I guess first some descriptions. I’m Tammy, 24 and bi. I and only 5ft. 3in and weigh 105lbs, have B cup boobs, pink nipples, nice shape, with nice legs leading to a nice ass. I’m told I’m pretty, not beautiful but as one guy described it “girl nextdoor pretty”. I have black hair and keep a 2 inch wide strip on my cooch. I have only made it with two guys, I don’t really go out of my way to have sex with anyone, but in college I had lesbian sex with two other girls. I found that much more satisfying than lying there and letting a guy pound his hard cock in and out of my soft pussy. I met Sarah 26, at work. She and I were in the same department and had several overtime and weekend hours together. We would work late and be the only ones in the office. Sarah is taller 5ft. 9in, weighs about 135 but she has a great body and is a natural blonde. She has a nicely hourglassed body, small boobs which I like, they are A cup with small dark nipples. She has a super great looking body, is positively beautiful with a nicely shaped ass and legs that are super sexy.
She and I got around to girl talk, and after she admitted she preferred women to men, I told her about my limited experiences. We started hanging out together a lot, after work drinks, dancing, shopping, movies, dinners etc. I was having a great time with her. It was after about 5 months as I was in the car to drive her home. She leaned over in the parking garage and kissed me. Not a peck either, a real, romantic kiss. I had to rub my thighs together it got me wet. I kissed her back and found her hand inside my blouse and I did the same to her. She rarely wore a bra so I was the first one to start sucking on one of her pretty little A cup boobs. Her perfume was intoxicating only getting me wetter, then pulling one of my boobs over the bra she was sucking on me. Then she broke off, looking away yet still holding my boob in her hand. “What’s wrong?” I asked her. “You don’t know me, you don’t know about me” she answered. I told her I knew a lot about her, and that I really felt she and I would be right together. Looking at me eye to eye she added “No, you don’t. I’m on hormones, I’m trans. I’m sorry, I shouldn’t have kissed you I know it changes things, how you feel about me, but I couldn’t help it, I’ve come to really like you so much after our time working so hard together, and hanging out the way we do. I love, I love it all”.
I was still silent, taking it in. “Did you say you were trans? You mean?” I hesitate. “I was born a boy, but never felt like one. I knew I was a girl even as a little kid. So when I got old enough I started going through therapy and making the transition”. I asked about her boobs, her face, her body they were all so feminine, no body hair. She had been on hormones for 8 years. Her boobs never really grew past the larger A cup they are now. “And what about down there?” I asked looking at her miniskirt. “I still have it, the penis, but it’s much smaller now since the hormones, I can barely get erect anymore but sometimes I have. It’s not a problem though, I don’t have to, or even really want to use it during sex.” she said. “You said you prefer women like I do” I told her. Yes, she did, as a young teen she was raped by a married man in his and his wifes bed. He made her do oral, then made her stay around and get him hard again and made her have anal sex. He fucked her, or back then him. That led her to try to be a gay guy but didn’t like being fucked in her ass or having guys cram their cocks down her throat. She even tried masturbating while a guy was having sex in her but it didn’t really help. Mostly the gay guys she was with just wanted sex, and to leave, not to date, or have any feelings in a relationship.
I told her I wasn’t sure what I would want from that point on. She pulled off my boob putting it back in my bra and fastened her blouse. Straightening her mini skirt she told me she understood, but hoped we could still be friends and it wouldn’t stop us hanging out together. I told her, “I said I wasn’t sure what I would want, not that I didn’t want to try. I feel the same way about you, we have a real connection. I don’t know how it would work out, but I want to see. If it can’t work out sexually or relationship wise, then let’s hope we can still go back to what we have now. But, I think the next step is to go to one of our places and probably get naked”. She was shocked and happy about it and we went to her place, it was closer.
On walking in and shutting the door, we couldn’t keep our hands off each other. Stripping and kissing, sucking boobs in the living room standing up she reached into my panties and was rubbing me perfectly. “We’d better get to a bed, and NOW” I said. She asked if I wanted her to keep her panties on, she would if I wanted. I didn’t want that, I wanted to see her, feel her, be with her totally. We both took off our panties and she gave me the best oral ever, and I after a 2 year abstinence went down on her 5 inch, thin “clitoris”. She only cums a very little, almost like my last boyfriends pre-cum amount.
It was great we spent the rest of the weekend having sex, and enjoying each other. After a month, she was erect from my mouth. “I want you inside me, I want to feel you in me, and I want you to know what I’m like inside” I told her. She nodded her head and I got on top of her inserting her into my pussy.
Our sex is great, and I never thought that I’d ever even know a transwoman, but now my lover is one.
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