Where it happened: On a cruise ship.
Langauge: English
Sex: Male
Rating: 9
Category: Straight
You’re probably looking at the intro to this page and thinking, “Twenty-eight!? What kind of loser is this guy?” I used to wonder that a lot myself. I was not the biggest dork in my high school: There was another guy who was as geeky as me, only he didn’t take baths. I was a close second, though, standing well over six feet tall and weighing around one-twenty five or so. Guys liked to prove their masculinity by pounding the crap out of me, and girls just ignored me. As a result, while most of you were learning to get along with other people, I was learning to avoid everyone. The first time I had sex was in Reno. I had gone there when I was 22, won two hundred dollars in a slot machine, and my best (and only) friend drove me out to the Old Bridge Ranch, where a very nice lady whose name I don’t remember deprived me of my accursed virginity. Naturally, I was drunk, and it was over too quickly for me to have enjoyed it, and it’s not really worth mentioning. Therefore, this is not the story of the first time I got fucked. It’s the story of the first time I made love.
When you’re a complete and total nerd like I was, life really sucks. There are a few options you have: Kill yourself, continue to live in shit, take lots of drugs, or try and change. For a long time, I did the drug thing, smoking pot 24/7 and doing what else I could, when I could. It wasn’t until I was about 26 that I began to realize exactly how fucked up my life was, and I began to try to change. Sick of my pathetic, weak, pencil-necked body, I began to work out. After about eighteen months, I had gone from 140 to 180, and just as surely as I had looked terrible before, I was looking pretty good after. The problem was my social skills totally sucked. I remember the first time a girl gave me “the look” I was so freaked out I could only stare at the tops of my shoes. Realizing that drugs were keeping me from growing up, I quit using them. Easier said than done: It took a couple of years to quit entirely.
I must digress for a moment (don’t worry, the good stuff is on the way!) to say that I’ve worked at a small bookstore from the time I started college. The owner was a nice old guy who left the store to me when he died. I was 25 at the time. For the next three years, I ran the store entiely by myself, working ten hour days, sic days a week. I was either working or working out, and on my day off, Sunday, I’d sit at home watching sports on TV. I should also mention that the bookstore had quite a collection of porno magazines, which kept me entertained during many a lonely night, much like the way this web site is keeping you entertained, ya perv! 🙂 Finally, I was ready to explode. I had to get away. I put an ad in the paper and hired some help. When I was sure that I could leave my store in capable hands, I went out and booked a vacation. Having grown up watching “The Love Boat” as a kid, I decided on a fourteen-day Caribbean cruise.
The first night on board, I thought I had made a huge mistake. I went to a get-acquainted party the first night, and there was hardly anyone my age on board, and those who were were couples. The people at my table at dinner were all in their forties, and while I got along with them OK, it was looking like my ideas about romance were sadly mistaken.
The following day I went to try out the health club on board. The ship was one of the new superliners, and had a great place to work out. I was halfway through my routine when SHE walked in. The first thing I noticed was her body, clad in Lycra shorts and a sports bra. Statu-fucking-esque! She looked like she could have been in the Ms. Fitness pageant, her body was so hard! Firm thighs, tight ass, elegantly rounded shoulders, and the most beautiful back I’ve ever seen. I was in total lust. When she looked at me, I naturally looked away (geek habits die hard). She stretched out for a while, exhibiting fantastic flexibility, then went to the stairmaster. Momentarily distracted, I returned to my workout, figuring that a woman that hot had to have a husband. In between sets, I looked over and saw she wasn’t wearing a ring, but what did that mean? She could have just taken it off to work out in. I continued my sets, occasionally glancing in her direction. I was surprised to see her looking back my way, but the look on her face was….well, just wrong. She was looking, all right, but not close to smiling. In the meantime, she had worked up a pretty good sweat, adding a glistening sheen to her athletic build that made it impossible not to look at her. I finished my workout and proceeded to the deck, where I soaked up the sun and read. After a while, she came out on the deck wearing a bikini. She took position on a chaise lounge about twenty feet away and proceeded to oil herself up. She had sunglasses on, so I really couldn’t tell if she was looking my way or not. I tried to concentrate on my book, but I was too distracted, and quite frankly, turned on. Even if she did belong to someone else, I could still look, right? I kept glancing in her direction, but she just lay there with the same expressionless look on her face.
Later, after dinner and the evening show, there was a huge party on the deck. I stopped by it for a while, and saw Ms. Fitness (as I was beginning to think of her) dancing with some guy. My dreams crushed, I proceeded to one of the lounges, where I got drunk with two of the guys from my dinner table. Later that night, after the buzz had died down a bit, I realized I had missed the midnight buffet and was extremely hungry. Fortunately, there was a 24 hour pizzaria on board, so I went up for a few slices. Afterwards, I started heading across the deck, with the intention of taking my tired ass back to my room. The party had died down, but there was still a small group of people dancing. AS I approached, I noticed that there were six women dancing in a circle, and wouldn’t you know it, one of them was Ms. Fitness. Summoning what courage I had (the alcohol certainly helped!), I just walked up and started dancing with them. It was formal night, and everyone was dressed to the nines. She was wearing a beautiful black dress that was slit way up the side, occasionally flashing a glimpse of toned, tanned thigh. I wasn’t really looking at that too much, because I was too busy looking at her face, which now had an inviting smile on it. I moved closer, smiling back, hardly believing what was going on. I was instantly erect, saved from embarassment only by the dim lighting and the looseness of the rented tuxedo pants I was wearing. I suppose there are those of you who take dancing and flirting for granted now, but when it’s your first time, it’s really something! For the next half-hour, I danced with her and her friends (who all looked a little older than her). The last song was a slow one, and we automatically moved towards each other, dancing close together (but not too close; I still had a raging hard-on!) and looking deep into each other’s eyes. When the song was over, we went over to the table where her friends were. introductions were made, and I found that her name was Heather, and she was travelling alone. It was very late by then, so everyone said good night and made for their rooms. As we parted, she gave me a wink.
It’s funny. An hour before, I had been ready to crash, but after that, I went back to my room and couldn’t sleep. All I could do was think about Heather, how beautiful she was, and how close we had been. I finally dozed off. the next day we were in port, and I did not see her until after dinner, when I ran into her in one of the lounges. She was with one of the ladies from the night before. We sat down and we started talking. We were there for hours, discussing everything from the cruise to sports (which, for a woman, she knew a lot about) to books. I noticed, though, that she never really said much about her life. Now that I was closer and in better light, I could see that she had worry lines, as if she had been through a great deal of stress recently (when you major in Psychology, you tend to notice these things). Eventually, her friend left us alone, and the conversation continued long into the night. Eventually, we decided to go for a stroll on the deck.
We were walking down the promenade when I decided to hold her hand. Pretty tame, I know, but I had to start somewhere! We walked to the front of the boat, and for a while we didn’t say anything. It was a very comfortable silence, two people holding hands underneath the Caribbean moon. WHenI broke the silence, I told her about my life, how I had been a total no-life pothead and was really getting out for the first time. She said she was very suprised to hear that, because I such a handsome young man. I just about freaked when she said this, because no one had called me that before except for my Mom! ANyway, it was her turn to drop a bomb: She told me she had married the man of her dreams right after college, and they had an absolutely perfect relationship for fifteen years. Then one day, three years earlier, he came home from work with a headache, went into the bedroom to lie down and never got up again. Dead at 38 from an aneurysm. This was her first vacation since his passing away. I felt so bad for her! I put my arm around her and held her tight. Sex was the farthest thing from my mind at that point. She went on to say that she knew that he would have wanted her to to get on with her life, so that’s what she was doing. SHe then revealed that she and her husband had both been overweight, and that she had started working out shortly after he died. “I’m really glad I met you,” she said, “because you’re proof that I can still attract a hot young guy, even if I am 40.”
As much as I was amazed at her age, I was even more amazed at my reaction. I turned towards her, placing my hands on her hips and said, “You know, no one has ever said things like that to me before. Do you know what it makes me want to do?” I pulled her close and tight and kissed her hard. She responded instantly, sipping her tongue into my mouth. I have no idea how long we stood there, kissing in the moonlight. My world had been reduced to her sweet lips and dancing tongue. We varied the intensity, going slow and soft for a while, then fast, deep, and hard. Our hands roamed across each other’s backs. Finally, we stopped for air, and I asked her if she’d like to come to my room.
“I’d like that very much,” she said, “but right now it’s 4 a.m.and I need to sleep. That way I’ll be good and rested when I fuck your brains out tomorrow night.”
“I’m all for that,” I said, and we kissed again, longer and hungrier than we did the first time. By the time we said good-night and I got back to my room, it was past 5 a.m.
I was so excited I barely slept. We met for lunch at around noon, and spent the afternoon touring in the port we were at. I barely noticed anything, though. All I could think about was what was going to happen that night. I was hard almost the entire day. We would steal kisses whisper dirty thoughts into each other’s ears, teasing each other, allowing the sexual tension to build as the day went by. We ate dinner together (“Eat well. You’ll need the energy,” she said with a sexy smile), and afterwards, finally went to my room.
Once there, things happened with an exquisite slowness. We started kissing as soon as the door was closed, slowly moving towards the bed. We sat on it and held each otehr for a while, our previous sexual bravado replaced by an intense, quiet respect for what we were about to do. We were two people whom fate had tossed together, comforting each other against a world that had dealt us a whole lot of hurt. We lay down on the bed and kissed, our tongues exploring, dancing. I ran my fingertips oh so lightly down her face, making her shudder and moan. Our kiss stopped long enough for her to say, “Let’s get naked now.”
I bounded up from the bed and had stripped to my shorts in seconds. Then we swapped places and she did a little striptease, showing off her muscularity while she did so. Down to a bra and panties, she threw her self on top of me, and we were kissing again. This time, I could feel her hot flesh pressing against my own. My hands roamed down her back and landed on her firm, tight buttocks, gently kneading and squeezing them. We continued for a while. Frankly, I was unsure of what to do next, and I didn;t really care: I was content to kiss her forever! She made the next move by breaking off the kiss and saying “Would you like a massage?”
After the answer (which was not “Hell no, that would be wrong.), she got a bottle of suntan oil out of her purse and told me to roll over. I eagerly complied, and soon had two oily hands gently caressing my back. While she worked, she told me how sexy my muscles were, and how beautiful I was, and how she had wanted me ever since she first saw me in the workout room. I nearly came against the bed, I was so turned on. She did my back and legs, then commanded me to turn over. SHe did the front of my legs, then my chest, pausing long enough for a five-minute kissing session. When she got to my nipples, she teased them lightly, sliding her fingernails around and around the tips. I never had any idea that they were so sensitive, and I moaned with delight. Stoppping for a moment, she said “Hmmm, I think that about does it. Oops, wait a minute. I think there’s one more muscle that I missed. I think it’s probably really stiff, too!” She slid her hand down my stomach and underneath the waistband of my shorts, pulling them down and at last freeing my cock. “Oh, it’s hard all right. This requires some serious work.”
She began with one finger, starting at the base near my balls and working her way up. The finger slowly circled the head several times before sliding back down the shaft. Then she started in with all her fingers, gently kneading and stroking with only the tips. I was in absolute heaven! Every muscle in my body was tensed as she continued her relentless stroking. I was on edge, ready to come, but her fingers were applying the perfect amount of pleasure, just enough to keep me on edge without coming. This went on for perhaps five minutes, until I begged her to stop. i just couldn’t take it anymore. She moved up my body and kissed me again, and once more I was lost in the sweetness of her mouth. Then I felt her oily hand grab my cock and begin gently pumping it up and down, up and down. She used less than half the pressure I did when I was jacking off, and it was beyond fantastic. “Oh, God, harder!” I pleaded, and she complied, her grip tightening, moving faster and faster. The most intense physical feeling I had ever felt coursed through my cock, spreading throughout my entire body. I grabbed the sides of the bed and practically screamed as wave upon wave of sheer pleasure wracked my body. Come flew out of my cock, some of it hitting the wall behind me, but most of it streaming across my chest. Heather slowed her strokes, gently squeezing the last few drops out.
“I take it you liked that”,she said, a smile on her face. “Just a bit,” a said, and we both laughed before kissing lightly, gently. She went to the bathroom and returned with a towel, proceeding to wipe the oil and come off my body. We kissed again when she was done, trading places on the bed as we did so. Our kiss went on for a while. My hand slowly worked its way up her body, settling on her breast, gently massaging her nipple through her bra. i began to kiss my way down her body, nibbling at her neck and shoulders before plunging down between her tits. SHe sat up and removed her bra. I immediately attacked her breasts, gently rolling her nipples between my thumbs and forefingers. I watched her face, which was twisted into a mask of lust. her eyes had rolled back into her head, and her breath was coming in tiny gasps. Then I lowered my head and took her right nipple in my mouth, suckling it tenderly for a moment. Then I kissed my way across her chest to the left nipple, doing the same. She was moaning, and moaned louder when I place my top row of teeth on her nippple and used my tongue to roll it against them. My left hand was manipulating her right nipple at the same time, and apparently I was doing it right. Her back arched, and she said my name over and over. her hips started bucking, and she cried out in pleasure, gasping for breath. I continued for a moment, finally ceasing as her breathing returned to normal. “Did you just come?” I asked.
The flush on her face was answer enough, but she nodded anyway. “That’s the first time I’ve ever made a woman come,” I said, and she looked kind of shocked. “Really?” she asked. “Are you a virgin?” I laid down beside her and very briefly explained to her my sorry sexual history. Instead of saying anything, she kissed me again and again, first on the lips, the slowly moving downward. I leaned back on the bed, realizing what was coming next. My cock, amazingly enough, had never gone soft after that first orgasm, and ever so slowly she kissed her way towards it. SHe stopped at my nipples for a while, and it felt great, but unlike her, it wasn’t enough to make me come (girls are so lucky in that way!), just enough to make me squirm and squeal with delight. Down my stomach she went, making a neat circle around my erection and winding up on my inner thigh, kissing and nibbling on it. Then she licked her way up to my balls. I had never had anyone lick my balls before, and when she started to, I nearly came right then and there. I had no idea they could be so sensitive! After a minute or so of that, she grabbed my cock at the base and pointed it towards her mouth. Her eyes locked onto mine, she encircled my cockhead with her lips and slowly, gently began to suck my cock.
After my previous orgasm, I had thought that nothing could feel that good. She happily proved me wrong. Her hot, wet tongue and lips worked magic on my seven inches. I was pretty relaxed when I started out, and every time I would start to tense up she would stop and kiss me. This went on for a long, sweet time. She would tease me to the brink, then stop. She repeated this five or six times. Then, after we had kissed, she whispered, “I’m not stopping this time. Feed me.” SHe went down on me once again, but this time there was nothing gently about it. SHe attacked my swollen cock, sucking it hard and fast, her tongue racing around the head and up and down the shaft. The sound of licking, smacking, and sucking, along with her breathing heavily through her nose filled the room, along with my ever-louder moans. I came again, equalling the intensity of my first orgasm. Heather continued to suck until I had to beg her to stop; my cock was so sensitive it was actually starting to hurt! She quickly started kissing me again, and I could taste my salty semen on her lips. I didn’t care at all. In fact, it turned me on even more. i flipped her over onto the bed and began kissing my doen her body once again. I fiercely sucked on her nipples. “Yesss!” she hissed through clenched teeth. Going down further, I sank my teeth into her panties and pulled them down and off her. Since I was at her feet, I paused for a moment, then started sucking on her toes. I licked the soles of her feet, then began working my way upwards, gently nibbling on her calves and thighs. Lightly, I brushed my tongue across her neatly-trimmed bush. She gasped in pleasure, then moaned loudly as gently kissed her pussy. I began licking it with long strokes, and she started to writhe about on the bed. My tongue brushed against her clit again and again, until finally I stopped with my mouth right on it. I paused for a moment until her eyes met mine, then I started sucking on it. Gently at first, the a little harder. I could tell by the expression on her face that she was loving it. SHe grabbed the sides of the bed, her athletic sinew standing out with the strain of her efforts. She threw her head back, screaming “Aaah, aaah, aaah!” I sucked harder and her body went completely stiff, her hips quivering uncontrollably. As her orgasm subsided and she relaxed, I eased up pressure. I gave her pussy a final kiss before once again moving up beside her.
We talked for a while, praising each other for our oral efforts, then just lay there in each other’s arms for a long time. At that point, i didn’t even care if I fucked her or not, although my cock was soon ready for more. SHe felt it moving against her and started kissing me again. Without a word, she rolled on top of me, straddling my hips as she did so. SHe lowered herself onto my cock, then leaned forward against my body. We didn’t even move for a while, utterly content with mere penetration. The sensation of her hot, clinging pussy on my cock felt magnificent. Maybe a little too much so. When she started to move up and down, I was so excited I came almost instantly. I didn;t really enjoy coming, either, as I did it before I wanted to. I apoligized to her, and she just laughed. “You’ll make it up to me next time, I’m sure.” She was so understanding!
After that, we took a shower and went to bed. She was right: i did make it up to her the very next night, fucking her so hard that the people in the next room called a steward to come out and tell us not to make so much noise! We averaged three times a day for the rest of the cruise. There were some days where we could barely even walk! When the cruise was over, she sold her house in the Midwest and moved out to California to be with me. We don’t fuck every night; probably only twice a week or so. But every six months we take another cruise, and boff each other silly. Must be the salt air.
Heather is visiting her folks back east right now, while I mind the bookstore. We recently met an interesting young woman at the gym we both go to, and I hope to soon be writing about my first three-way. TTFN.
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