Cross-Dressing Vacation with Wife Ch. 01

This is my first attempt at a story. Hope you all like it. Comments are very welcome.

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It all started when my wife (Staci) and I had a conversation about how comfortable women's clothes looked and we both laughed and I boldly said, "I would wear women's panties and satin pajamas because they look really comfortable." Now keep in mind that I have always had an affinity for women's clothing, so when she was ok with it, naturally, I was super excited. Anyway, we started talking and decided to order some lingerie for me online to sleep in. We ended up buying a satin and lace short and top set. I was disappointed when it came in. It was very cheaply made and quickly broke.

Staci and I went shopping the day after I ordered the PJs and went to Wal-Mart to look at panties for me to wear. We bought 9 pair for me in all sorts of colors and all with lace. From the moment I put that pair of panties on, I was hooked. We went shopping again and we bought a couple of satin nighties for each other and all I can say is "WOW!!" The feeling is indescribable, no way was I going back to my uncomfortable male underwear and pajamas.

We started talking about how cute certain outfits were or how cute certain shoes were and pretty soon most of our conversations were about feminine things. It was and still is exhilarating. At this point in the story, I started wearing panties everyday under my clothes and nighties every night.

One day we were having one of our girly conversations and I jokingly said "Wouldn't it be hot to go out of town where no one knows us and have a girly week-end with me in drag." Astonishingly, she was all for it. I was only joking and Staci was ready to go out with her husband in drag for a week so we started planning our vacation out of town.

Next thing I know, I was obsessed, buying dresses, rompers, heels, stockings, makeup, wig and all the accessories to put me fully in drag for our vacation in Key West. My wife and I started getting our nails done together, and even started doing each other's nails at night. It was so exciting and scary thinking about being in drag in public, especially with my wife.

As the weeks went by, we perfected my dressing technique and make up as well. More and more, our sex lives were becoming hotter and hotter. We were talking about the kinkier side of sex and having fantasies about dildos, butt plugs and strap-ons. I bought a chastity cage so I wouldn't get hard when I was wearing feminine things.

I already shaved my cock, balls and ass, I figured what the hell, so I shaved my legs, chest and armpits as well. Staci and I were having so much fun exploring this side of me and we even talked about other girly getaways in other cities in the future. I love my wife with all my heart anyway, but I love her so much more for allowing me to indulge in this fetish a bit.

The day came to leave for vacation and i was so nervous and excited, I felt nauseated. My wife assured me that we were going to have a blast so I calmed down and just enjoyed being in her company. We talked the whole flight down and even during our layover in Miami. The more I relaxed, the more turned on I got thinking about the upcoming week.

It was 2:00 pm by the time we arrived at the hotel, I was on nervous, scared, and excited all at once. Staci's reassurance that she loved me and supported my affinity for cross-dressing and was even excited to embark on our newest adventures really boosted my confidence. We checked in and found out where a salon nearby was that catered to cross-dressers and made an appointment for both of us.

After a short nap, Staci and I started getting ready to goto the salon for our makeovers. I was in my lilac, sheer, nylon and lace boy shorts with my cock tucked away in it's cage, long brown wig, beige wedge heels, a really cute little white romper with a floral pattern and light makeup. Staci wore a knee length sundress with a really sassy design. Everything else was similar to my outfit and I have to say we looked pretty damn good.

It was surreal walking to the salon dressed in women's clothing in public for the first time. Never had I experienced so many emotions at one time, scared, nervous, excited and even turned on, but people were very friendly and accepting of us. It was about 6 blocks to the salon and as we walked, once again I found myself becoming even more comfortable with all of this. It was an amazing feeling. We treated ourselves to full makeovers, including nails, hair, makeup and massages. It was 5 pm by the time we were done, so we had a light dinner and went back to the hotel to rest and get ready for our first night in the clubs.

Staci and I started getting ready at 9 and the first thing she did was to lock my cock in chastity and secure the key around her neck on a gold chain. Next came the vibrating butt plug with a pink jewel on the end. This guaranteed that my ass would sway when I walked. After that was done, she started getting herself ready. I wore a pair of purple ass-less panties, a purple mini-dress, black garter belt, black thigh-high stockings, and 4" black strappy stilettos. To accessorize, I had a gold chain around my waist, gold and pink dangly earrings, a wedding ring of Staci's that we had sized to fit me, it was gold with a one caret diamond, and some plain gold hoop bracelets on my wrists. My fingernails and toenails were shaped and painted a medium glitter pink. Staci had an outfit very similar to mine except she had on black lacy satin boy-shorts. Pretty soon we were looking like a couple of hot sluts on the prowl for the biggest cocks we could find. In reality, we were cross-dressing husband and beautiful wife out for some girl time together.

We got in the cab by 10:30 and headed to the clubs. I had taken a Xanax and my buzz was very nice. My confidence was boosted from walking through the hotel lobby with people turning their heads to watch us walk out. The cab driver was a large man with tattoos, piercings, and muscular build. He was pleasant and watched us alot in the rear view mirror, especially when we were making out and running our hands all over each other.

He gave us his card when we arrived at the club and told us to call him anytime while we are on vacation if we needed a ride. We thanked him and made our way into the club. I could feel the butt plug making my ass sway when I walked and it was turning me on being there in drag with my gorgeous wife and I was in heaven. I almost wanted to leave right then, go back to our room and make love to Staci all night long, but we had planned on bar hopping in Key West's gay community. We both had planned waited for this for three months. We were not going to pass up the opportunity to explore the more erotic side of our relationship.

As we walked through the club, we saw people that were scantily dressed and even some that were partially undressed, men and women. We quickly found a table and sat down to watch the crowd and get a better feel for the place. Staci and I both ordered drinks, Cabernet for me and Vodka Cranberry for her.

We were having a great conversation when two guys came up to us, they introduced themselves as Terrell and James. They asked if they could join us and we said yes. They were both black men, very tall and well dressed. I had another glass of wine and popped another Xanax as my buzz was starting to subside. We all started talking, and they asked us alot of questions about us and why I was dressed in drag. We told them that we were just getting started into this lifestyle and this was our first time out together as well as my first time at all. As it turns out, they were living in the keys about 30 minutes outside of town and were out to have some fun.

Terrell and James were best friends and they told us they liked to seduce white couples where the husband cross-dresses. We told them we weren't looking to go that far, but they were welcome to stay and chat. They graciously accepted and we all ordered another drink. They talked about the cuckold lifestyle and even introduced us to some of their cross-dresser friends.

We were all feeling good when a fast song came on and Terrell asked me to dance. I graciously accepted and he led me to the floor. Staci stayed at the table with James and continued to chat, watching us the whole time. We were bumping and grinding on each other and having a great time. Terrell got behind me and I could feel his very large cock grinding into my ass while we danced. His cock felt huge as he ground it hard between my ass cheeks... I was getting a little uncomfortable and was about to suggest we take a break and go back to the table when a slow song came on. He quickly turned me around and pulled me in close. I tried to protest and Terrell put his finger to my lips and softly whispered in my ear, " Just go with it baby-doll." I looked at Staci and she was preoccupied herself, deep in conversation with James. Terrell just pulled me in closer, grabbed my ass with both hands and kept dancing, whispering in my ear to go with it, relax and enjoy the sensations.

Next thing I know, James had pulled Staci onto the dance floor and was dancing with her as well... His hands were on her ass and she was dancing very close, so there was no way I was getting rescued anytime soon. Terrell pulled me in closer and grabbed my ass while we were dancing. Now I am not really into guys, but he was strong, smelled good and for some reason I was really getting turned on by him and his movements. His cock was really hard by this point and he made sure I felt it... I looked over at Staci and James had placed her hand on his cock right there on the dance floor. She was obviously getting turned on too as he expertly dance with her and you could tell she was getting turned on as well. The DJ played two more songs and we finally went back to the table to relax for a bit. I was very relieved because my heels were killing my feet and desperately needed to rest. We all returned to the table and ordered another round of drinks.

As we all sat there talking, I had a really good buzz going. Terrell and James were very charming, complementing us and paying for our drinks. Terrell placed my hand on his cock and I looked at Staci for some help, but she was feeling really good as well... Her date was kissing her neck and openly fondling her tits right in front of me... I suddenly realized that I was rubbing Terrell's cock through his pants without being prodded to do so and my cock was straining against it's cage I was so turned on. The guys excused themselves and went to the restroom, leaving Staci and I to talk. She looked at me and asked was I ok and I told her I was ok, but didn't know how to feel about what was happening. She slid over on my side of the table and put my hand to her pussy, It was soaking wet. She was not only turned on by James, but it also turned her on to see me getting into my role with Terrell. She said she wanted to see where the night went... It always gets me really horny when something turns her on, so I agreed to see how things went.

The guys returned and it was our turn to go freshen up. When we returned to the table, the guys took us out on the dance floor for one more slow dance and suggested we take the party back to their place. They said they had some herb and were welcome to partake. They even said they would go back to our hotel so we could get some clothes to sleep in as well as clothes to wear the next day if we liked. We had a plan, paid our tabs and left. We got to their car and were separated again. Me in the back with Terrell and Staci in the front with James. We stopped at the hotel and each grabbed a nightie, fresh panties, sundress, makeup and any accessories we would need for the next day. The guys wanted to take us to breakfast and shopping the next day, so we packed some really cute sundresses and wedge heels to wear for our day with them. We freshened up a bit and got back into the car.

It was about a thirty minute drive and Staci quickly snuggled in close to James. Terrell pulled me in close to him and we made small talk for the first few minutes of the drive. With the combination of the Xanax and wine, I had a really good buzz so I didn't realize that he had pulled his cock out until he placed my hand on it. He was huge. He had to be at least 10 inches long and so thick I could barely wrap my fingers around it. My mind was racing, I had never had my hand on another man's bare cock before and it was certainly not what I had intended to happen, yet I found myself starting to stroke his hard throbbing cock and was turned on by the feel of it in my hand. It was so soft yet hard and really warm to the touch. I came to my senses briefly and tried to protest, but he whispered in my ear to enjoy exploring my femininity. By this time I was too far gone to put up an argument.

I looked in the front seat and Staci had shifted positions. She was slowly stroking her date's cock which was a bit smaller than the one I was holding, but still quite large... Leaning against him, with her legs spread, he had gained access to my wife's pussy and was fingering her while she stroked his hard cock. I was jolted back to reality when Terrell turned my head to him and kissed me full on the mouth. I was too far gone to resist, so I just let it happen... He tweaked my nipples through the thin material of my dress and squeezed my ass firmly. I have to admit, it was really turning me on even though I was not gay. His cock was leaking precum steadily now and he was gently nudging my head toward his cock. I quickly sat up and told him I was not ready for this quite yet, so he just kept kissing me and put my hand back on his cock. This is how things went for the rest of the drive. I was really starting to get into it after Staci looked back and told me to take my time and enjoy what the night had to offer.

More to come in chapter two... Where would the rest of the vacation lead us???