First Time Anal

A couple of years before we decide to get married, Beth and I took a vacation in Jamaica. It was a glorious change in weather from home. We left home on the fifteenth of February where it was minus fifteen degrees Celsius and there was already just shy of three feet of snow accumulated in the yard. The snow banks on the side of the roads was higher still. With a forecast of more snow we went to bed the night before our departure with feelings of trepidation, that the morning might bring the bad news that flights were canceled.

We awoke to clear skies and sunshine and caught a shuttle from the motel, where we could leave our car at no additional cost, to the airport, only fifteen minutes away. Things went quickly at the airport and we were soon on our way to sand and sunshine. We left early and with the time difference, arrived before two in the afternoon to sunshine and a temperature in the mid eightys.

Before we had even left the airport, a local entrepreneur was trying desperately to sell us a cone about six inches long sealed at the top by folding the thin cardboard over on itself. Inside was an unknown quantity of Marijuana or as he called it, "Ganga". We weren't interested and realizing he wasn't making a sale, he walked off to find someone else. There was a big shuttle bus with the hotel name on the side and along with twenty or more people, we loaded luggage and found seats. A half hour later, after driving through lush countryside, we hit the populated area where the hotels were located.

Having collected our luggage, we entered the two story hotel and waited our turn to check in. There were several staff members behind the front desk to look after new arrivals but only one of them held my attention. There was a tall woman, possibly in her early thirties wearing a colorful dress that was struggling to contain her large breasts. The material of the dress covered a fair amount of her breasts and tied behind her neck leaving a lot of cleavage exposed showing a deep valley between them and a little of both inside curves when she leaned down. 😍😍 Her hair was short and curly and there were several laugh lines on both sides of her eyes. Her skin was the color of milk chocolate and she had a very pleasing laugh during her conversation with the couple she was dealing with.

It was finally our turn and once checked in, we learned that the hotel didn't have a restaurant but the one on the beach did and also featured an all you can eat buffet every night. Our room was on the second floor overlooking the pool. The patio door opened onto a decent sized balcony with a couple of chairs. On the balcony, we could see that the hotel was a "U" shape with the pool in the middle and a walk way fifty yards or so from the back edge of the pool with a railing. We took care of unpacking quickly leaving us with plenty of time to check out one of the queen size beds in the room. We had to change into cooler clothing but once naked, well, you never want to waste an erection.

Beth pulled the covers down and crawled to the middle and lay on her back before spreading her legs. The view as always for me was breathtaking and one I enjoyed every time I got to see it. Beth is a natural blonde so fair skinned and even with a tan, not very dark. She has shoulder length curly blonde hair parted in the middle and it frames a pretty face with a small nose, full lips and startling blue eyes. Without shoes she is 5' 4" but depending on heel height has on rare occasions been 5'8" tall. On the rare occasions she has worn heels, the calf muscles are more pronounced and makes you want to caress them. Her waist narrows and then flairs to wider hips. The cheeks of her ass are firm and well defined. This for me is a hand magnet and I frequently caress or simply grab one cheek or the other simply because I can.

Looking at my girlfriend lying on the bed, my eyes drifted from her face to her breasts with nice erect nipples to her flat belly and the blonde hairy bush covering her offered pussy. Getting into bed with her, I dove face first between her legs. The next fifteen minutes or so was spent licking, sucking and nibbling until I heard her screaming in pleasure and my face was suddenly wet from her orgasm. With the first one out of the way, now was the time to slide up and in. My stiff cock met no resistance as I slid into Beth and she moaned with delight. A slow steady pumping and some attention to her tits and nipples did the trick and a squeal of delight signaled her next orgasm. "Ooohhh fuck that was good! You need to fuck me harder and faster Doug.

Without removing my cock from her tropical hot pussy, I learned back on my heels so I could rearrange her legs. Once I had them spread further apart and her knees up I learned forward placing my hands on the bed near her armpits. Now in the right position I started pumping my cock into a very receptive wet cunt. Apparently I wasn't pumping fast enough became Beth said "Come on Doug you can fuck me harder than this! Make me scream! Fuck me faster!"

My hips rose and fell rapidly and soon with genitals hitting genitals, a slapping sound and heavy breathing was all that could be heard in the room. The exertion caused sweat to form on my forehead as I continued to fuck her. The tightness of her hairy pussy gripping my cock was getting to me so I warned her that I was ready to erupt. "Come on honey, make your juicy cunt cum all over my cock! I know you love to be fucked so cum for me!"

This seemed to do the trick and what started as "OMG, OMG, turned into a Ooohhh fuck that's it, yes, fuck me harder I'm gonna cum!"

Beth's orgasm was loud and her ass bouncing on the bed triggered my orgasm. I emptied my balls deep inside her pussy. While lying in bed beside her, I realized that the little bit of dirty talk may have had something to do with Beth's orgasm. Definitely something to file away. A little while later and a short walk, got us to the dining room of the other hotel. All you can eat buffets provided what we needed to go with pleasant conversation. We wrapped up super with coffee and dessert before taking in a floor show and were back in our room before ten. The long day had finally caught up with us so, into bed and asleep quickly.

The next morning while walking through the lobby heading for somewhere to eat, we saw a sign announcing that there was going to be a wet T-shirt contest pool side at two this afternoon. Beth told me that we needed to be back so she could enter the contest. Just as we went out the gateway before the road, there was a small building that had been hastily erected so a mother and daughter could cook and provide food for the laborers who were currently renovating a hotel on the other side of the road. The special of the day was conch and dirty rice. We got one serving and two cold sodas to eat on the way to the beach.

Brunch finished, we walked along the beach looking for just the right spot. When Beth saw a washed out area that provided some privacy on both sides, she announced that it was the spot to spread our towels. We lay on our towels soaking up the warm sunshine but after ten minutes, Beth became restless and started rubbing between her legs. She sat up to unfasten her bikini top and dropped it beside her. Lying back, her hand went back to rubbing which worked the material of her bikini into her pussy. There wasn't much material to start with and now at least half of it was inside. The thick blonde bush was getting wetter as was the crotch of her bikini.

Watching her caused me to stiffen and the head of my cock was quickly sticking out the top of my bathing suit. Beth stopped rubbing and pushed her bikini out of the way so she could use her fingers to fuck her pussy. It didn't take her long to cum all over her fingers and when the orgasm subsided, she informed me that she needed my cock inside her. When she sat up, it was to pull the bikini bottom off and before she straddled me, she pulled my swim suit down. She grabbed my cock to guide it in as she straddled me and immediately dropped down taking my entire length.

With my cock inside, she started riding like there was no tomorrow. I could see her lovely 34b tits bouncing up and down as she rode me. Her nipples were rock hard and I used my index and middle fingers to pinch and pull them. I learned quite early in our relationship that nipple play makes her really horny and heightens her orgasm. I caught some movement on the beach and moved my head. " Ah Beth, there's a couple on the beach watching us."

I never in a hundred years imagined she would say " Do you think they would come closer to get a better view? Would it be OK with you if they do?"

My cock had a mind of it's own and I hesitantly said " I guess" which caused her to half turn, continue to ride and motion to the couple to come closer. They didn't hesitate to walk towards us and stopped where they both had a clear view. They were an older couple, maybe mid forties kind of ordinary, the type of couple who might live next door. Beth said" Hi, I'm glad you came over to watch, it makes me really excited to be watched. Oh, by the way, I'm Beth and this is my boyfriend Doug. We're here for a week of fun in the sun and this is some of the FUN."

The couple watching intently as Beth rose and fell on my cock said they were Marie and Don and were also here for a week and this was definitely the most FUN so far. Marie was getting worked up watching Beth and hesitantly put her hand over her pubic mound and started moving her hand up and down and seemed to be really pushing her middle finger into the groove between her lips. It didn't take long before the material was wet. Seeing this, Beth said, "Doesn't that feel good? You should move the bathing suit out of the way so you can really rub your pussy. "

Marie didn't hesitate to pull her bathing suit to the side and exposed her big thick dark brown haired pussy. Prominent lips were on display as soon as her index and middle fingers started rubbing between them. From the look on Don's face, he couldn't decide if he was going to watch his wife masturbate or Beth ride my cock. He was rubbing the front of his suit when Marie push his hand out of the way. She freed his erection and grabbing it with her left hand, started jerkig him off. Don, bless him reached over and pulled one nice sized tit out of each side of the one piece bathing suit.

What a fantastic sight, my naked girlfriend riding my cock, tits bouncing, a complete stranger with great tits exposed and rubbing her hairy pussy while she jerk her husband's stiff cock. Don must have really been enjoying his wife's hand action because he suddenly started jetting ropes of cum which because of where he was kneeling went all over my chest and stomach. Marie was a close second and screamed with pleasure with the intensity of her orgasm. It might have been the second or third wave of her orgasm that caused her to squirt. With each wave, she squirted and now I was getting wet.

The squirting from Marie's pussy and ropes of cum out of Don's cock did the trick and Beth let out her own scream of pleasure announcing her own orgasm. She moaned and screamed as she ground her pussy into my pubic bone and rubbed back and forth. Her actions as well as the sweet nectar flowing from her pussy triggered my orgasm. The intensity was unbelievable and I think there was enough force to it that Beth must have felt it. It was one of the strongest orgasms I have ever had and this clearly was caused by the company and their actions.

Marie and Don were surprised by the squirting because in their years together, it had never happened. I was a wet sticky mess so when Beth got off my pelvis, she bent over and took my soft cock into her warm mouth and sucked and licked to clean our juices off. This caused my cock to swell and by the time it was clean it was erect. Marie was impressed and looking at Beth said, " Would it be OK for me to jerk your boyfriend off?"

"He does like that, you jerk his cock and I'll suck on the knob. Will you be cleaning the cum off his chest first?"

Marie's answer was, "It's Don's mess, he can clean it up. "

Marie grabbed ahold of my cock and started pumping. After a few pumps, Beth's mouth covered the end of my cock and she started sucking enthusiastically. She was going down as Marie's hand went down and back up to march the stroke. The feeling was incredible and I jumped a bit when Don's tongue touched my belly where some of his cum had landed. OK, this was getting weird but, the warm tongue licking up my belly caused a tingle. Weird, but felt good?? Both ladies were rubbing there pussy while they tended to my cock. Looking up I could see the movement of Marie's tits as she pumped my cock. "It would be nice to taste Doug's cum when he shoots sighed Marie."

Beth took her mouth off to say "I don't have a problem with that. Doug can tell us when he's going to cum and you can wrap your lips around the head so you can get it all."

It didn't take much longer before I was warning them that I was ready to cum. Beth's lips left my cock and Marie's lips took their place. Several more strokes did the trick and I was shooting stream after stream of warm salty cum deep into Marie's mouth and she gobbled it down as quickly as she could. Beth let her orgasm be known by again screaming in pleasure. Marie moaned around my cock as she orgasmed as well and again squirted. While getting there bodies back into their suits, Marie and Don thanked us for a memorable experience saying that they would remember it for a long time to come.

They were walking away when Beth started walking towards the water still naked. She didn't seem to be concerned that someone might see her but then again, she just fucked me in front of strangers. I hurried to catch up and then it became a race to get to the water first. I let her win because I love her just that much. In the water, we cleaned up as best we could and raced back to get our towels to dry off. Once dry and back in bathing suits, we headed back to the hotel so Beth could participate in the wet T-shirt contest.

We arrived with twenty minutes to spare and Beth went through the process to enter. She was given a hotel T-shirt and pulled it on over her bikini top. While she waited, she did that woman thing where they reach under their top and remove their bra or in this case, bikini top. Once removed, it went into her beach bag with the towels and sunscreen. Beth took some time to look at the other women with hotel T-shirts to see where the competition might be. While she did that, I was staring at her nipples. There hadn't been a drop of water anywhere near her but two hard peaks were stretching the material and trying hard to escape.

Her observation of the competition left her feeling pretty confident about winning. In her words, one was skinny, one had big tits but had to be at least forty pounds over weight while the others were kind of ordinary and a bit lumpy in the wrong places. There was a call for the contestants to come over by the side of the pool and the crowd of husband's, boyfriends and wives not participating parted to let them through. Four random guys including me were picked to judge. The women lined up and one by one had a bucket of water poured over their chests from behind. Apparently it was cold water because now everyone's nipples were erect.

Now wet, the contestants were encouraged to walk around and flaunt their stuff. Most of the women just walked through the crowd and pass the judge table but Beth was in it to win it and as she walked in front of the table, she lifted her T-shirt and shook her bare tits at us. There were a lot of hoots of appreciation from guys in the crowd who also got a look and it seemed to me that she had just clinched first place. The heavy middle aged woman seemed to want to win as well because as she walked pass the table, she pulled up her T-shirt and bra. Her ponderous tits dropped free and when she shook them side to side, it was quite a sight. There were even more hoots from the crowd. The vote was close but it seems that sometimes size does matter and in this case, big tits got three votes to Beth's two.

I learned something else about Beth after the decision. As we walked away, Beth started to rant a bit. "I can't believe that the big tit woman won! Did you see the big roll of fat hanging over her shorts? How the hell could those guys vote for her? I'm pretty sure that these firm tits and great nipples are a lot better than those big milk tits are"

I told her that I thought she had better tits and if it made her feel any better, big tits husband voted for her along with me. That got a laugh from her and we spent the next half hour or so waking around so the T-shirt could dry. I have to say, there were a lot of guys and even a few women who stared at her nipples which could be seen clearly until the material dried.

We went to the buffet at the other for supper where they made money on the food Beth ate but lost money on me. The buffet consisted of steak, lobster tails, roast beef, pulled pork and corn on the cob. The cobs of corn were cut in two. Beth got her plate and had the server put two lobster tails, pulled pork, roast beef and two pieces of corn on it. I had that as well as a steak. We ate at a leisurely pace and when finished, Beth didn't want anymore but I went back for seconds getting another helping the same as the first. When I finished eating, I went back for thirds and the server shook his head as he filled my plate again. With the plate empty again, it was time for dessert. We ordered coffee and then there was a choice to make, with six choices, it was tough for Beth but I just had one of each.

With supper out of the way, we left the dining area and went to the large room that was used for the nightly performances. The show was great and we leisurely strolled back to our hotel. We chatted about the day and the trip to Dunns River Falls we were going on in the morning. Beth had a new bikini that she had packed and was going to give me a preview when we got back to our room.

Back at the room, Beth riffled through her suit case and pulled out a bikini that was just about the same color as her hair which was good because after stripping out of her clothes, pulled the bottom up and it really didn't hide her hairy bush very well. I guess the saving grace was the near color match but about a half inch of hair was exposed above the top of her bikini bottom and she was going to have to do a little bit of landscaping on the sides. She fastened the top and it fit perfectly. It drew attention to her firm 34b tits and just a hint of areolas could be seen if you looked closely.

Reluctantly we trimmed some hair on the sides but left the strip of hair above with a pair of travel scissors before going to bed. Waking early, Beth walked around the room naked and went out on the balcony to see what the weather was like. There were some appreciative whistles from somewhere below and Beth came back inside with a big smile on her face. "It's another day in paradise!" She said.

We got ready, Beth putting her bikini on under shorts and a loose pink T. We caught the bus with the rest of the tourists and were on our way to the falls. Once we arrived and got off the bus, Beth removed her shorts and T which went into the beach bag. I took my time rubbing sun screen on her nearly naked body, enjoying every minute of having my hands on her lovely body. We had a great time at the falls as did everybody else. Returning to the hotel, when Beth removed the skimpy bikini the contrast of colors was startling. Her previously covered areas were white while the exposed skin was bright red. She donned loose shorts and a pink T so we could go for supper.

We had a quick supper and went looking for a store to buy some moisturizing lotion to possibly lessen the effect of the sun burn. We found what we needed and headed back to our room where I was going to apply it to all burned areas. ( Am I a lucky guy or what??) Beth stripped and laid on her back on the bed so I could apply the lotion. Squeezing a handful, I started at the front of her shoulders and worked my way to her toes. The lotion was cold but I don't think that was why her nipples stiffened and they were soon just as erect as I was. As I worked the lotion into the skin above her tits, I took the time to pinch each nipple which caused her to moan a bit. I worked down and while rubbing lotion on her stomach she spread her legs just a bit and yes, the hairy bush was starting to get wet in the middle.