DEBBY
Events of the last two months have changed my life completely. I met my lover, Debby over a year ago, and we started our relationship after I changed jobs. Our physical relationship has been fireworks ever since our first night in bed over six months ago. It was as if we had just discovered sex. We wasted no time getting acquainted. This lady's performance in bed, or the floor, or wherever we get the urge, can be described as outstanding. One of the things that we explored early in our relationship was anal sex, and it became a regular part of our sexual repertoire. We usually indulge in an ass fucking at least once a day. Her response to having my cock up her rear passage causes me to get even harder. She said that she had tried anal sex before, but with me it was great. When I fuck her ass, she enjoys it so much. She can fuck me for hours that way and stay continually turned on. Her favorite position is when I lay on my back and she eases my dick up her ass.
After seeing how turned on she gets when I fuck her ass, I began to wonder what it was like. After all, I have an ass too! One of the great things about our relationship is the honesty and openness. After another one of our great sex bouts, I asked her if it really felt that good. She said that it was her greatest turn on. Well, if she can cum that way, I reasoned that I should be able to also. She just smiled and said that we should investigate that. One of the other nice aspects of our relationship is that we move between roles, sometimes she is the aggressor and sometimes I am. She said that has created problems in her previous relationships, but I really enjoy it. We discussed the fact that there is a bit of the other sex in all of us, some masculine and some feminine. After all, we have both hormones in our systems, don't we? It was then that I confessed that several years ago I had gone in drag to a Halloween party and I had enjoyed it a lot. We decided to explore that aspect of my sexuality a little further.
That next Friday, she came home from work with a new outfit for me and makeup. She had bought a leather skirt, a red silk blouse, a garter belt and black hose, and a wicked pair of black five-inch heels. First I was sent to the bath- room and told to shave, everything. Off went the moustache, and hair on my legs; and for good measure I shaved my crotch. After my shower, she went to work on my face. After my face was done, I donned a curly dark wig that she had. When I looked in the mirror, I was shocked. I looked good, I would have asked myself out. I put on a bra with some water balloons, and the garters and hose. I then slipped into the skirt and blouse. For the first time in my life I felt really dressed up. I felt sexier than I ever had in men's clothes.
After she had gotten dressed, she decided to go out so she could show off her new "girl" friend. When she pulled into a topless bar, I got worried. She explained that this was the perfect place to go, I liked to go to them as a man, they were dark and the men in there would think we were hookers, so I should get lots of attention. After a few drinks I got more comfortable in my role as a lady. I decided to go play a little pinball. While I was on the machine, a tall, good looking guy came up and began fondling my ass. On one hand, I was really enjoying the attention, but I was a little scared that he might discover my secret. He started nibbling my ear, and invited me to leave. I responded in my best imitation female voice that my girl friend and I had other plans for the evening. I left him and headed for the ladies room to cool off. When I returned to the table, he was gone and Debby said that we should go home before I got into trouble.
On the drive home, she said, "Now you know what we have to put with all of the time!" I had very mixed feelings at that point, although I had enjoyed the attention, the feminine side of me was coming out; I had this fear of being dis- covered. When we got back home, Debby told me to sit down and let her fix me a drink. I was calming down a bit with my Scotch and water when the doorbell rang. She told me to stay seated while she answered the door. It was our friend from the bar. I was panicked. How did this happen? Debby invited him in and offered him a drink. I did my best to remain calm, and excused myself to the bedroom. Debby came in and told me that this was her way of fulfilling my fantasy. She said, "You always wanted to know how good it felt to be ass fucked, well, you are about to find out." It was too late to back out now. She was right, I did want to find out, but I had kind of expected a strap-on dildo or something, not a real live cock.
She said, "Let's go get him ready." I followed her out of the bedroom and headed for the couch. After we sat down, Debby asked him if he had ever made it with two girls at once. He was delighted with the idea. She grabbed my hand and we took our places on either side of him on the couch. As she went to work on one ear, I did the other. Debby began to unzip his fly as I unbuttoned his shirt. Debby had his hard eight inch dick in her hand and was slowly mastur- bating him as I slipped his jeans off. Debby help his hard dick up and motioned for me to go down on it. I began to suck his dick in the same way I like to have mine sucked. While I was doing this, Debby was getting undressed. She moved around and took off my skirt. We then laid him out on the couch.
Debby grabbed me and kissed me deeply. It was then that I realized that this guy still thought that we were both women. While Debby explored my mouth with her tongue, he started feeling my ass. Debby broke off our kiss and asked him if he wanted to eat her pussy. As she settled on his face she pulled me over his crotch. His hard dick was slick with cum. Debby smiled as I eased his cock up my ass. I could hear him groaning as I felt his cock move into my ass. After I became accustomed to the feel, I began to slowly move up and down on his cock. I was so turned on by then, that I was ready to cum any moment. Debby grabbed my dick and began to stroke it. I was now feeling the tremendous turn on that she knew all so well, and she could tell that I understood. As I relaxed, I knew the pleasure of feeling a good hard dick inside me. I began to cum, not just an ordinary cum, but the kind of orgasm that women feel. It washed over me, and lasted for a long time. When I looked in Debby's eyes as she rode his face, I could tell that she was cumming too.
When he came, I came again, I could feel him shooting into my ass. He kept driving deeper into me and I was loving it. I could feel his cum splashing into my bowels, and I came again. When his dick shrank, I uncoupled myself and put on my panties. He lay there, totally fucked out. He sat up and said that he really couldn't take any more. He got dressed and we both kissed him at the door. After he left, Debby and I had a good laugh, he never even caught on. I had explored another side of my sexuality that not too many men ever get a chance to do. I had thoroughly enjoyed the experience and I now knew what it was like to be fucked in the ass.
Since then I have been able to truly enjoy both sides of my sexuality. Few people realize that everyone has a little bit of both sexes in them, and even fewer have the opportunity to enjoy both sides of their being. I have fallen even more in love with Debby since that night, and we have explored even more exciting experiences since then. One evening we included one of her girlfriends in our special relationship. We have opened up sides of each other that few people get the chance to explore; and it's only going to get better.