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When she had said "bikini," she wasn't joking. This sucker was tiny. Maybe I was expecting something along the lines of those swimsuits you see the swimmers wear in the Olympics, but this was a lot smaller. As I put it on, I realized there was enough room in the front for my junk and the sides were super skimpy with the width of a little more than half an inch. But the most interesting thing about this suit was the back. It wasn't a thong, but it was still very narrow, exposing about half of my butt, and kind of low cut.

I looked in the mirror and had to admit I looked super gay. But also super hot. I don't know what prompted me to do this, but I turned to Jessica and asked, "So do I look gay enough for you?" "Oh, yes," was her response, "now let me make you look even more gay," as she handed me a pair of aviator sunglasses and a bracelet for my risk. Just then she did something super sexy. She got behind me and with the index fingers of each hand kind of tugged or adjusted at the seat of my bikini. And she said, "You will be rewarded later. I've got a fun surprise planned" I just then got this amazing feeling in my stomach.

I have to admit, I did feel a little odd and insecure in those first couple hours on the beach in a black string bikini. But soon it was time to go up to the room for my surprise. And what a surprise it was.

When we got inside the room, I quickly took off my sandals and shirt and Jessica then helped me take off my shorts. I was about to take off the bikini when Jessica intervened and said, "Not so fast. Leave it on and get on the bed." I laid down on the bed, clad only in the bikini, then heard her say, "Get doggy style." Right after I did this, she got behind me and put her figure on where she thought my asshole would be. She was right on target. With the tip of her index finger she massaged my asshole despite the bikini still being on. I was starting to moan.

After about five minutes, she took off my bikini and let it rest at my ankles. She then said, "Stick your ass out," and gave my right cheek a quick, easy slap as she did this. I complied, but obviously not enough, because she said, "I said stick it out." I stuck it out even more, like the bitch I was in the process of becoming, and before I knew it I felt her moist tongue probing my asshole. I loved every second of it. I moaned and must have said "Oh, God!" about fifty times.

After about ten minutes of sheer joy, she pushed me onto the bed so that I was laying flat on my stomach. She disappeared for approximately ten seconds, then when she reappeared she suddenly pinned and criss-crossed my wrists behind my back and proceeded to tie them together with a scarf. I was like "What the fu..." and turned my neck around to see what she was doing. It was then that I saw the small bottle of KY Jelly and small purple butt plug lying next to me on the bed. I tried to untie myself, but it was too late. My wrists were tightly secured behind my back. I then started frantically to say something, but just as I did a knotted scarf was shoved into my mouth.

"MMmmmph!!" was basically all that came out.
Jessica chuckled a little then said, "We are definitely going to push the envelope on this vacation, Bikini Boy!." At that very moment, she separated my butt cheeks with her hands, and I suddenly felt the cold sensation of KY on my asshole.

"MMmmmph!" I screamed as she inserted one then two fingers into my ass to loosen me up in preparation for the plug. "Oh, come on. You know you want it," was how she responded to my complaint. When she felt I was ready to receive the butt plug in it went.

The sensation was unbelievable. Jessica had used sufficient lubrication so it easily slid all the way in. And within seconds it was touching my prostate. I had never felt something so amazing before. I began to feel saliva building on the edge of my mouth, then all of a sudden I came like crazy. It must have been something like six or seven loads, but I didn't know for sure since I was laying facedown on the bed and couldn't see my cock.

Jessica, visibly turned on, grabbed a vibrator out of her suitcase the proceeded into the bathroom, where it took her just a couple of minutes to get off. I heard her screams of passion as I still laid on the bed, bound and gagged with the butt plug still in my ass.

When Jessica was finished, she called me into the bathroom, where she had me bend down then gently removed my new friend from my ass, rinsed it in the sink, and wiped my ass. It was emasculating and yet so erotic . She then untied my wrists, took the gag out of my mouth and simply said, "So sexy."

The rest of the night was a little weird. Though I had never felt so good physically, I had just been ass-raped by my girlfriend and didn't know how to respond. We ate dinner in silence and went to bed kind of early.

We woke up the next morning in silence as well. Things were still a little off, I felt. Coming out of the bathroom after showering and brushing my teeth, I saw the black bikini from a day earlier on the dresser and heard Jessica say, "Why don't you wear the same suit from yesterday, Honey. I'm also wearing a black one so we can match." This girl just wouldn't quit.

After breakfast and manicures/pedicures (her idea, to make me seem even more gay), we made our way to the beach, where I again felt a little ridiculous in a bathing suit most women wouldn't wear because of its skimpiness. After all those years of playing high caliber amateur soccer, embarking on a successful investment banking career with a number of other "alpha males," and hooking up with hot girls all over Manhattan, here
I was on my way to becoming a sissy. Or maybe even worse.

Then something clicked. I was laying on a lounge chair, then looked down at myself in this ultra-feminine bathing suit with bling around my right wrist and my manicured fingers and toes and suddenly felt extremely sexy. And I suddenly wanted it really badly in my ass. Just then I leaned towards Jessica, who was laying down on the lounge chair next to me reading, and gave her the most passionate kiss. I was ready for more, and she knew it.

When we went up to the room things got explosive in a hurry. Before we knew it we were naked and in the "69" position, but with a twist. I was the one on top, eating her pussy, and she was on the bottom, eating "mine." After she came, I went doggy again, and happily took the lubricated butt plug. But instead of inserting it as deep into my ass as she could, Jessica this time "fucked" me with it. This time I lasted about 40 seconds.

The next day, Jessica had me wearing the same style bikini but this one was blue (to match my eyes, or so she said). What was a little odd was that she was wearing a cut-out one piece. It was definitely sexy, but it was still a one piece. I asked her whether she thought it was odd that I as the guy was in the skimpier suit and she said not at all -- she thought it was actually sophisticated.

That afternoon we went back to the room for some "fun," and fun it certainly was. I went into the bathroom to take a leak and when I came out Jessica had on a strap-on and harness. I was speechless. But Jessica wasn't. "Tell me how bad you want this." "Really bad," was my reply. "I don't believe you, countered Jessica. Show me. Get on your knees." I wasn't ready for this and was like, "C'mon Jessica." But she wasn't having any of it. "If you want this to go anywhere near your asshole you know what to do." I got on my knees and started.

At first it felt weird and I had no idea what I was doing. But then Jessica said, "C'mon suck it like you mean it. You know you want to, don't pretend you don't." Just then that light bulb flashed and I realized how much I was into this. I began to suck with more vigor. "You like this, don't you?" she asked. While I sucked, I responded with an "Mmm-hmmm."

After about another minute we both got on the bed. Jessica had me get on my back and she swung my legs up and my cock was pointed up as well, towards my face. She then lubricated my ass and proceeded to take my virginity. I was pleasantly surprised at how easily the dildo fit. As she fucked me she kept saying, "You are such a sexy boy! So sexy!" It took maybe another 30 seconds before I came. I came so hard that my love juice went all over my face. Classic.

As if things couldn't get any more interesting, they did on the next day. It started right after we woke up when Jessica presented the pink string bikini she wanted me to wear that day. It wasn't like a tacky hot pink bikini, but pink is still pink. Still, the idea of being so effeminate, so vulnerable in front of this kinky, hot chick was too much to resist, so I complied. And was happy that I did....

Stay tuned for more