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- debby1.txt
-
- 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. It was then that
- we decided to explore that aspect of 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 bathroom 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 discovered. 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 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 masturbating 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 then 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 a going to get better.
-