My buddy's gf takes my virginity

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My first time. . .and with my buddy's girlfriend.
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This story is from my college days. I was going to school at a little church college on the North Shore of Oahu. I won't name it because this isn't the right place or time to bring in religion, but many of you may know the college. Anyway, I had set my sights on this 19-year-old freshman girl named Kate (of course I changed the name). She was out of my league, but she was a freshman and I was a Junior and I figured if I got to know her before the other guys discovered her than I might have a chance.

Kate had super long brown hair that went past her waistline. She was part el-Salvadorian and her skin was a dark golden brown. She had a tiny waste, a round athletic butt, and full breasts and a smile that melted me. Honestly, I couldn't find a flaw in her figure or her face. I was infatuated.

As for me, I was a casual surfer through high school from San Diego and continued surfing through my days in college in Hawaii. However, in college I also picked up swimming and weightlifting for exercise. I was swimming 3 days a week and lifting weights the other two days and surfing in my free time. I was in good shape in high school, but any softness I did have was melted away in my wonderful Hawaiian lifestyle.

My problem was that I was a really nice guy. I had no shortage of girls interested in me, but I was insecure and naturally very shy, and I would get moved very quickly to the "friend-zone". I was told often how good looking I was (and looking back at pictures they weren't lying) but that I was just too needy and too nice. Ugh!

So I started asking Kate out on dates. She accepted enthusiastically and we started going out often and became very close friends. Being my terribly insecure self, I didn't have the courage to make a move on her and so by the fourth date the closest I had ever got was to put my arm around the back of her chair. But. . . she kept saying yes, and I kept asking her out. After a few weeks we were hanging out between classes, eating lunch together, and we had become best friends - all without me making a move.

I had blown it. I had once again moved myself into the friend zone. Years later she had confided in me that she was more than ready to move things forward, but I had given her clear signs that I was not interested in her in that way. Ouch! The problem had been I was TOO interested in her and the fear was just too great. We hung out nearly every day on the beaches and she would watch in her tiny bikini while I surfed -- all the benefits of a hot girlfriend without any of the physical benefits. It was pure frustration.

Most everyone in the school thought we were a "cute couple" and she and I had to keep telling people that we were not dating (again ouch!) -- we were just close friends. Our reputation as a couple was so complete that neither she nor I could get a date without reassuring people that we were not a couple.

Six months later. . . my best friend Joe (again, changed the name) joined me at the college and moved in as my roommate. We were both 22 years old and Juniors, with one year left until graduation. My torment was complete when I introduced him to my friend Kate and within two days of hanging out on the Hawaiian beaches, they were making out feverishly in the sand. Kate in a tiny bikini that barely covered her tan body and Joe in his swim trunks.

I still remember watching him stand up and stretch after that first make-out session and seeing his erection protruding like a flagpole through his shorts. I knew that she had to have felt him pressing against her stomach and I felt the knife of jealousy take an extra deep twist in my gut. I had wanted to press myself against her just like that for the past six months and now that hope was gone.

Kate and Joe quickly became an item.

Now that the pressure was off and I was no longer constantly afraid of blowing it with her, she was very free with her hugs and touch, and even friendly kisses on the cheek. Joe was her boyfriend, but in many ways, I was still her best friend -- the one she came to for support. She and I grew closer without the threat of a relationship in the balance. I was finally able to open up to her and tell her how I felt. Joe already knew how I felt because he knew I had been trying to get together with her even before he became my roommate.

I went through a period when I refused to go out with the two of them (both my best friends) because of the intense jealousy. They agreed to cut down on the making out in front of me and I went back to being a third wheel.

About this time, Joe bought a very old and beat up CJ-7 Jeep. The Jeep had no doors and no top and was the color of rust from top to bottom. It drove like a tank. It was loud and windy and perfect for our island lifestyle -- and it only had two seats. This gave us the freedom to surf up and down the North Shore and weekend trips to Honolulu to play at being tourists or to see a movie.

I tried riding in the back with the surf boards and gear, but that was super uncomfortable. Kate offered to take turns riding in the back, but I was way too much of a gentleman to be comfortable with that. So, we compromised on having Kate sit on my lap while Joe drove (I'll come back to this).

I should mention that Kate was not perfect. She had one huge flaw -- she loved attention. Along the way, Kate had begun to tease me by showing off parts of her body. For short or occasional trips most surfers spend the day in their swimsuits. However, when it is your daily lifestyle you learn that it is nice to rinse the sand off and put on dry clothes. Otherwise, you would spend literally every day in a wet swimsuit.

Joe and I are from San Diego, and we had always changed under a towel after a day at the beach (which now was everyday) rather than finding a changing room. For the boys it was easy, but for Kate it was a stretch to cover everything at once while taking off her wet bikini. Kate would "accidentally" drop her towel and give me a flash of her full incredible breasts, or she would raise her hands up to tie her hair with her back to me -- giving me a brief glimpse of her butt cheeks.

It's amazing -- I saw her ass cheeks and tits in a tiny bikini nearly every day but there was still something incredibly arousing about seeing the same breast without the little piece of cloth covering the nipple, or the same perfect round ass cheeks defying gravity without the thong lacing down the middle. It was naughty and forbidden and it drove me crazy.

I think the first time she flashed me her tits might have been an accident, but seeing my response encouraged her. Soon, it became a daily game she played. Joe noticed her flirting, but he wasn't the jealous type and thought it was funny. I think he felt bad that he had taken the girl I was after and so he had made it ok in his mind for her to flirt with me as a consolation.

Joe and I would change to dry shorts and Kate would remove her wet top and replace it with a loose-fitting t-shirt or tank top. I loved how her side-boob and upper torso showed through the tank top and her perky nipples stuck out through the cloth.

Back to the Jeep. So, there I was. Seriously lusting after Kate when my best friend swoops in, steals her in a matter of days, buys a jeep, and suggests that Kate sit on my lap while we drove around in almost no clothing. Is this starting to make sense?

Let me just get this out there. . . there was not a single drive we took that I didn't get mostly erect while she sat on my lap. The first time, she plopped down on my lap in her bikini and at least acted like she had no idea what affect this would have on me.

There was nothing but a chain where the door should have been, so inevitably my right hand came to rest on her hip with my elbow on the chain. She then pulled the seatbelt (lap belt only) across the both of us and handed me the end to click in place. Her smooth naked skin of her hip bone under my hand was too much for me and my cock began to grow.

After a minute of engorging it was painfully hard against her crotch and I was mortified. We had not even left campus yet and the three or four huge speed bumps were causing me way more pleasure then they should have. By the time we reached the end of campus I was being pinched by the cloth and I had no choice but to reach under her bum and force my cock to one side of my swimsuit seam.

There was no hiding it from Kate and she delicately lifted her bum as I pushed my shaft to the left side. My swimsuit was loose fitting and once my cock was running down my leg it was much freer to stick up then it had been all scrunched up in the middle. I thought I would die of embarrassment and I almost stopped at the edge of campus and asked to be dropped off.

This is when Kate leaned back into my stomach (which actually took some of her weight off my stiffened cock) and leaned her face back to talk into my ear.

Kate giggled and said, "I think it's cute."

With those four words I became even more erect and nearly shot a load. For that trip at least she sat still and we both spent the rest of the trip pretending I wasn't pushing hard against the entrance to her pussy.

By the fourth or fifth week of this we had grown very comfortable with the situation. I had even told Joe several times in our late-night talks in our dorm room that he could not expect me to have Kate sit on my lap and not get turned on. It just wasn't possible! He agreed and laughed it off.

One time he went as far as saying, "Well, I feel like crap for stealing her from you, so I guess enjoy it."

Ok, in my head that was all the rationale I needed. I began to enjoy it.

During this period is when Kate began to flash me her body and flirt with me. She was trying to get me nice and turned on for our drive back to campus. She would sit on my lap and wiggle just slightly. I know it sounds strange, but it even became normal for her to wait until I got hard and then she would lift her bum while I adjusted my length to one side or the other.

I also started choosing the thinnest and loosest shorts I owned to change into for the drive home. Joe would play reggae music and Kate would give me a very real lap dance as she grooved down the Kam highway. Her hair was everywhere around my face unless she tied it up. When she wasn't dancing, she would lean back into me and lay her head against my shoulder.

Eventually we were comfortable enough that I began to explore the side of her body with my hand. I would tickle her on the inside of her hip bone just to make her squirm against my cock and run my hand caressingly inside her shirt. I dared only to go from her outer thigh to just under her right breast -- sometimes feeling the weight of it before I would chicken out and rest my hand again on her hip.

One summer afternoon (the North Shore has very little surf in the summer) we decided to make the hour drive to Hanauma bay for some snorkeling. Most of our drives around the North Shore were short 15 to 20-minute drives and so things between Kate and I could only go so far. If we did go longer, we were usually fully dressed for a trip to Honolulu.

This was a full hour each way in our swimsuits. We got there without anything crazy other then I learned that even with the hottest ass on you lap, an hour is a long time to keep a hard on. My erection would come and go and at times it was a little uncomfortable.

It was a hot summer day and we were sweating without air-conditioning and anxious to get in the water for some snorkeling. Kate decided to wow the tourists (and us) with an extra skimpy white bikini. It was so thin that it was mostly see through when it got wet. She looked amazing and constantly turned heads with her full round breast and amazingly cute tanned ass. She had the slightest hint of a tan line where her normal size bikini usually covered.

Joe and Kate definitely broke their self-imposed rule of not making out in front of me. They spent a good deal of time rolling in the sand grinding on each other. They were obviously both very turned on and wanting to be alone. I couldn't blame Joe; she was a stunning 19-year-old in her prime and she was oozing with sexuality.

After a day of snorkeling we decided to head back. It was nearly an hour to the nearest restaurant, and we were all starving (having only brought sack lunches from the cafeteria). We all changed into our comfortable driving clothes -- Kate putting on a loose-fitting tank top with huge holes cut out of the side to show an ample amount of side-boob as well as a glimpse of her torso. As usual, she removed her bikini top but left her bikini bottom on under the shirt. I put on a thin pare of loose shorts with an elastic waist band and left my shirt off for the drive home.

As we reached the top of the climb up from the bay, we all stopped to use the restroom and found the jeep in the parking lot. Joe took the bag of snorkeling gear back to the restroom so he could rinse off the saltwater and Kate and I waited in the jeep. I got in and Kate surprised me by climbing in to sit on top of me.

I thought it strange that she would want to ne on my lap while we waited for Joe to get back, but it was a steep climb to the parking lot, and I figured she just wanted to sit down. She sat on my lap without the seatbelt and began a slight motion with her bum -- moving forward and back just enough to get my attention.

After watching her make out all day I knew she was horny and at that age, my cock was always ready to go. Being alone with her and knowing that it was not "required" for her to be sitting on me, made it that much more arousing and I was stiff in an instant, my cock was sensitive, and my balls were aching for a much-needed release. After just a few minutes I went from looking forward to the drive to desperately wanting it over with so I could go home and take care of business by myself.

After sitting on my lap just long enough to get me hard, Kate decided to get her water bottle out of her backpack in the back of the jeep. She rose off my lap and bent between the seats to dig for it, leaving her ass hanging invitingly in the air beside my head. Since Joe was not back yet, I didn't even try not to look.

I turned my head to the left and I was staring point blank at her white (still wet and see through) thong hugging to one side of her pussy lips. The seam on one side was up inside her and the tiny space of material between the two seams was covering her right pussy lip. Her loose tank top was hanging open and I had a clear view all the way up her shirt - passed her flat belly - to her perfect round titties hanging like ripe fruit.

She found her water bottle and before I could look away, she looked back at me through her shirt and smiled upside down at me -- knowing that she had just caught me admiring her nude body. As she backed herself up and started to return to the seat, my cock was standing at full attention in my loose shorts. I couldn't even keep it down along my leg without physically holding it with my hand. There was no way to conceal my 7 and half inch erection (hey! When you are 7.5 inches you claim every half inch!).

By this time, Joe had reached the back of the jeep and was stowing the snorkel bag. I quickly grabbed a towel from under me and settled it in a clump on my lap to hide my erection. Kate stood up straight in front of me, her toned ass right at my eye level and was turning her upper body to talk to Joe as he finished putting the gear away. I could see her thong was still off centered as it traveled up her crack.

She then reached down and picked up the towel and stared directly at the tent pole that she would soon be sitting on. She positioned herself carefully and slightly spread her legs as she deliberately lowered herself onto my stomach, letting my cock find its way to settle comfortably between her legs so as to not crush me. Then, she settled the towel over the two of us.

I reached down to adjust my cock -- to make sure it was fully to the right side of the seam in my shorts, but she wasn't giving me the space I needed. She was in a horny mood and being horny kind of made her a brat at times. Instead of lifting her bum she scooted back and forth an inch or two to tease me.

The problem was that I was so hard that it hurt to not be positioned right. Without thinking I grunted, "owe" under my breath and pushed on her bum a little to get her to lift up for a second. She still refused to budge.

As Joe was starting the jeep and backing out of the parking stall, Kate asked me, "What's wrong?"

I replied close to her ear, "Nothing. I just got pinched a little by my clothes."

With this she lifted her bum a few inches off my lap and reached her hand down under the towel and between her legs. In one motion, her hand slipped inside my waistband, grasped the base of my cock, and slid her hand to the end so that my cock was free of my waistband. She deftly tucked the waistband under my ball sack before she sat back down and asked, "Better?"

I sat speechless as I felt her settle back down with my bare cock now thrusting up between her naked inner thighs. Had the towel been moved my tip would have been visible thrust firmly in front of her pussy.

Before I could really process what had just happened -- and that I would be spending some time like this, she handed me the end of the lap belt and I buckled it in place. Joe had turned on the music and was pulling out onto the main road. We sat like that for about 5 minutes, both of us trying to ignore the fact that my cock was nestled against her outer lips underneath the beach towel. I could feel myself pulsing involuntarily and for a few minutes I tried to think about old grandmas and camel poop and anything that might take away my erection.

Just as the newness passed and I was starting to feel like this escalation of teasing was progressing from fun and daring to a sort of condescending mockery (after all, this was destined to end with me being subjected to a whole new level of frustration) I felt a tickling on the head of my cock. Apparently, the temptation to "play with it" was too great for Kate and she was running one of her long nails up the underside of my cock.

I gasped involuntarily as my nerves caught on fire and my cock started pulsing with renewed sensation. First one nail, then I could feel the underside of my shaft being lightly scratched with three or four of her fingertips from my scrotum to the head of my cock and back down again. Slowly, like she had all the time in the world and nothing better to do.

She lightly caressed up and down for several minutes while my mind raced, and my heart beat so hard I knew she could feel it against her back. Her hair was flying wildly in the wind so I gathered it up and pulled it all to the left side of my face and tucked it between our bodies. With her hair obstructing any view of my face from Joe, and with intense pleasure being agonizingly fed to me through her caresses, I bit her neck -- maybe a little too hard. In response, she squeezed my balls as a message that my bite was too hard.

Before long, I was oozing pre-cum in what seemed like a steady stream and she used this as a lubricant to gently circle my cock head until it would get a little dry and sticky. She would then grab my shaft and massage and caress until I dripped more lubricant out before switching back to gentle lubricated swirls. On and on, milking me of precum to be used as a lubricant.

This was truly my first experience with edging and it was frustrating and luxurious and intense. It made me feel like a beast. I wanted to ignore everything but the need for sex. I wanted to throw her down and ram my cock into her and demand the release from the pain of such intense pleasure. I wanted to own her and claim her by shooting her pussy full of my seed. Needless to say, I had a torrent of uncontrolled thoughts while I sat their helplessly as she gently stroked my cock and none of my thoughts were politically correct.

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