Handjobs to Orgies

** Authors note: This is a true story from my experience and I hope you enjoy. I hope to post another three or four stories over the next few months that detail other chapters of my life. I would love to receive feedback on whether you liked it or not... or whether it at least got you hard or wet! All questions are also encouraged, I can fill in details I missed in the story and chat more.

Enjoy! **

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It is summer in the late 2000s, college move in at a Texas campus. As per Texas in the summer, it is very hot with thousands of students trying to cram into the dorms. I, Phil, am headed into my dorm and enjoying seeing all the sexy and cute girls headed into the dorms also. Over the next few weeks I get all settled into dorm and college life, classes start and friends are being made. A group of ten of us in the dorm had started to become very good friends, hanging out until 5am every night either in the dorms or out around campus.

From very early on there was a girl in our group who caught my eye. She had lightly tanned skin, 5'3", in great shape (high school soccer player). She had an awesome butt and nice B cup boobs. Her name was Ashley and she was the catch of my eye from the beginning.

A few weeks go by and I finally decide to ask her on a date, which as a college freshman consisted of going to one of the restaurants right off campus. Pretty unspectacular but it did the trick. A few late nights and we decided to date. We exchanged sexual history, hers was very mild. Consisted of a couple boyfriends and making out.

There was one exception which was a night her senior year where she gave her first to a guy she was not dating and followed it up a few hours later with a BJ to a different guy.

My history was also mild with a little more action, a few girlfriends where we gave oral to each other was about it. Both were virgins and neither had a ton of experience.

As our college "dating" progressed so did our sexual appetite for each other. It only took a week for us to go from small kisses to making out to handjobs and fingerings and then to oral.

A few notes at this stage to make it a little more detailed: as she is a small girl with toned legs and butt, her pussy was absolutely lock tight. She kept it shaved and clean. She had only been fingered a few times total so very few things had even found their way into her. As for me, I am a 6'0" white male, in shape who played sports all through my childhood. And I had the big package that is seemingly so coveted. It isn't a monster, but a solid 7.5" and very thick with a big head and slight upwards curve.

The first time I licked her pussy she squealed with joy, she had never had it before and by that time we had been making out and playing for a while. She had on a little pink thong and I knew it was time for her to lose oral virginity. As I fingered her under the thong I had slowly worked my tongue around the thong, gently licking her pussy lips before finally sliding her soaking thong aside and licking up and down her pussy. After a couple seconds if that I reinserted a finger deep inside her and licked her clit until she came the hardest I had ever seen.

She writhed in joy and my rock hard cock was almost as happy. She quickly yanked out my cock and sucked me dry in a matter of minutes.

From there we were off to the oral races. Not sure a day went by where we did not 69 at least twice. Her (HOT!) slutty roommate walked in on us a few times and always laughed as Ashley was on top of me sucking my cock while her pussy was buried in my face.

And as you can probably guess, a few weeks later we started discussing ending our virgin status. A few days later we set a date night which we planned to end in sex.

We get to the night, have a nice dinner and head back. She was wearing a pair of tight white jeans, a low cut shirt and some jewelry. When she bent over I could barely tell she had on a little black gstring. I was ready.

We got back to her place, had a glass of wine and cuddled up. As with nervous expectations, I had her topless just in her black gstring within minutes. My cock was rock hard from the minute we walked in. We were making out, sucking on her boobs, then she grabbed my cock through my boxers and started stroking.

There were a few moments where I was worried the fun would end WAY prematurely but fortunately it did not. I moved my hands down and rubbed her pussy from outside the gstring, it was so small and she was so wet that it was mostly just pussy I was rubbing. Hardly a need to pull it aside. Pretty soon I moved on down and started licking all around her pussy as I was fingering her, first one finger then two. I could tell she was going to cum soon, which was not the plan, so I moved up to kiss her and as I did so my bulge pushed up against her pussy. As we kissed she pulled out my throbbing cock and I gently slid it in.

The first sensations were so amazing as my head struggled to find space. As I mentioned, she was very tight so my thick cock was a very tough fit. It took us five minutes or so to get me halfway in her and then a few minutes later she begged me to go balls deep. As I thrusted every inch into her she let out a scream and came at the same moment. I did not last much longer as I started pumping her with long full strokes. She was already on birth control so as I released my entire load deep in her we both collapsed in total joy.

Over the next few months we fucked like bunnies, trying new positions as she got used to taking my size. She was small so I was able to manhandle her and fuck her against a wall or on a chair or in the car. Her freak side was really starting to come out. We start going to adult stores and buying vibrators and dildos to play with. She bought dozens of thongs, gstrings and sexy bikinis to keep me humming.

At some point we started adding anal to the rotation, her ass was just too much to resist during doggy style. From there I would add a dildo in her pussy while I was fucking her ass. She seemed to love being filled like that and loved to hear me talking about how she is double stuffed with two cocks. Every few days we would bust out the toys and find a new way to fuck, whether in a swing or with a big black dildo. It also became more and more frequent for me to wake up in the middle of the night to find her with either a vibrator or dildo pleasuring herself. She had really turned into an absolutely naughty college girl.

The summer before junior year we were still dating and decided to take an international vacation to Spain. We would go to Madrid, Barcelona and then end it on Mallorca. We go on our trip and everything goes as you would expect, sight seeing, fucking in hotels, sight seeing, drinking, repeat.

Our first taste of what was to come came in Barcelona at the hotel pool and sauna. At the pool a woman came in and swam, but when she undressed she had on a thong bikini and the top came right off. She swam around topless in a thong with us for a while. Neither of us could really believe it and Ashley told me a few times how sexy that was.

We traveled into the sauna after that and before long a mid 30s couple joined us, except they had no clothes on whatsover. They were both fit, in their late 30s or early 40s, from Germany and seemed nice. He had a nice long uncut cock swinging around and she had a good looking set of fake Ds along with a well shaved pussy. Both were blonde and tall and definitely attractive.

We both just sat there in silence and silent awe for a while. At one point I had the opportunity to recommend to Ashley that she go topless which she eagerly did. After 15 minutes we departed and headed back upstairs chatting about how open people are and how hot it is. Obviously this ended in a fantastic fuck session complete with my cock in her ass and her favorite dildo that we brought in her pussy.

We traveled on to Mallorca for our last stop to hit the beaches and relax. We checked into the hotel around 3pm and hit the beach with drinks in hand. Immediately we got a taste of what we saw in Barcelona, thong bikinis and topless women everywhere. Even a few guys in way too small Speedos. We both just enjoyed taking in the beach, view and lack of clothing.

A few more drinks in and we started talking about the absolute lack of appropriate bikinis Ashley had brought. Way too much coverage for this place where we know nobody and less clothing is very acceptable. We headed into town and hit the first store we found and purchased a number of skimpy bikinis. None covered hardly any ass and some even outlined her pussy beautifully when wet.

We hit the beach the next day, her in a little blue thong bikini and top. We started drinking, played some games and hanging out. Eventually we decided to take a stroll down the beach once it got a little crowded. As we got further down the beach we noticed a sign that had pictures indicating no clothes. We looked at each other and decided to go for it. We ran back and grabbed our things and headed back.

When we entered the nude area, it was like another world had opened to us. Boobs, asses, cocks and naked bodies everywhere. Small, large, old, young, everything. We found a place on the beach and set down our things and laid out. She initially removed her top, letting her nice boobs spill out to the world. After a few minutes of nervous hesitation I started to pull my swimsuit down and she gave me a sly grin before undoing her thong bikini. And there we were, both naked and surrounded by other naked people.

A few uneventful hours went by until a single Italian male came and put his things down about ten yards in front of us. He was mid-late 20s, about 6'2", good looking guy. After he put his things down he lowered his swimsuit and what had to be a fake cock fell out between his legs. His back was towards us but you could see it hanging below his butt between his legs. A moment later he turned around to sit down and it was an easy 7-8" flaccid, just swaying side to side. We both muttered a sound of surprise as he sat down faced towards us. In that moment I knew something needed to happen.

I had considered a 3some with another guy before but had no idea how it would ever happen. It all came back to me and I was horny and curious to see where this would go.

About 30 minutes later it was time to reapply sunscreen. After lathering each other up, I told Ashley I needed to get around her pussy also. I asked her to spread her legs and she did. She was now sitting down with her legs spread in a V facing the Italian. He was sitting reading a book, his cock flopped over his leg. I made sure to get to her side as I applied sunscreen around her inner thighs and pussy so that he had a good view.

I went slowly and could feel her wetness as I rubbed it in. As I was almost done I looked over and he was no longer reading a book or completely soft. His cock was slightly raised as if in salute. Ashley had her eyes closed enjoying the gentle rub and so I continued going back around her legs and up to her boobs. He was getting harder and harder. I finally got the courage to wave him over to us and he slowly got up and walked over.

I finished and Ashley opened her eyes to see me sitting on one side and him on the other, both of us slightly hard. We did some quick introductions and made awkward small talk. It gradually got a little better and we all got more comfortable sitting together, her in the middle.

I could tell she was all on board now as she was clearly flirting with him and so I decided the guys may need some sunscreen where it had been missed earlier. I squirted some on my cock and passed it to Emilio who took my cue and did the same. She stared at me before starting to rub it in and asking me if we could do this here. I assured her it would be OK, not that I really knew. We were somewhat at back of beach and it was not packed at all. After she quickly rubbed mine in (now that I was very hard), she stopped and started to wipe her hands off. I quickly reminded her that his was not done. She gave me a little hesitation before a slight grin and turned to him.

He was already mostly hard by this point, and when she saw it she audibly said "oh my god" as his cock was flying at least 9".

It wasn't the thickest cock ever, or even as thick as mine, but it had the length. She lightly started rubbing it in as he got to full length, I would guess 10" of hard Italian cock. It was uncut and had a nice, unveiny shaft that stretched forever. Within a minute or two she had switched from rubbing in sunscreen to stroking his cock head to base. Her hand looked tiny on his shaft but she worked it well. Before long she added her other hand, turning her back to me and slightly spreading her legs. She was double stroking him as he moaned in pleasure.

I took the opportunity to run her pussy discreetly and snuck a finger inside her soaking pussy. As she went hand over hand he exploded, shooting his cum high in the air for a few seconds before covering her hands in the rest.

From there, it only gets better. We of course had some very awkward chat afterwards but I was able to find out Emilio was staying nearby for a few days and discreetly invited him to our hotel bar that night, telling him we would be there. We all left and she could not believe what she did. She asked me if I was OK with it and I assured her that watching her stroke his big cock was a giant turn on. We got back to the hotel around 4pm and fucked like no tomorrow. I blew multiple loads on her face and tits and she loved hearing me talking about Emilio's big cock as I uses her dildo on her.

That night around 9pm we headed down to the bar, fully refreshed. She had wanted to stay in bed and fuck all night but I insisted. And, as I expected, he was there. She did not notice right away but I guided her that direction and then she noticed. She put two and two together and gave me that grin again.

The next two hours flew by with drinks, flirting and recapping our beach escapades. I casually suggested we finish our drinks upstairs and nobody hesitated at all. We practically ran to the elevator and into our room.

Within two minutes she was grabbing his cock through his pants as I kissed her from behind and slid down her skirt to reveal a pink gstring. I started rubbing her through it from behind as she lowered his pants and boxers. They started making out as she was double fisting his rock hard cock and as I was finger banging her tight wet pussy. I motioned for him to sit on the bed which he did and she took the angle to suck him. She could not fit his cock all the way, only 8" or so and used a hand to stroke the base. I slapped her still gstring clad ass and continued fingering her. I could not bear it for very long and had to lower my pants and unveil my hard, thick cock.

Another few moments and I slid the soaking gstring aside and slid in my cock. She squealed with surprise as I was not gentle. I started pumping her balls deep as she continued to work his cock. My senses came back to me after a few minutes and I realized I did not want her to make him cum through oral. I pulled out and suggested she suck me for a while. Nobody complained and I took the place on the bed as she switched to deep throating my cock. Emilio stood next to her and she used a hand to stroke him at the same time. I took a moment when Ashley was eyes closed deep throating my cock to motion him behind her and he didn't hesitate. He positioned himself and slowly slid in.

Once again she squealed with surprise. Remember, he is not as thick as I am so the initial shock was not as much. He slowly slid deeper and stopped at which point she told him how big he is, thinking he was balls deep. He informed her he had more and then thrust all the way making her let out an absolute squeal of delight and surprise. She cursed many times as he pumped her a few times before she started to handle it. She got back to sucking my cock as he went to work. His strokes were so long I thought he had pulled out many times. A few minutes later she stopped sucking and came the hardest I have ever heard quickly followed by him erupting inside her, pushing him deeper still. They both collapsed on the bed satisfied.

I still needed to cum and I was very hard, leaking cum. I climbed on top of her, put my cock between her tits and titty fucked her as hard as I could. As I came close she opened her mouth, grabbed my cock and guided my giant load all over her face and mouth. I collapsed now.

A few minutes later Emilio stood up and he was hard again! Fucking my girlfriend was certainly doing the trick for him. He came over and sat next to her, she laughed, grabbed his cock and gave him a very mediocre handjob. As she gained more energy it got more and more vigorous. Then she did something I didn't expect, she swung her leg over him, positioned herself, grabbed his cock and slowly guided it into her still wet and engorged pussy.

I watched as she worked it down and down. Within five minutes she could go all the way up and down and she started to ride him like I know she can, her perfect ass bouncing up and down with her pussy massaging his entire giant Italian cock with every bounce. Her slapped her ass a few times and she rode him and moaned a she came all over him but he did not stop, he grabbed her waist and thrust his cock up into her over and over until he unloaded again, his cum dripping out of her pussy.

And once again they were both spent. Unfortunately by this time I was ready to go again. Rather than stick my cock in her cum filled pussy, I put a little lube on my cock, rubbed some on her and gave her a hard anal session, complete with me filling her ass with a big load. She stood up afterwards and she had cum leaking from both holes.

That ended the night, but certainly not the vacation. We had another night with Emilio and she gave handjobs to two other guys on the beach before heading home a changed couple.

Before long back in the States I had acquired friends with the intent of continuing what we had started in Europe. I brought Grant over one night to watch sports and hang out, although I knew that was not the real plan and he did too. And to be honest, Ashley probably knew it also. She had been getting fucked by a 10" white dildo named "Emilio" ever since we got back so it wasn't forgotten. We all hung out, ate, drank a little, talked and eventually got naked. I bet Grant on the final score of a game and the loser would have to run around house naked.

Well of course I knew that Grant was carrying a large stick and so when he lost and ran around the house it was hard to not imagine Emilio. He stayed naked as by the time he was done Ashley had her legs seductively spread, showing off a red silk undergarment. As he grew, her legs spread and he took the opportunity to walk over where she gladly grabbed his 9" white cock and started working her magic. He sat down on couch next to her and I quickly joined on the other side pantsless where she grabbed me with her other hand and double stroked us.

Grant began playing with her boobs and quickly got her topless as he sucked on them giving her huge hickies. I slid my hand to her thong and gave her a little rub action as she started to moan. One thing led to another and she was riding Grant backwards cowgirl as I stood in front and she sucked me dry. I came before either of them and took my place across the room to stroke my cock as they finished up. We all ended up cumming a few more times that night, each of us inside her as well as both of us masturbating onto her face to finish the night. Grant became a regular guest at the house, and on his 10th visit or so we took it up a level.

It started with her on top of him riding and me to the side getting a handjob. The thought crossed my mind that I really needed to pound her but didn't want to stop a good thing. So the next best option came to me, why don't I give her anal! I had seen it in porn and surely I could pull it off. I carefully positioned myself behind her without touching him, lubed us both liberally and slowly slid in. She kind of jerked initially as she realized what was happening. As I slid in she was very still until I got most of the way and then we all started a slow rhythm where she went down on his cock as I came out and then she came back up and my cock slid in deeper.