Susan & I often traveledto the Caribbean for our vacations. We loved the laid back atmosphere and all the sun and gorgeous beaches. Last year though we arrived to find that the airline had lost my only bag containing all my clothing including my swim suit! Imagine arriving in the Caribbean without even having a swim suit to wear!
I had just resigned myself to going down to the gift shop to purchase a pair of those crummy over priced swim trunks they sell when Sue spoke up.
“You could always just wear a pair of my panties to swim in. They don’t look much different from the Speedo’s that you like and then you don’t have to waste money on a suit that you will never wear again anyway. Here, why don’t you put on this purple pair?”
She held out a skimpy purple pair of her bikini panties to me.
I was stunned, but thrilled by the idea. The idea of walking around in public, shimmering from head to toe with suntan lotion wearing nothing but a pair of my girlfriend’s panties was totally hot! I gulped and took the filmy nylon panties with on trembling hand. Sue noticed and looked down at the growing bulge in my pants
“I see you like my idea a lot.” She smirked. “Well, if you do everything I tell you to do today, perhaps you can wear a pair of my panties everyday that we are here, even if your luggage gets delivered.”
I could not get my voice to work so I merely nodded in reply.
We quickly shed our clothes and changed into our “swim wear”. Sue donned a fantastic black bikini that showed off her spectacular breasts and was high cut to show off her great ass and just barely covered the thin vee of blond hair that she left on her virtually shaved puss. She looked incredible.
I stripped and pulled the purple panties up my legs to my thighs. As I pulled the panties up the material stretched until I thought it might break, but it didn’t. I settled my balls and cock in the tiny panties and pulled the back down to cover my ass cheeks. Then I turned to look in the mirror. The panties were extremely snug and hugged my ass making it look terrific. From the front they were just high enough to cover my cock with a little tuft of pubic hair showing. The panties stretched across my cock showing off the ridge line around my cock head and the nylon material glistened in the light.
Sue grinned at me. “They look wonderful on you. But we are going to have to trim that hair, how unsightly.” With that she grabbed a pair of scissors and pulled down the front of my panties and trimmed all my pubic hair down to ½ inch in length.
“I am going to be so proud of you as you walk past all the women they are going to be gaping at the package that I am with. I predict that at least one woman will want to know where you got such a great suit!” she exclaimed.
With that she waltzed out of the room with me following in a daze. I felt like all eyes were upon us as we emerged from the lobby and walked around the pool. I felt somewhat uncomfortable with everyone watching us and wanted to take the first empty seats that we came to, but Sue would not hear of it. We actually circled the pool twice before she found some chaise lounges that she liked on the opposite side of the pool from the bar.
We sat down and Sue immediately ordered me to cover her with suntan lotion.
“With pleasure,” I replied.
She lay down on her front and undid the clasp of her bikini top. I slathered lotion across her back, neck and down her sides. I rubbed it down under the top of her bikini bottoms and all over her legs paying close attention to the tops of her thighs making sure that I brushed my hand against her pussy many times as I “worked the lotion in
”. When I was done, she held onto her top, rolled over and waited for me to do her front. I again went to work starting with her face, shoulders, neck and arms. Rubbing plenty into the exposed flesh of her breasts, abdomen and again working her thighs until I saw a wet spot on the crotch of her bikini.
Then it was her turn to slather me with lotion. She spent a lot of time on my abs and thighs too, making certain that her dripping hand brushed over my throbbing cock many times while she worked. Then she had me roll over and did my back. When she was done she decided that she wanted me to get her a rum drink from the bar. As I walked past many of the women at the pool looked at me covertly over their books. Each seemed to be admiring the way my cock jutted out of the front of my “swim suit”.
I was beginning to really enjoy this, especially as the tropical heat was really starting to make my organ heat up in its little tiny nylon prison. When I returned with the drinks, Sue decided that it was time to go for a swim. I hesitated. It suddenly occurred to me that if I dove in the water the panties would slide down my body. If I slid slowly into the water, they would stay in place, but would essentially become translucent once they got wet!
Sue saw my hesitation and reminded me that, if I wanted to wear the panties the rest of the week, I had to do everything that she told me to do. I shrugged and went to the side of the pool and dropped in. The water was fantastic and I tried to stay in as long as I could, but Sue had other ideas. She said after a few minutes that she needed one of her hair doodles and asked me to get it for her. I climbed out of the water and felt the water cascading down my body. I glanced down and sure enough my cock was very visible to anyone that wanted a look, which only caused me to get even harder than I already was. As I walked past one of the hotel windows, I glanced at my reflection in the dark pane and saw that my ass cheeks were just as visible. I got even harder at the thought of showing off like this. I got the doodle and climbed back into the cool water. Sue moved to me and ground her pussy against me.
“Ooooh, you should see the way all the women and even some of the guys are admiring your special swim suit and the way it clings to your sexy ass!” she coo’d. “I bet that there are at least 14 wet pussies and 7 raging hard ons pool side that would like to fuck my little panty clad boyfriend.”
She got out of the pool, while I decided to swim a few laps so that my hard-on would subside a little before I climbed out of the pool. When I got done, I saw that there was a stunning brunette talking to Sue. As I came over to our chairs she smiled at me, turned on her heel and strutted away.
“Who was that?” I asked as I sat down, watching the shapely girl return to a tall blond and very attractive woman wearing a two piece bathing suit that showed off her flat belly, firm breasts and tight sexy ass.
“Her? Oh, that was just Tish. She and her girlfriend Jess were just wondering where you got your swim suit.”
“You, you, didn’t tell her did you?” I stammered. I could feel my face flushing red with the heat of my embarrassment. It was one thing to be walking around wearing a pair of your girlfriend’s wet panties in public, but it was another thing for a beautiful girls like Tish & Jess to know that I was dressed like a sissy.
“Of course I did. I told her all about how your bag was missing that that we decided to have you wear my panties to the pool rather than wait for your swim trunks. Tish suspected that they were panties when she say you walk by and she was thrilled to hear me confirm it,” Sue replied.
I groaned inwardly.
I spent the rest of the afternoon was spent in a delicious haze of arousal as Sue kept me excited by dipping me into the pool to keep my panties transparent and then parading me around so that all the other pool patrons could keep an eye on my rock hard cock and panty clad ass.
“I’ve had enough sun for one day,” Sue said around 3 o’clock. “I’m going back to the room to get showered and changed for dinner. You can stay here for as long as you like.”
She bent over to kiss me and strolled back to the room. I decided to dose in the sun for a while and woke up around 4:30 and headed for the room.
Upon my return, I found Sue looking fantastic in a white blouse that was sort of sheer with a sexy black push up bra underneath and a black mini-skirt that showed off her long legs encased in sheer black hose and the pair of stiletto heeled black patent leather shoes. She had me pose for her as she snapped several photos of me in her sodden clinging nylon panties. Then before I could even open my mouth she ordered me to go into the bathroom and carefully rinse all of the chlorine out of the panties that I had been wearing all afternoon. I walked into the bathroom and as I gazed in the mirror at myself stroking my cock through the shiny nylon, I realized that I was sorry to have to remove them, they felt and looked so sexy, but I did. After thoroughly rinsing out the panties I hung them up to dry and jumped into the shower and cleaned up.
Once I was dry, I wandered out to the bedroom. Looking around I realized that my bag had still not arrived. Before I could say anything, she grinned at me.
“I see that your luggage has still not arrived,” Sue stated.
“You are right, I guess I will just have to wear the clothes that I wore on the plane down here to dinner, since my suit case is not here.”
“You certainly will not!” declared Sue. “You will march right into that bathroom and shave yourself smooth, removing all the hair on your body except your pubic hair and put on this lingerie and dress and we will go out to dinner.”
“I’m going to what?” I stammered, eying the sexy black lingerie and white dress that she had laid out on the chair by the bed.
“You heard me,” she snapped. “Since you enjoyed being a sissy so much today, we are going to complete the look and then go out. And from the angle of your cock you like the idea as much as I do.”
I could not deny that the idea appealed to me and what else could I do anyway? I loved to wear women’s things, but I had never worn them with Sue, and had certainly never gone out in public wearing them! I went into the bathroom and carefully shaved myself smooth. It took quite a while and I had to be very careful not to nick myself. Finally I was done. I went out and fastened the black garter belt around my waist and rolled up the black hose in one hand and slide it expertly up one smooth leg and fastened it to the garter. As I prepared the second one, Sue commented, “From the looks of the way you put on those stockings you have done this before haven’t you?”
“Yes, I have,” I confessed.
“Good,” she replied, “I thought you might have.”
I pulled up the second stocking and fastened it to the belt and stepped into a pair of black patent leather stiletto heels that Sue held out to me. Then I pulled the panties effortlessly up my shimmering legs and then put the bra on, stuffing it with several pairs of nylons to fill the cups.
Sue lay back on the bed and pulled her mini up to her waist exposing the tops of her stockings secured by a black garter belt and a tiny black thong. She spread her legs and told me to come and eat her. I knelt down before her and put my face to her panties. First I licked the panties until they were damp with my saliva and her juices. Then I pulled the skimpy thong to one side and proceeded to give her a tongue lashing to remember. I was down there for at least forty minutes and Sue came no less than six times. Before I was done, I was able to slide three fingers up her pussy and two fingers up her puckering ass. She ground her pussy against me each time she came. When she was satiated, she reached down to stroke my rod inside the tight little satin panties. After bringing me to the point where I was ready to come, she jerked her hand away and gave me a deep soulful wet kiss on mouth.
Licking her lips with a smile as she said, ”I just love the taste of pussy juice.” She then handed me the white dress she had laid out for me to wear. The dress looked like that one that Marilyn Monroe wore with an adjustable halter strap and a deep v neckline to draw attention to my cleavage. It had an empire waist that made it very feminine and the dress flared out at the hips with a swishy pleated skirt that begged to be twirled on a dance floor.
I slid it on and adjusted the material. As the dress draped itself over my hips, I heard Sue whistle. I took a glance in the mirror and was stunned by my appearance. The dress fit perfectly, just dropping to about the lower part of my thigh and covering the tops of the stockings. It fit well too in the chest and hips where I was much bigger than Sue. I wondered where she had gotten a dress and black patent leather high heels that would fit me.
Sue sat me down and began applying makeup. When she was done I could hardly tell that I was a guy. The foundation covered my light beard and the eye makeup was fantastic. My lips were crimson and looked very sexy. She had put a silver Tiffany heart necklace around my neck. I was glad that I had rather longish dark hair which looked very natural brushed back and clipped with a barrette to keep it in place.
“Lets go Vicki!” she said.
“Vicki? Who are you talking to?” I asked.
”Why you dear. I can’t very well call you Ted dressed as you are can I?” Sue inquired.
“Umm, no I guess you can’t. But Vicki?” I asked.
“Sure, you will be Vicki Cox for the rest of the night,” she replied.
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with this note attached, it has been posted without my permission.
<a href="https://www.lushstories.com/stories/crossdressing/caribbean-vacation-part-1.aspx">Caribbean Vacation part 1</a>