I was out of town on biz for months. I had an apartment. I got tired of visits to the ABS and online jacking. I did meet in a chat a really nice, though quite plump (firm but plump) divorced woman of 50. We were fucking a lot, she loved it up her ass and was really good at sucking and fucking in her shaved pussy too. Her tits were huge E cups I think she said with rosy areolae and pencil eraser nipples. It was my time to experiment. I had Joy, the older woman and she even let me watch her get fucked by a guy we found. I dated a tranny at that time also. She was born male, but her testicles never dropped, so she was raised as a female. Eventually through surgery they removed the remnants of testicles in her body. She was on hormones since she was about 10 or so I think. She had really nice C cup tits. It took me weeks before I could get her to have sex. She was not wanting to be with someone who was just ticking off a mark on their bucket list. She’d been burned several times. Dee was her name and she was 5ft. 4in tall, slightly chubby, not much though she weighed 138lbs. She had a nice shape, and cute butt which I’d seen when we went to the beach a few times. Finally after dinner and theater we were in her place, having a nightcap. She excused herself and came out wearing a see through short nightie. White lace panties didn’t reveal a bulge. In bed finally I saw it. She didn’t want me to have to do anything, her little 2 inch really thin cock was sensitive but no sack no testes. It was a lot of kissing, her sucking me hard, me cumming in her mouth once, then lasted 30 minutes when in missionary I fucked her in her tranny ass.
So not for lack of sex, just wanting to do things I normally didn’t. I met a guy online who was in a nearby hotel to my apartment. He looked pretty good, and I let on in a sort of femme manner. I’d been sucked by a boy when young and at his requested I fucked him. We both liked it so I fucked him for about 3 years whenever we could. But I’d never been the one giving a BJ or getting fucked. I wanted that to change. I put on a pair of Joys panties and stockings under my pants and put on a crop tee I had from Dee. It was very tight and I swished my way through the lobby up to his floor. He opened the door, motioned me to sit as he was on a business call. I stayed quiet. I sat on the edge of the bed crossing my legs like a woman, and semi-posing. It was apparent the call wasn’t ending soon, so I stood up, took off my shirt, shoes and pants. His eyes widened upon seeing my thigh high stockings and see through panties. I tucked my cock and balls so it looked like I had a hairy pussy. I sashayed over to his desk and motioned to his pack of cigarettes. He gave me one and lit it for me. His eyes on me totally now, still on the phone, I was smoking and walking as much like a woman as I could, a sexy woman. I turned toward him and pulled down the front of the panties a little to show him my tucked, hairy “pussy”. I pulled them back up, sat on the edge of the bed and crossed my legs like a woman again and as sensuously as possible smoked and posed.
He got off the phone, “holy shit you;re sexy” he said. I thanked him and told him I’d like to see him too. He stripped immediately and laid on the bed. “suck me baby, suck my big cock” he told me. It wasn’t that big probably 5 inches maybe 5 and 1/2 long and about an inch thick. I thought that might be a good size though to pop my virgin backhole. I’d never sucked to completion, I felt his cum building, he had a lot of precum and I didn’t take off my mouth, I let him blow in my mouth and swallowed it all while looking in his eyes. “MMM, that was good honey, you got more for me a little later, leave another deposit deep inside my tight, tight pussy” I asked. “I don’t do that anal shit” was his reply. He wanted to suck my cock and I let him. Then disappointed, I went to my apartment, called Joy and buttfucked her three times that night. The next night with Dee she didn’t like the way I “fucked” her as opposed to “making love”. So I knew for a while I needed Joy as a fucktoy. Then when I was ready I made love to Dee.
I still haven’t gotten fucked and I want to try it.
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