Holiday in Cabo


I was a 20 year old virgin in the 3rd year at St. Mary’s living in an apartment with two other girls that were anything but. While my sexual experience was zero I’d read all the books and seen videos, even some porn which I thought were pretty gross. A few weeks ago I went to a gynecologist to get a prescription for birth control not wanting to get pregnant when I finally did it with someone. She examined me and asked if I was sexually active and I mumbled, “No but someday soon I expect to.”

I thought not, your hymen is stretched but mostly intact, you’ll have it easier the first time you do it. Everything is completely normal, let’s discuss your options.

We talked about the various methods and I choose the pill. After buying the first month’s supply I started taking it on my next cycle. It made me feel excited and all grown up. I’d masturbated a little and used the smallest dildos I could find on line which I guess accounted for my hymen being stretched. All of it felt good but rarely did I have an orgasm which was frustrating.

My housemates Becky and Susan had guys in their rooms most Saturday nights and occasionally they came out of one or the other bedrooms together in the morning together so I assumed they were bisexual but they never put it on me. So I simply ignored it. Becky’s uncle Mike was spending the fall in Mexico on his sailboat and invited the three of us to come down for Thanksgiving.

We arrived at the harbor but Mike’s boat was nowhere in sight. We approached another boater and asked if he knew where Mike was at. He told us that he was anchored outside the harbor and offered us a ride in his inflatable dingy to find him. We left our bags on Larry’s boat and the four of us took off for the anchorage. I turned out the Mike and Larry were friends and we spent awhile on the sailboat which already had a few people on board when we got there. As it got late Larry offered to put us up on his boat which was larger and he didn’t have anyone else on board. Mike OK’d the idea and we motored back to the harbor. Larry’s boat was impressive to say the least with two large staterooms. Larry showed us to the very spacious front V-birth, laid out sheets, pillows and blankets. He demonstrated how to use the marine head and bid us goodnight disappearing into his room in the back leaving us to making ourselves comfortable and muss about why a such a good looking single guy hadn’t even given us a hug let alone make a move on at least one of us.

The next morning Larry made coffee and we all went to a little open air restaurant for breakfast. He asked us what we’d like to do today. “Shopping and lay on the beach.” Well why don’t you shop and meet back at the boat after lunch, we can go to lovers beach. It’s near the harbor, popular and can only be reached by boat. This sounded good so he gave us all a quick hug and we took off.

We bought some jewelry, clothes and found a spa. We got our nails done and Becky wanted to get her pubes and pits waxed. I’d always shaved my pits but at Eskort Bayan Susan suggested that I get waxed down there. We had seen each other naked getting out of the shower and getting dressed. The idea was intriguing and felt a bit naughty so on the impulse I decided to go for it, a full bald look just in case that this trip turned out to be an adventure that was long overdue. It hurt like hell when the girl yanked the wax and hair out but it was brief and for the first time since puberty I saw myself fully. I wanted someone else to see me and the sooner the better.

We headed back to the boat to change into swimwear and Larry took us to the beach. The four of us played in the warm surf and Larry looked really good in his loose fitting shorts. The bulge at his crotch was good sized and hinted that he was well endowed. As the afternoon wore on we went back to his boat to shower and change for dinner. It was a surprise that the hot water was limited on board. Only two of us could shower before the hot water ran out and we had to wait for a while it to warm up again for the rest of us to clean up.

Larry bought us dinner and we paid for the drinks. Larry left us at the bar and went back to the boat alone. DAM, I thought was he gay? Three pretty young girls vying for attention and he left us to do whatever. Much later we staggered back to the boat, drunk and sleepy.

The next morning he explained that last night he’d been on the radio with another boater that needed some help with his engine and they’d gotten the problem fixed. We all went to breakfast and parted like the previous day. Cabo San Lucas is beautiful with beaches and shops in abundance. I bought a new bikini that barely covered the essentials. Becky and Susan wanted to move from the boat to a hotel with unlimited hot water for showering. We booked a room with two queen size beds and went to the boat to collect our bags. Larry was nowhere in sight so we left him a note explaining everything. I couldn’t help thinking that I’d missed a chance to get with him in some fashion. Oh well, that’s life but at least I hoped we get to say goodbye properly.

Around 6:00 we went up to the room to get dressed for dinner. Becky and Sue showered and got dressed then headed out the door and said that they meet me at the hotel bar leaving me alone in the room. I stripped and looked at myself in the big floor length mirror. The sight of my freshly shaved pussy was very erotic. In the shower the feel of the water on my bare puss felt very different then when it was hairy. The feel of it with a soapy washcloth was likewise new and wonderful. Tempting me to masturbate but with the other girls waiting I just massaged my labia and clit a little enjoying the new sensation before getting dressed in shorts and loose blouse without a bra. The soft top tickled my nipples and looked very sexy as my boobs giggled and bounced as I walked down the stairs which felt really nice and naughty. We had some drinks and eat a great meal.

We wound up back at the hotel sitting on the patio bar and Larry walked by. Mary shouted out to him and he joined us. He ordered a pitcher of sangria and we talked and laughed at dumb jokes for an hour or so. He stood up and suggested we go out to lovers beach and build a fire. The drinks had gotten me feeling adventurous and we took off in the dingy with blankets and towels. Once there he built a fife with the coconut husks laying near the beach and said that he’d like to take a swim. That sounded good but we didn’t bring suits. “No problem” he said no body is less than a mile from here and skinny dipping is common out here at night. Becky and Susan quickly stripped to join Larry in the flesh. I wasn’t shocked or anything but not quite ready to let Larry see me in the buff just yet anyway. The three of them jumped in the surf and were laughing and playing. I thought ‘what the hell’ and took off my top.

They trotted out of the water and the sight of his shaved cock and balls bouncing made me wet between my legs. The girls climbed into each others arms, fondling and kissing. Larry laid down beside me with his head on his folded towel. I kept glancing at his stuff laying limber which was not at all what I’d expected. It was the first time I’d seen a guy naked that didn’t have a hard on. I put my head and arms on his chest and felt a burst of daring to reach down to touch his penis. He turned his head and kissed me lightly. I fondled him some more and felt him getting an erection. It was very exciting and he slid his tongue between my lips to play with mine. That part I’d done before but this time I had a dick in my hand. We kept going like that for awhile and he played with my breasts and tweaked my nipples. Now my shorts were soaked with my juice. Susan and Becky interrupted this and said they wanted to go back to the hotel. DAM, I thought my big moment was about to happen and they were killing it.

We all got dressed and headed back to the harbor. The girls dashed off toward hotel and Larry asked me to come inside the boat with him. Thinking and hoping that this might work out after all. He took my hand and led me to his stateroom. All pretense and inhibitions were gone, I was going to get fucked.

He kissed me and we twirled out tongues together and he pulled my ass into his crotch. I could feel is hard on through his shorts which was exciting then he pulled my top over my head. He took one my nipples into his mouth and teased it, then the other one. I could feel my juice running down my leg. He unbuttoned my shorts which feel easily and he knelt down to kiss my thighs and labia through my panties. He pulled them down and I stepped out to them giving him a full view of my bald pussy. He took my outer labia between his lips and cupped his hands on my ass. Ever so gently he ran his tongue up my slit and around my clit toying with it. I was getting more turned on then I’d ever been in my life. He stood up and stripped off his shirt and I figured it was my turn to do him. I unbuttoned and unzipped his shorts pulling them down. He wasn’t wearing underwear and his cock was sticking straight out.

It wasn’t huge like the one in the porn pictures but a completely respectable size. I took him into my mouth and tried to remember how to do it from the videos and books I’d read. He held the sides of my head and didn’t try to jam it down my throat. He pulled me up to hold me with his dong pressed against me as we kissed some more. He gently turned me around and pushed me face down on his bed spreading my legs apart and he pressed himself against my butt. With his hand he guided his penis to rub the crack of my ass several times then between my legs to rug it against my labia and clit. Oh god I thought, I’m going to get my cherry pooped doggy style. How wonderfully wrong I was, he knelt down and started licking me from behind and reached around to put his finger in my vagina. The tingling was getting more intense and he backed off to lift me onto his bed.

We kissed and fondled each other with growing intensity he turned to put his head toward my feet and put his thumb in my pussy while his finger explored my perineum and a little on the outside of my butt hole while he used his tongue to excite my clit. I licked the underside of his shaft and took one of his testicles in my mouth to suck on it then the other one. Out of the blue I had an orgasm. Not exactly mind blowing but quite a strong one. We kept doing this and I had another one even stronger. I thought ‘this is what’s supposed to happen.’ He drew back his crotch and continued to work on me with his fingers and mouth. A third orgasm was building but he stopped and flipped back up to face me. He got between my legs and pulled my knees up to put his cock against my clit and stoked it. I was so very ready to have him inside me and reached down to guide him to my opening. He pushed it in just a little and backed out before thrusting again, deeper with each stroke until he was all the way in. It didn’t hurt at all but I was so tight that I felt the entire length of him stretching me. He stopped for a moment and I hoped he wasn’t done. We continued thrusting and resting until I was so wet that it was getting very conformable and felt fantastic. We moved together in sync and he shuddered with an orgasm. I felt his cum fill me and when it hit my cervix I had a huge orgasm like never before in my life. He stayed hard inside me and after a short rest we thrust against each other again. I had another fabulous orgasm then he came again.

We did it in various positions and had uncountable orgasms long into the night. The next morning I was a bit sore down there but the memory of how I got that way felt wonderful. We showered and the hot soapy water made fondling very exciting as he took me from behind while we were standing up. My pussy was so full of his semen that his thrusting numbed the soreness and we went back to bed for some more rounds including some anal which felt better then I’d expected it to.

That afternoon the other girls and I had to leave for the airport. I hadn’t said more than a dozen words to them but the smile on my face spoke volumes.

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