My older woman lover 55F, gave me her virgin nephew to help transition.

I met Fran at a nudist beach. She was 55 at the time, black hair past her shoulders and a very very hairy pussy. I was only 16 at the time and a virgin. It was my first time at the nude beach and it was crowded. She offered to let me lay out next to her. She had on a one piece with the top pulled down. Her tits were hanging down, but still nice D cups with dark nipples. I had my shorts on and she told me not to worry just to take them off. If I didn't I'd stand out. I did and she complimented my cock. I asked why she wasn't exposed below and she said that she hadn't trimmed her pussy and it was in an all natural state, very very hairy and most women at the beach were totally bare, or at least closely trimmed. As we were talking I mentioned that it was hot seeing a woman with black hair down there. Against her white skin her hair was really a contrast. She pulled them down and revealed her pussy to me. She had put sun screen on me, and I mean all over, including getting me hard. I was embarrassed and she said not to be, she was complimented that an "old gal" like her could get a young "stud" hard. I offered to rub lotion on her, She rolled over and I did her back, her butt, between her thighs, down her legs. Then she rolled over. I was feeling all over and under her hanging tits, down her belly, her side then up her legs. "Don't forget the rest" she said. "I definitely don't want a burn down there". I was rubbing her lower stomach and she spread her legs. Soon I was going between her thighs and her pussy lips and she was moaning. She brought a towel up over my hand on her pussy and reached under and had me rub her pussy especially on her clit. She came, then put more lotion on my cock till I shot off on my belly. She wiped it up and invited me to lunch. In her place naked she gave me my first BJ, then we ate, I licked my first pussy, then she let me fuck her.

That went that way for almost a year. On summer break I was spending most of my time there. She said her nephew was coming to stay the summer with "us". I thought maybe the sex and the normal being naked in the apartment having pussy, mouth and ass on demand was over. She said it was not. Her nephew was coming there because he was 15 and feeling more like a girl than a boy and she'd let him dress and act like the girl he felt he was. She was right, he was very attractive as a girlyboi, his hair was down to his shoulders, and he had a soft, thin, feminine body and face. Within an hour she was in the bedroom giving him his makeup and styling his hair. SHE emerged looking positively beautiful. Fran was starting to use this French cream she had, I guess a hormonal thing, that actually made his chest little puffy tits. Small to say the least, training bra size and that's what the "niece" started wearing. Her "clit" was pretty small too, about an inch thick and only 4 inches long when hard. 3 Days into her stay Fran was sucking my cock, me on the couch and Fran on the floor. Teri, the now "niece" was watching. I was moaning at one of Frans better BJs, and she brought Teri down to the floor with her. She was showing her how to do it and before long Teri was finishing the BJ. Fran told me to warn him when I was going to cum. I warned and shot off into her mouth. It was her first BJ.

Fran had a small party, everyone dressed, me in a suit for some reason. Teri was in her bedroom, and then Fran told me what the plan was. We were to have a mock wedding ceremony, me and Teri, my bride. I asked if it meant that Fran and I wouldn't have sex anymore and she said NO, it was going to continue, I'd just have someone else to have it with also. So in a mock ceremony, Teri came out in a short, white minidress her incredibly hot legs and ass framed perfectly. We did some vows, had a party. Then it was out turn. Everyone gone, Fran took Teri into the bedroom, and when I went in, Teri was dressed in a beautiful white set of lingerie. See through nightgown, her tiny tits with rosebud nipples showing through. White garter and tan stockings, with white lace panties. It was that night that I was to fuck Teri for her first full on sex. Lying in her garter/stockings and panties. I was on top of her kissing her, kissing down her neck to her soft breathing and moans. Then sucking on her tiny little titties, softly pinching the nipples, I went down. I pulled her panties down exposing her hard little clit. It was my first time sucking a cock. She exploded in my mouth. I moved back up kissing her again. "I didn't know you'd do that" she said. "I wouldn't, it was my first time, but if even for the summer, you're my wife and I'm your husband, we should make each other feel good not just me. She added "Fran took out the plug I've been wearing and put a lot of vaseline inside me and on the outside. She said if you would to put some on you too". I gave her the tube and moved my hard 7inches up to her and she rubbed it all over me. "Do you want me to roll over?" Teri asked me. "No, just like this, I want to see you, I want to kiss you, I want to suck on your titties while we make love" I answered. It was tender and good, I took my time and when into her slowly. Fran told me to do it slow, and to have her push out her first few times, like she was going to the toilet. It would make it easier. With Fran I just had to put it in her like it was her pussy, she was used to getting buttfucked.

I made slow love to Teri, and I came up her tight boipussy. It was that way for the summer. I would take her out on dates, we fucked, sucked, I even sucked her in front of Fran to Frans surprise. The last few days I even sucked Teri hard, lubed myself up and sat on her clit. I let Teri fuck me.

That was the only time I did anything with another guy or transfem. I loved it, it was great, but she looked like, sounded like, and fucked like a teen girl. I fucked Fran for another 6 months, then had to go to England for grad school. I never saw Fran or Teri again. Now I'm married have 3 kids, and have a three hole, kinky wife. I'm content but have very fond memories.