Starting Out Right
Hey it is Georgia! A few years ago I met a wonderful man and helped him get to where he wanted to be. Like I said I am Georgia and live on the east coast. I am 5 feet 7 inches tall, 115 pounds, auburn hair half-way down my back, perky breasts that fit comfortably into my 34 B size bras, and now 32 years old. I have always been a girlie girl and liked my boyfriends with a certain appearance.
Let's back up a bit to four years ago to when I started dating David. David was not my typical type. I have long preferred men that are somewhat fit, muscular, caring, and trustworthy. Don't we all want that? David was different. He was slender, not overly muscular, very caring and trustworthy. At first I dated him because I was between boyfriends and he seemed like a good companion, but as I got to know him better and better I liked him more and more. He was good in bed and knew how to please me right from the get go. His mouth felt like a small helicopter twirling on my clitoris, his hands pinched my nipples just right, and knew when the time was right to insert his penis into me to give me explosive orgasms. But David had a secret.
It took about two months after we started getting intimate for me to understand this. He was always complimenting me on my lingerie, in particular my panties. To me this was a little strange for I was not wearing exceptionally cute panties. I primarily wear bikini style or high cut panties for I have found them to be the most comfortable and honestly I think my butt looks great in them.
One day we were fooling around. I had undressed David and was between his legs. All I had on was my bra and panties. I caressed his balls and licked his shaft from the bottom to the top over and over and over. His penis was leaking pre-cum like i had never seen before and once in a while I would move up and lick it clean. But lo and behold more came out. So I did it again and again. One time this was getting too much for David and I knew he wanted to cum, but instead of letting him shoot in my mouth or on my face I pulled off and started talking to him. I did this over and over to him. I now know that this is called edging. This also made me very wet and knew the gusset of my panties would be soaked.. I took my panties off and instead of throwing them to the floor I put them in my hand and ran them up his legs and rubbed his nut sack with my panties. I moved up and started jerking him with my panties. This was too much and he exploded into my panties. They were almost completely soiled from my nectar and his cum. David immediately passed out with a big smile on his face. He was out cold so I took them to my mouth and licked his cum from my panties then i sucked my nectar from them too. I had in the past sucked my juices from my panties and also from the panties of others. You see I am bi. I really like women and I really like licking a woman to multiple orgasms and after she is exhausted I like to move up and sit on her face and rub my wet and sticky vagina all over until I get the relief that I need.
I had enough time to rub myself to 2 quick orgasms before life was restored to him and he woke up.
The following weekend we were fooling around again. This time I was down to my lingerie again and David was still in his boxers with an erection being very noticeable. We kissed for a long time and moved down to lick and suck on my breasts after I took my bra off. I pushed him down because I wanted him to lick me between my legs. He went lower. David liked eating me, but i had another plan. I could hear him sniff my odor and then feel the wetness in my panties. I told him to take them off of me, which he did. Instead of throwing them on the floor I watched as he brought them to his face and smelled them and licked the soaked crotch. I pulled him down and his face went between my legs where I had two very quick orgasms. The first was more powerful than the second. After the second one I pulled him to me kissed him hard on the mouth and gripped his penis inside his bowers. I moved down and took his penis in my mouth. My panties were in his reach and he grabbed them and started sniffing and licking them once again. I watched him with my panties as I felt him get more and more excited and him came in my mouth. It was a larger and more forceful load than I was used to. Everything was set.
The next time we got together it was the middle of the week and i had to be up early the next morning. Instead of spending the night together I left after an extended session of making out and groping. I left with sticky panties and i am sure his boxers were stained with precum.
Two days later we got together. David was in a pissy mood for some reason and would not tell me why, though when we started making out his mood improved a bit and his erection could not hide what he was feeling or what i was feeling in my hand. We were still on the couch and i had David slacks and boxers off. He looked kind of goofy, still wearing a shirt and socks but I did not care. I got up and moved away from David reached up under my dress and pulled my panties down and off. Then I got down in front of David and said, "Here let me help you put these on". His face went red with embarrassment but he did not stop me. I think his erection got harder once my panties were pulled up to his waist. Then we talked. I asked him how he was feeling at that moment and he replied "different". "How do you feel different?" I asked. Then he said that the panties felt very nice and comfortable. I am not sure how they would be comfortable since he had a big erection inside of them. We still had to get some dinner so i told him to put his pants back on but keep the panties on.
We had a lovely dinner. Later that night i had my desert. I sucked his hard penis through the panties he was wearing and had him cum inside them. I would not let him take them off and made him sleep wearing them. I slept in my cami next to him and he was wearing my panties. It was a blissful night.
The following weekend we got together once again. Though this time I had a small box for him as a gift. Inside were 3 pairs of panties, one bikini style in white, one thong in black, and white high cut in pink. Before opening the package he said I shouldn't have got him a gift, but after he opened it, he was surprised, and somewhat taken aback. It was then I told him that I knew he liked wearing my panties so much that he needed to have his own. He bowed his head not in shame but knew that I was right. I told him that from this point forward I would be expecting him to wear panties whenever we got together. He did just that. Then i noticed a change. He started wearing panties that were not one of the 3 that i bought him.
One night I asked if he would like to dress completely as a woman and go to a club with me. Oh he blushed and said "Yes". Then I said we should go shopping to get you some clothes. He looked at me and said, "there is no need to do that, I have clothes to wear." Then he took me to the extra bedroom. I never did understand why a single guy had a two bedroom apartment. This bedroom was not like a guys it was more feminine. He opened the drawers to the dresser and it was full of panties, bra, stockings, camis etc. The closet had a dozen dressers, slacks, skirts and blouses hanging, there were 6 pairs of female shoes and on the dresser was makeup, a makeup mirror and jewelry. Obviously he had been dressing for a while.
Then David turned to me and said, "I have been dressing for years". This was sweet news to me. I like the idea of David being feminized. I told David that I would be back in three hours and get himself ready for a date. I returned with an overnight bag because I knew I was staying the night. David, or as I now call him Darla, was ready and looked gorgeous. He had on black skirt, white blouse that was see through and a very lacy cami underneath. I did not know at the time but underneath his bra and panties were both white lace, his legs were shaved and nails painted red. He had on a mid length blonde wig and his makeup was impeccable.
We had a great night out and returned to his place for nightcap. We made out and I liked kissing his lips coated with lipstick. I liked feeling the straps of his bra as my hands roamed over him. It was making love to a woman for he was soft, so smooth, and smelled feminine. Darla went first to the bathroom and took off her wig, makeup and removed her blouse and skirt, but left her bra, panties, and cami on. I was next and took my bag with me and removed all my clothes and put a shirt dress on. But unknown to Darla I also put on my strapon. I knew she would like it. We got in the bed in the extra bedroom and romped around from kissing feeling each other, then she felt my strapon and she squealed. Darla moved down to look at it and started kissing it. Then she took it in her mouth just like a woman gives a guy a bj. I could tell that she really liked it. After 10 minutes she pulled off and said "I want it in me". Did i hear that right? How did she know that is what I wanted to do. Darla got onto all fours, looked over her shoulder and said "Fuck me Georgia". I got behind her and slowly inserted my 7 inch strapon toy into her bottom. She moaned and told how good it felt. After 15 minutes of alternating my pace and depth, Darla started to orgasm. It was amazing to see her have an orgasm that originated from her anus. I had never had an orgasm that started in my anus before, then i had never been fucked in the ass before either.
David started dressing more and more and around me until it seemed each time we went out we went as two women. Sometimes we would find other women to be with or a guy. Six months ago we broke up. David is now living full time as Darla and has a wonderful boyfriend. I am still looking for the right person, whether it be a man, woman or another sissy.