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Finally, I Pleased A Man

"After several years transitioning, I experienced intimacy with a man"

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I had been living full-time as a woman for over three years. My wife, Helen, and I had settled into our life of living together as women. Of course, we still enjoyed intimacy with each other, and we were still exclusive. However, sex together had changed. My “boy things” no longer worked and were becoming very small. Helen had my boobies done as a gift for completing beauty school. My breasts were very sensitive from hormones. As women, Helen and I had discovered breast play. I was very much a woman and I loved it.

We had a circle of friends – mostly "hair girl" I met working at the salon. There were eight of us who ran together - one other couple like us and four single girls. Someone suggested that we take a vacation to the beach in the spring. It sounded like a great idea. Someone had a connection, so we rented a four-bedroom condo on the beach on the Alabama/Florida border.

There was so much preparation. Both my wife and I needed beach wardrobes. I had nothing and it was so much fun planning and shopping for beachwear. The big question was one-piece or two-piece. Actually, I was scared to death to appear in public in either. Helen decided - it was two-piece. Since bikinis only come in one size, we got one of those big plastic tubs and stocked it with a dozen bikini parts of varying neon colors. In the mornings when we headed to the beach, all we had to do was pull a top, a bottom, and grab a cover-up.

When we got to the condo, everyone was excited about getting out onto the beach. I was so worried about the experience – mostly issues of whether or not I passed as a woman. My wife insisted I wear a two-piece to start things off. I was so glad I had a cover-up as we walked to where we placed blankets.

After dropping the cover-up, my wife dragged me immediately to walk the shoreline. Her instructions were to throw my shoulders back and be proud of myself as a woman - saying, "We had paid a lot of money for those boobies so flaunt them."

I felt good, I was getting looks, I loved it!

By the end of the week, we were all sorry the trip had to end. Our "goodbye" celebration was a seedy beach bar. We all wore our bikini tops with fancy, skirt-like cover-ups. Helen and I often "dare" each other so tonight we both wore string tops that showed most of our boobs - Helen is 34DD and I am 36D. Of course, it was a night for our strapless four-inch straw wedgies. I had been practicing walking in them for weeks. Helen insisted I was a natural with the way I had learned to sway and wiggle as I walked.

As the evening got late, one of the other girls asked me a very personal question – she wanted to know if I had experienced sex with a guy or at least sucked a cock. I was horrified and didn’t answer. Everyone was paying attention to my answer, and I was completely tongue-tied.

Helen answered for me and said, "The answer is NO on both counts." That was all they needed and all seven of them (my wife included) took it as the challenge for the evening.

The bar was a real dump, and the restrooms were outside at the end of a long and hidden path. The eight of us went to the path and separated into two groups. One group stayed at the beginning of the path. The other group took me to the point where it separated to go to the men’s room or the girl’s room. When a guy came onto the path, the first group asked if he wanted a BJ saying they were initiating a girlfriend into their sorority. Of course, no guy in that dump ever said no. Then they brought him to me and circled us. I had been told that I should immediately go to my knees in front of him, bring his cock out, and suck it capturing his cum in my mouth. I was not to gag, and I was not to spill a drop.

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They brought the first guy. He was wearing loose basketball shorts without a belt. I kneeled in front of him, easily got his cock out. I was so afraid! I just quickly took him into my mouth and started working his shaft with my hand while working his pecker head with my tongue. Thankfully, he was excited and shot right away. Since I didn’t have him very deep, I was able to keep the cream in my mouth. It was so warm. The taste was spicy and to my surprise I liked it. Not knowing what else to do, I swallowed his whole load. Then I cleaned him with my tongue and put his cock back into his pants. I was so embarrassed but looked up at him and smiled.

The other girls, especially my wife, were so surprised that I was able to get him to cum so quickly. They all insisted that I must have done it before, but I continually denied it. I did tell them, "Remember, I have a home-court advantage."

To this day, years later, they often call me "Home Court".

Quickly they brought me a second guy. This guy was wearing jeans, and it was more difficult to get him out. However, he was also excited and filled my mouth with so much very warm cream. I was surprised that any guy would pump out so much cum, but I was ready and swallowed every drop again. After I had sucked the eighth guy, they released me. My wife said she was so proud of me. Now I was a real woman in their eyes.

All week long the group had played "Mix 'n Match" in the bedrooms at night, except us. That last night, however, two of the girls wanted Helen. Surprisingly, she acted horrified. All week long all of eight of us had pranced around the condo in various states of dress or undress. Of course, we knew they were intimate with each other. However, it was something she just had not considered.

Helen, at first, declined, but they were not deterred. Then a third girl joined in the pursuit. Helen looked to me for support, but I told them to all, "Go for it."

I yelled to Helen, "Just remember pushing me to my knees an hour ago?"

They pushed her down on the sofa. Two of them held her arms while the third moved between her legs to start eating her pussy. The girl between her legs was so good that Helen's protest quickly became sounds of passion as she had her first orgasm. She no longer resisted. The girls stopped holding her and they changed positions. Two sucked her tits and the third was on her pussy. She climaxed again. At this point, Helen begged to taste pussy herself. I left the three of them to their passion.

At some point, Helen returned to our bed. We all slept late that morning. It was leaving day. We all packed and headed to a late breakfast before returning home. On the drive home, Helen and I talked about so many things. It had been a week where we had both crossed a line. For my part, I had been living as a woman for three years, but we had remained exclusive. Now I had sucked a guy's cock. For Helen's part, not only had other women tasted her sex honey but she had tasted theirs.

Finally as we reached our driveway, she said to me, "Every woman needs a little meat with her salad every now and then." We admitted that we were both bi and that's how we moved forward with our lives.

Published 
Written by Mitzie
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