One fun vacation (Part 1)

[funtimes444]

I've read a bunch of posts on the board and they've been amazing and fun to read. So much so, that I'm now ready to come out of my shell to tell my story, which happened about six years ago. It's kind of long, so I'll ask you to bear with me -- it'll be worth it as in the end you'll see how mind blowing it is.

Before I begin, I guess I'll give you all some background. I'm currently a white make in my 30's. I was born and raised in an affluent suburb or Philadelphia. I had a fairly "normal" childhood in that both my parents were professionals who had a pretty mundane marriage but stayed together. My younger sister and I were "normal," suburban kids who had nice friends, received good grades, participated and excelled in sports (field hockey for her and soccer and tennis for me) and ultimately went off to prestigious colleges and embarked on successful careers.

But that's where the normalcy ended for me. Though post-puberty I was a good looking kid who was always in shape (a hair over 5-10 and about 170 pounds) and never had trouble getting girls, I was mostly bored out of my mind with most of the chicks I met. This didn't change when I moved to Manhattan out of undergrad to take an investment banking job. These were the "loosey-goosey" days on Wall Street when the money was flowing and guys like me ran around The City like they owned it.

For more than the first half decade I was in Manhattan nothing really changed. During the week, I worked hard at the bank, and during the weekend, I worked hard at the bars picking up girls who bored me to death.
Then I met Jessica and everything changed.

I first saw her at my neighborhood supermarket then at the gym, where the place was chock full of young, pretty girls -- all in amazing shape -- who were living off their parents as they tried to complete their Mrs degree by landing a wealthy banker, lawyer, or ad exec. Despite the dozens of hot chicks on the treadmills, stair masters, and ellipticals, there was something about her that really caught my eye.

Maybe it was the tight shiny spandex that accentuated her amazingly taut 5-04, 115ish pound body, or maybe it was her dark curly hair (at a time when every chick in Manhattan was trying to straighten her locks) and piercing brown eyes, or perhaps it was her sensual walk, the way she shook her ass just a little as she moved around the cardio room. At any rate, just looking at her made my blood boil like no girl before her.

We finally met one day as we exited the gym at the same time. She actually spoke to me first my saying, "You don't miss a day, do you?" That was my in. Within two minutes I had her laughing and within five I had her phone number.

The first several dates were a lot of fun. Each time we went for dinner and each time the conversation was free-flowing. Surprisingly, unlike a lot of hot girls in Manhattan with wealthy parents, she was down-to-earth and easy to talk to. We also shared a lot in common like favorite food, movies, etc. But there was something else, this sexual tension that we had, even though in the beginning we didn't do more than kiss good night.

I should have known something was up when at the start of the second date, she looked at my pink Hugo Boss dress shirt, ran her hand gently down my chest and said sweetly, yet seductively, "Love the shirt." She then delivered a five minute monologue on how too many guys in New York were "boarish," had no sense of style, and had to get in touch with their feminine side. Again, I felt the blood boiling.

I guess I'll stop here for a second. I think a big reason why I had been so bored with women up until that point was that I was never attracted to girls who liked boarish men. I mean, I played sports my entire life, but they were soccer and tennis, not football. And speaking of football, I wasn't the type of guy who would spend his Sundays wearing the jersey of his favorite team while stuffing his face with wings, chips, and Michelob. Oh, and while we're at it I liked to read (things other than the sports pages), didn't mind shopping and "metrosexual" wasn't a four-letter word.

Getting back to the story (and don't worry, it will get REALLY hot REALLY soon), as Jessica and I continued to spend more time together we realized we shared even more in common. And when we finally slept together -- around our tenth date -- it was great. While we didn't do anything remotely kinky, it was by far the best sexual experience I'd ever had. Her body was as good as advertised, she was well groomed, and she had this unbelievable intensity about her, especially when going down on me. And, I'll say she felt the same about me.

Things progressed nicely and within a few months it was winter, and we planned a great get-away vacation to a five-star resort in St. Martin. And about two weeks before we left, things started to get exciting.

We were out for dinner one night and were taking about some of Jessica's gay friends (and she had many of them) when she confided that she had "a thing" for gay guys and found "hot" ones "sexy." She also mentioned that she enjoyed watching gay porn. None of this really scared me and before I knew it the main course came and we devoured our meals.

Later that night, however, as we were hooking up and she was massaging my balls, she suddenly went "south" to a region she had never been to before (at that point in my life only one girl had ever gone there before, and like most guys, I quickly moved her hand away). But this was a different time and a different kind of girl, and before I knew it, I was experiencing pure, unadulterated ecstasy as Jessica's finger, aided by the Vaseline she kept on her night table, probed my butthole. She didn't say anything -- she obviously enjoyed hearing me get completely turned on and, to be honest, she was quite turned on by this herself. I came without even having sex, and, once I ejaculated, there was no mention of what had just happened.

The next two nights were carbon copies of the night described above. We'd hook up, I'd eat her out till she came than she would finger fuck me. I LOVED it. In fact, I would fantasize at work, on the subway, and at the gym about it. But it went unmentioned between us.

On the fourth night a strange thing happened. Instead of putting her finger in my ass, Jessica teased me by massing my balls then gently caressing the area underneath them, but when it came time to insert her finger between my cheeks, she never did. She could so tell how badly I wanted it and actually gave this sinister, shit-eating grin when she saw how much she was tormenting me, but that was it. I had to "settle" for plain, vanilla sex.

The same thing happened the next several nights, and Jessica obviously loved tormenting me. She'd blow me for a little while, lick my balls, and even lick right underneath my balls, but when it came time for either her finger or tongue to touch my asshole she'd fold up shop and start kissing me. Man, I wanted her to play with my ass so bad, but was just too afraid to say anything.

Several night before we were due to leave, we had a little fashion show in her apartment. Jessica, who worked as a PR Agent in the fashion industry, decided she was going to go shopping for me and "dress me" on this trip. I've told you already that I'm fashion forward, and since I liked the way Jessica dressed herself (super sexy, yet classy), I didn't have a problem with this. The result was plenty of linen pants and shirts, designer sandals and loafers, and even a man purse. None of this really phased me.

Later, we had just gotten into bed and were lightly kissing and caressing each other when she asked, "So did you like what I bought you?" to which I responded that I did. Then suddenly she added, "Listen, there's something else I bought you and I don't know how you'll feel about it, but I'd really like if you wore it." I was totally confused by this point and responded with a "Try me." She took the slightest of deep breaths and said, "I bought you some bikinis that I'd like you to wear."

At first I thought she meant women's swimwear, which, despite my open-mindedness would have been odd. Then I realized she meant what was known to most of us as "Speedos."

"Oh, so you bought me some Speedos?" I asked. To which she responded, "Speedos are what 16-year-olds wear for swim team. Bikinis are what hot guys wear on foreign beaches."

I guess I seemed hesitant because just at that moment her finger magically appeared super close to my butthole and she whispered sensually in my ear, "Baby, if you wear a bikini for me I will give you an amazing rim job." I was sold.

Before we knew it, we were taking off from LaGuardia Airport in 34 degree blustery weather only to land mere hours later in an 87 degree tropical paradise. Within minutes, we picked up our luggage, cleared customs, and caught a cab to the beachfront luxury hotel.

It was around 3PM and we were both in a rush to go outside and grab a couple hours of Caribbean sunshine before it got dark. I stripped out of my winter clothing and was about to put on my board shorts when Jessica said, "No fucking way...you promised" as she handed me what almost looked like a girl's panties.....

Stay tuned for more

[funtimes444]

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

[funtimes444]

From some reason, we were out on the beach really early that morning before almost everyone else. However, there was this gay couple there. Both guys were in great shape and very attractive. As Jessica and I stripped to our swimsuits, I could tell they were eyeing us. Or, more precisely, they were eyeing me. Like dessert. Jessica noticed this. And when one of them threw an obvious smile my way, she threw one back in his direction.

Jessica said, "You know, he thinks you're hot." I then asked, "What do you think of that?" "I love it," was her reply. "Seriously?" I shot back. "Definitely," she said. "Let me ask you something," she continued. "Assume no one would ever find out, would you ever have sex with another man?" At that point, I remembered the conversation we had had much earlier when she told me how much she was into gay guys and loved gay porn, and I thought how sexy it would probably be for me to be that vulnerable in front of her. So, while I didn't think of myself as gay, I responded, "I'm not sure I'd be into it, but I wouldn't rule anything out." I guess she was kind of pleasantly surprised by my response and answered, "Really?"

"But let me ask you something," I continued, "How would you feel about me sleeping with another guy?" Her response was, "I don't know if I could share you with anyone, but I love the idea of it." Finally, I asked, "Top or bottom?" "Oh, bottom," was her reply, "Totally bottom. So sexy." I then looked over at her and it looked as if she was in another place.

I soon made my way to the ocean, which means I had to pass our two new friends. I could feel their eyes boring into me, or, more precisely, into my pink bikini-clad ass, but kept walking. Only once I made it into the water did I turn around and noticed that Jessica was walking towards them, smiling and talking to them as she approached their chairs.

It was extremely warm that day so I was in the water for a while. When I came out, I couldn't find Jessica (or the gay couple) but thought nothing of it. When she did reappear I was like "Made some new friends?" and she said, "Yeah, they're super cool and they invited us for drinks at their place later. Their condo is just down the beach a little bit." Little did I know the trap I was about to walk into.

Mid-afternoon, Jessica was ready to go for drinks. I picked up my shorts and was about to put them on, when Jessica stopped me and asked, "What are you doing?" "Putting on my shorts," was my reply. "Come, on you don't need them. It's just a short walk, "she countered. "Plus," she added, "I'm not wearing my cover up," which kind of was a big deal considering on this day she had decided to wear a thong bikini.

So, here I was, walking to these gay guys' condo wearing nothing but a pick string bikini and flip flops with my girlfriend whose fantasy it was to see her man with either one of these guys.

It started off innocently enough. They greeted us at their screen door with mimosas. I looked at the guys. They were about our age and both good looking. Both were well built and wearing tight boy shorts. Skimpy, but nothing like what I had on. A little flamboyant, but not completely over the top. This would be just fine, I convinced myself.

We got inside and were just standing around, making small talk. Finally, of them looked at me and said, "Jessica, I love his bikini. How in the world did you ever get him to wear one?" Jessica, who was standing right behind me, took her index finger and traced a line up where my ass crack was and replied, "Oh, I can be VERY persuasive."

The one guy then touched my bikini in the front, dangerously close to my package, and said, "You know, you look gayer than us in this." Before I could even venture a reply, Jessica chimed in with a laugh, "Why do you think I'm making him wear it?" "So, a fag hag," the other one answered. "Totally," was Jessica's response.

Just then the one guy grabbed my drink out of my hands and pinned my arms behind my back. We were about the same size, but for some reason I couldn't set myself free. And to be honest, I wasn't sure I wanted to. The other guy then reached around a sofa and pulled out a scarf -- Jessica's scarf. Just then I realized what she had been up to when she had temporarily disappeared. They bent me over the couch and tied my arms behind my back. I started to say something but as soon as I did, Jessica said, "Let's gag him." Next thing I knew, the one guy pulled out a red ball gag, and as he inserted it into my mouth said, "Open wide, Sweetheart."

So, here I was, bound and gagged and clad in a pink bikini -- just the way Jessica liked. They one guy took me by the arm and led me up the stairs. He then had me get on the floor on my back. He took off my bikini, and when he did, it was obvious that I was aroused. "Well," he started, "I wasn't expecting to find this!" Just then, Jessica grabbed the guy next to her and they started on what became a very passionate kiss. "Mmmmphh!" I started to protest, but to no avail as the kiss continued. The kiss eventually ended, at which time Jessica said, "Now, Honey, you know how much I like gay boys." At that point the guy who had taken off my bikini bent down and took out my ball gag. He then leaned down to my face but didn't have to go very far as I met him halfway and we can a hot little kiss of our own.

"Very sexy," Jessica said, as she gave me a wonderful kiss.

At that point, a steel cock ring was attached around my throbbing cock, and I was turned over onto my stomach. My ankles were then bound. The guy that had kissed me produced some KY and filled my ass with it. Then he began to probe with his finger. I was moaning big time, but that came to end end when the other guy stuck a big dildo in my mouth and was like, "You better not let this come out." I nodded meekly. Then I felt a big vibrating dildo inserted into my ass. I turned around and noticed that it had wires attached to it, and these wires were attached to some sort of control box, which had dials on it. I guess the one guy saw what I was looking at and explained, "These dials control the intensity of the vibration. Watch. You are in for the ride of your life." Just then he turned the deal and the vibrating got faster.

I was literally convulsing on the floor, experiencing pure, unadulterated ecstasy and moaning through my dildo gag. If this was what it was like to be gay then I was in.

Just when I thought I would cum, the intensity was turned down. And three minutes later it was turned back up again. This literally happened for twenty minutes. While I was in my own personal paradise, both of my new friends had taken off their boy shorts and were jerking each other off. And Jessica was "cheering" me on. "You like this, Honey, don't you? Yeah, I bet you do. Nod if you like boys?" I nodded. "Do you think we should come back to play tomorrow?" And I nodded again with more conviction. "

Next thing I knew it rained cum -- lots of it -- into my face. Both guys had shot their load simultaneously, and my face was the recipient of all that hot goodness. They soon left the room and headed back downstairs, so it was Jessica and me at the seen of the crime. She took one look at me -- cum al over my face bound with serious bikini lines and big dildo stuck up my ass and another one in my mouth and simply said, "So sexy."

I couldn't disagree.

[shaulis]

Funtimes444, I like your story. It was a fun read. Thanks for adding your story

[sebbie]

A lot of erotic movies primarily intended for straight males contain episodes where two womemn are masturbating each other, often employing a vibrator or strap-on dildo. The camera normally pans between the women doing each other and the guy, who is invariably shown playing with his own genitals as he watches the goings on.

This story is a variation on that, going the additional step of saying that at least some sexual and at least mostly straight females would get great enjoyment out of watching two (or maybe three!) guys do each other. As I think about this, I don't find anything weird or odd about that at all.

To me, the other part that makes the story interesting is the role that tiny, snug-fitting male garments play in the overall male (and perhaps female) arousal. I fully realized that gay guys often enjoying seeing each other in such garments and use them routinely as part of sexusl play.

But so many women have publically claimed that they are deeply offended and definitely not aroused by seeing guys in tiny briefs that I assumed that this could not be a sought-after turn-on for women, if at all. This story suggests that I am dead wrong on all of this. The only part I'm not sure about is whether this is a story that really happened, or just an erotic male fantasy by a guy author who would have LIKED these events to have occured. Same for the butt plugs and related anal stimulation. I think a lot of males regardless of sexual orientation are often reluctant to admit to their partners that they are turned on by such activity. At some level, the fear is that the partner might not regard this as "normal" sexual activity. Gay guys as a group tend to be more open-minded on what sexual activity is considered normal versus not normal, but this could still be an issue with them.

As some of you know, around the house I am usually found wearing some sort of pretty snug athletic wear in large measure because I need to be wearing something that works well when I am rowing and weightlifting off and on throughout the day. But I also sometimes end up out in my front yard wearing the same garb, going after my mail etc. Neighbors of all ages see me and wave. While I'm usually not standing there in just a 1" Solar brief, some of the stuff I am routinely wearing fits pretty snug. Not a single neighbor has ever complained to me that I shouldn't be outdoors wearing such clothing. In fact, a few of the women maybe are a bit fascinated, and perhaps even secretly wishing that their husband would follow my lead, but I am still studying their reactions in further detail.

Sebbie

[funtimes444]

I've been travelling and apologize for taking so long to respond.

In response to Sebbie's post, yes, this story was very real.

I totally agree with a lot that you said, though there is a caveat. As women get older, they tend to become more open minded. In my case, Jessica was already well into her 30's -- 33 or 34, I can't remember -- and had pretty liberal, open-minded parents.

Also, my bikinis definitely set the stage for our "unconventional" sexual behavior. I remember at times during that vacation being on the beach wearing those skimpy, tight suits and feeling very sensual, sexy, and even a little vulnerable and effeminate and I loved it. And, I'm not going to lie, wearing them made we want it in the ass. To this day I take on a different sexual persona when I wear them.