10 day Fling in the Holy Land Part II (MF) | 2016

PART I

This is my first post, and also the first part of this story. A little bit about me: 5’6”, 135 pounds, short brown hair, electric blue eyes, in pretty good athletic shape from years of sports and fitness This all begins a few years ago when I was wrapping up college at a large public university in the South. I had accepted a job starting later in the summer and I was graduating in early May. I thought it would be a perfect opportunity to travel a bit before I was locked down by the working world. I was 21, the world was my oyster but I was a bit short on cash. Therefore I decided to apply for a Birthright trip, which is a free 10 day trip to Israel for anyone between the ages of 18 and 26 who was born Jewish. Birthright trips are known for highly encouraging hook ups between participants, and you are spending close to 24 hours a day with the same 40 people so things can escalate quickly and get awkward if not played perfectly. I was eventually accepted onto a Birthright trip and was told to be at the airport to meet my group at 9PM on a certain day in May. The flight was to leave at 2AM so we would have plenty of time to bond with our group before takeoff. The trip I had been given a spot on was for 18 to 22 year olds. As the day finally approaches I get dropped off at the airport and am one of the first ones there. I eventually find my group and check in. More and more people arrive and after an hour or so most of us were there. Obviously I had been checking out the girls as they arrived to see who was the prettiest and who I would try to go after. When most had arrived we went through security and got to our gate at the airport and unfortunately there didn’t really seem like there were too many options as far as the girls were concerned. I spent most of my time chatting with a few guys I had met, Matt and Dave. Matt was from a large private school in New York and had just graduated as well, and Dave had just finished his freshman year at a school in Canada. As we had been talking for a while I see two pretty attractive girls out of the corner of my eye looking for a group. I watch them over Matt’s shoulder for a few minutes and they seem to be putting their luggage with our group. They put their luggage down and immediately go to the bathroom. When they returned I saw them just standing by themselves talking away from the rest of the group. I took this as my chance to introduce myself. I skillfully slipped away from Matt and Dave and confidently strode up to the two girls. I asked them if they were on the trip that I was on and they said that they were. I come to find out that their names are Kathryn and Marissa. Marissa is about 5’4” with straight brown hair down to the bottom of her boobs, green eyes, a tight little ass, probably 120 pounds as she was quite thin and large boobs that she concealed well that were about a D cup. Kathryn was about 5’5” with nipple length brown hair that was straight with a little bit of a wave, hazel eyes, also about 120 pounds, with curvy hips and a really nice ass sculpted from years of horseback riding, with small boobs of a small B or big A cup. I was talking to them for a while and find out they are both from Boston and became friends at college and had both just graduated. I seemed to be holding their attention well and getting some laughs out of them, when I see Matt and Dave coming on over. They enter the conversation and a graciously introduce them to the fine young ladies I had just met (easily the most attractive two girls on our trip from the looks of it). We continue talking for about 15 minutes until our group leaders start doing some dumb ice breakers with the whole group, in the airport mind you. After the ice breakers are over Matt catches me to talk for a minute and mentioned that him and Dave were watching me closely and were impressed at how well I seemed to be entertaining Kathryn and Marissa. He said that he wasn’t sure if him and Dave should have come over and I said it wasn’t a big deal and that everyone was fair game at that point and we were all getting to know each other. We boarded the plane and headed to the Holy Land. I had lost Marissa and Kathryn in the fray and didn’t see them again until we were in Israel. When we arrived, we were quickly whisked away on the bus to our hotel as it was already approaching midnight. We get there and everyone turns in for the night with their 1-2 other roommates (of the same gender. The next day we spend doing hikes and various tours, and I kind of pair off with Kathryn and spend most of my day with her and Matt and Marissa kind of pair off as well. That night our guide lets us know that we are going out to a bar so we all get dressed up to go out and meet in the hotel lobby. Kathryn comes down looking stunning, wearing a black lacy top that exposed her stomach and most of her back as well as some tight dress jeans and black shoes. We walk to the bar and our guide tells us that since we are all new friends we all have to buy someone else a drink. I find myself with Matt and Dave again and we all buy each other drinks and chat about our various options for girls. After a bit we find Marissa and Kathryn and start dancing with them. They laugh at how into dancing I get and after a while I convince Kathryn to buy me a drink. We go to the bar and the bartender brings over two beers one of which clearly is more full than the other. Kathryn gives me the one with less in it. “You screwed me!” I exclaim at how she ended up with more beer, and she smiles flirtatiously. At this point I was a bit buzzed. With a nod and a smile I quietly add: “And it won’t be the last time on this trip.” She feigns shock at this and mouth agape hits me on the shoulder and says: “Yeah right.” I had been hearing rumors that afternoon so I straight up asked her if she had a boyfriend and she said yes . They had been together since her freshman year in college so about 4 years. This was a deterrent but I had to go based off of how she was acting not what she was saying, and she was being very flirty with me. We spent the next day touring Israel and swimming in the Dead Sea and opening up to each other and I come to find that she is not happy at all in her relationship and they are likely going to break up soon, as she is no longer really physically attracted to him and mentions that the sex sucks. That was Thursday and we were heading to the infamous Bedouin tents that night. For those of you that don’t know the Bedouin tents are where all 40 of us would essentially be sleeping under a tent in the desert in sleeping bags. Perfect opportunity for hook ups. Of course Kathryn, Marissa, Matt, Dave, and myself all find a corner of the tent to lay our sleeping bags down. I strategically position myself next to Kathryn. The 5 of us spend much of the night quietly whispering, and eventually everyone falls asleep except me. Or so I had thought.

PART II

As I lay there in the middle of Israeli desert listening to 40 late teen/ early twenties humans sleeping/snoring/breathing I feel a nudge at my feet. I get my bearings and try to figure out what it is. I wasn’t entirely sure but Kathryn was right next to me so I thought she may be trying to play footsies with me. I gently nudge her legs back. Then a second later I feel some pressure coming back from her legs. Mind you we were in sleeping bags so it was tough to feel much. We nudge each other back and forth a few times and inch our heads closer and closer together until our faces are mere inches apart. She whispers I need to talk to you about something. I ask her what it is and she does that classic girl move where she smiles and says never mind. I had an idea that it was that she liked me and wanted me, but I wasn’t going to be the first person to say something as she had a boyfriend. After a while of silence we both fell asleep. I was getting frustrated that nothing had happened yet as this girl was teasing me beyond all measure.

That day we went on a long hike at sunrise and rode camels in the afternoon. The entire day Kathryn and I spent flirting. That evening at about 2PM we checked in to our hotel for Friday and Saturday night. We immediately headed for the pool and Kathryn was the show piece of the afternoon looking beautiful in her two piece skimpy bikini. As the sun drew near setting it was time for Shabbat services and dinner so everyone got reasonably dressed up for the evening, guys in button downs and khakis and the girls in nice sundresses or what have you. Kathryn and I sat next to each other playing with each other’s hands most of the time. After dinner we were all sitting around outside the lounge of the hotel and people trickled away one by one to smoke or to hang out in each other’s rooms. Eventually it was down to Kathryn, myself, Matt, and Marissa. Kathryn mentioned that she was tired and I offered up a neck massage. I have had a lot of practice over the years and like to think I am quite good. So I sat on a ledge behind her as she sat on the ground and I started gently but firmly massaging her shoulders and neck. After a few minutes she was like putty in my hands with her head hanging listlessly as I gently massaged her scalp and neck. She loved it. After about 15-20 minutes I told her it was my turn and we switched for a bit. Later that night, Kathryn and I decide that it would be funny to take Ambien and try to stay up and see what affect it has on us as we had heard it was equivalent to getting high. We take the pills and within minutes we are loopy. She decides this is when she wants to tell me what she was thinking of the other night. She says she likes me and likes being around me but has a boyfriend and does not want to cheat. I said I respected that and would only do what she wanted. She was lying on her bed and I began rubbing her back. I eventually straddle her perfect ass and rub her back some more. At this point my cock is hard as a rock and quite obviously pointing out of my shorts. I lay down on top of her so she can obviously feel my cock against her ass. Then she starts grinding her ass into my cock. Slowly and rhythmically at first and I begin thrusting back in her rhythm.

“You like that?” I say

“Ugh Yes” she moans

“Yeah I bet you fucking like feeling my cock against your ass like that” I reply.

We begin grinding more and more until my cock is rubbing against her pussy as it has by now jostled its way through the slit in my boxers and through the slit in the shorts I was wearing. She still had her shorts on but was obviously enjoying thins by her moans. She seems to be getting close to orgasming when she sits up and says that we can’t be doing this because she has a boyfriend. Meanwhile we are still a bit loopy on the sleeping pills and she finds my bare cock with her hand and begins stroking it. She says that we have to stop, so we do. Then a few minutes later she seems to have changed her mind and we get into the same dry humping from behind position that we were in before. She again gets close to orgasm when I hear the latch on the door. I immediately sit up and pretend to just be giving her a normal massage. Her roommates are obviously a bit wary of what was happening and I quickly dismount and say goodnight and head to my room for the night, extremely sexually frustrated.

The next day we spend the entire day relaxing at the hotel, by the pool, playing Frisbee you name it. That was also the day we met the 6 Israeli soldiers that would be joining us for the last 5 days of our trip. Kathryn and I rubbed suntan lotion on each other and did not speak of the previous night. That night we headed into the little town there and went to a bar and restaurant to hang out. I got a bit buzzed and on the walk back to the hotel Kathryn and I were holding hands and walking with Matt and Marissa who were also holding hands. Once we get back most people head up to their rooms to go to bed but several of us continue to hang out. Somehow Kathryn and I find ourselves alone wandering the property under the beautiful moon. We stroll with my arm around her waist for a bit until we are in a really secluded area. I’m not sure how it came up but I said that we should dance! I put on the sexiest slow song I could find and she agreed to dance. I slowly twirled her in circles and we danced with our bodies pressed up against each other, cheek to cheek. Every once and a while we would both look into each other’s eyes and she would smile at me and laugh. After the song was over I turned her around so her back was against my front and my hands were on her hips and we gently swayed back and forth as she felt my bulge growing against her ass. My hands slowly find their way up her dress to her small perky tits. I begin gently massaging and caressing them and she moans into my neck as she tilts her head back. I slowly peel each of the straps of her dress off and gently rub her small pink nipples as they begin to harden in the brisk air. I continue massaging her boobs for a few minutes until she turns around and again says that she doesn’t want to do it as she has a boyfriend. I again say that I understand and won’t do anything she doesn’t want. We continue walking around the property and she says she’s getting tired and wants to turn in for the night. I acquiesce and we begin heading toward our rooms. About half way there in the middle of the property she tells me we can’t do this anymore and that that was it. I said that I understood even though I wanted more. She said that I can have one kiss and to make it a good one. We turn and face each other. We both laugh and admit we have chapped lips and we both take an awkward second to wet them. Then I grab her lower back with one hand and her face with the other hand and slowly guide her towards my face. I lock lips with this beautiful girl who had been teasing me for days for the first time. I give it my all and make sure she enjoys it. We make out for about 2-3 minutes and she pulls away with a mischievous smile. Ever the tease she pulls me forward by my waistband pulls my waistband out and grabs my cock and tucks it into my waistband.

“That’s how you get rid of a boner right? The Texas Tuck” She says slyly.

“You are such a tease Kathryn” I say with a smile as she darts away as I feign chasing her.

At that point I was happy it had gotten that far. I was elated to have this gorgeous girl kiss me and touch my cock but I was hungry for more. I didn’t think anything else would really happen after that but boy was I ever wrong about that.

To be continued…

Any feedback is greatly appreciated! :) pics (regular and nudes of her) are to follow in the next piece