine caught her eye because I was so young.
I told her my story, being honest as I was hoping things would not work out so I could bang mom. Linda and I had a nice time. For the next two weeks we talked on the phone and texted each other and had lunch. She was a really nice lady and I liked her. She seemed to be in no hurry.
Then finally she set a dinner date. We met downtown and went out to dinner and did a little shopping then went to a nice hotel where she had booked a room ahead of time. We went in and everything felt comfortable and good. We made out and then Linda said she would be right back and that I should get undressed. I took off my clothes and sat o nthe bed, Linda came out of the bathroom naked. She was not bad looking, nice tits, a little belly and a chubby little hairy pussy. She sat on the bed and we kissed, then she started crying.
Fuck me running I thought to myself. I get this close. Well Linda unloaded on me about how she fucked the first guy because he told her everything she wanted to hear, and when they fucked the condom broke and he came in her then when they were done he told her she was not what he was looking for and left her there all alone. Then the second guy spent the night with her and she thought they had a great time but after he left the next morning he texted her that he was married and this would not work for him. So now she was here with me but I was young and everybody is only looking for a quick fuck. Linda said she had only been with like four guys in her life and she did not want to be a slut. I told her to wait and what about no drama? I decided we were not going to have sex and we continued to drink wine and talk about her for another two hours naked.
We got sleepy and decided to get under the covers. Linda asked me to hold her which I did. Holding her with her naked body right caused my pecker to harden. Linda noted this and we started to kiss. After some kissing Linda climbed on top of me and lowered herself down on my cock. I watched as my virgin cock disappeared into Linda's chubby hairy wet snatch. Her pussy felt better than I expected and she fucked me real good. I did not last too long and busted a huge load deep inside her. She came at the same time I did and collasped next to me. I awoke a few hours later with Linda still asleep, the covers were all kicked off the bed and I had a great view of her cute little pussy. It was still creamy and wet and wide open so I moved in and mounted her again this time fucking her for much longer before nutting deep in her. She smiled big as the last of my jizz drained in her.
We stayed in the hotel room for the rest of the weekend and fucked. We fucked every which way, She even let me nut in her ass. She swallowed a few loads and taught me to eat pussy. Cream on her face and tits, she was like a porn star. She even wants to do a three way-both FFM and MMF. And all this in a little woman that looks like she is a prim and proper goody goody.
Well Linda and I have been fucking weekly for some time now and yes I got over the hump. With Linda's help I learned what I need to know to get into a woman's pants and have fucked many other women. I am still working on my mom, I think I may be writing a story about boning her very soon!

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05.10.2021
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Chris just said ‘now it’s your turn’. She was smiling big like she had something up her sleeve. *** Part2 Chris got up on her knees and straddled my legs. She leaned forward and planted the longest kiss I think I ever had. I kept flashing in my mind back to the wife and how this would really piss her off to know I had succumbed to the daughter’s allurer. I guess it didn’t affect me that much as I kissed her right back. As our kiss continued my hands were taking in the soft flesh of her...

Setting up Lucy2

Lucy's tongue lightly twirled on the woman’s thigh only inches away from her ultimate target. She had tasted a woman’s pussy only once before many years ago. She hadn't particularly cared for it then but now found herself anticipating the nectar that awaited her. The woman had her skirt bunched around her waist, her hands holding tightly to the table she was sitting on. As soon as Lucy's tongue made contact with the extended head of her clitoris one of her hands came behind Lucy's head...

Going out a little messy

Introduction: Getting her to take things a little farther Our life had not been the same since Lyndas time with her new lover. She was a bit more confident, well hell….a lot more confident and she seemed to be floating around with a much more positive attitude. To tell the truth I think she never thought she could have someone as hunky as Joe seeing that she was a bbw housewife with 2 kids. She finally had allowed herself to open up the sexual being inside her that her upbringing had made her...

The Balance Ch 2526

Hello Friends: Well, this tale is almost over. Only one section to go. As always, I welcome your comments and votes. ***** Chapter 25 Angela gave a startled squawk of shock and surprise. She scrambled over Abiron’s body, seeking to put him between her and the High Priestess’ wrath. Trembling, she raised herself on one elbow so she could look over Abiron’s shoulder. ‘Hello, Mother,’ Abiron’s voice was…amused? ‘It is polite to knock.’ ‘So it would have been, had these not been my own...

Americas Next top Sissy part 5

Part 5 So Part 5 of my homage to 'America's Next Top Model' forced fem style lol ... hope you enjoy it and please comment. After a humiliating photo shoot the sissies wake up to another elimination. Jim felt better after a night's sleep, only to face wearing the overly feminine pink sissy dress he and the other sissies are forced to wear for the elimination. 'Getting eliminated, maybe that's the way out? At the very least I would get the satisfaction of denying these sick...

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