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The Girlfriend’s Friend I still remember the first time I saw Jess. I was waiting for Caitlin in the food court. Caitlin, my latest crush, was there to meet me for my lunch break. Since we had just started dating everything was exciting and she loved showing me off to her friends. Little did I know, Jess would end up causing me years of frustration and eventually show the world that I was nothing but a loser. Fast forward five years. Caitlin and Jess are now roommates at the University of Florida. They live in a nice little student apartment complex just off campus. Caitlin and I are very content with a really active sex life. I don’t go to the same college but since I live just over an hour away we see each other often. I’m going to a small community college with plans to attend med school eventually. Life is great! My Caitlin is a striking girl. Long brunette hair, green eyes, and a pretty decent figure. She’s got a very pretty, innocent look. In fact, she was innocent. I was the first guy Caitlin had ever had sex with. She wouldn’t really talk about it but I’m pretty sure she had never even seen a cock until we got together. The first time we hooked up she was 19 and I was 22. She let me fuck with no condom and I pulled out and shot cum all over her little tummy. From that point on every time we had sex I would cum all over her belly or her tits and she really seemed to like it. Jess couldn’t have been more different than Caitlin in the looks department. Caitlin was tall and pretty. Jess was short, about 5’2", and fiery. She was a pale little strawberry blonde that weighed about 90 lbs soaking wet. Despite her small stature she had a very unique disposition. She always got what she wanted. When Caitlin and I first started dating Jess kind of became my friend too. We got really comfortable around each other and hung out all the time. Jess dated lots of different guys, but I never liked any of them. Most of the time they were douchebags that just wanted to fuck. Every now and then Caitlin and I could hear guys pounding Jess through the apartment walls. I always thought it was kind of hot listening to her get fucked, but Caitlin would always get super pissed and go right to sleep. One time in particular Caitlin was giving me a great handjob and quit just because we could hear Jess moaning. I had to go the bathroom and jerk off just to go to sleep that night. "Hey babe." Caitlin said as I walked into the living room the night everything changed. "Hi!" I exclaimed. "Let’s get drunk!" It was Halloween night and we were going to a huge party. Caitlin was dressed as an Indian and I was a cowboy. Jess was wearing a slutty Girl Scout outfit. At the time Jess wasn’t dating one guy in particular, but had a thing going on with a few dudes. One guy seemed to come around a lot. His name was Chad. He was a typical frat guy with a cocky attitude. His family was loaded and he didn’t give a fuck about anyone. I hated when he would come over because he would basically pretend I didn’t exist and the girls loved to flirt with him. I remember being super stoked to have the ladies with me as we were leaving. That is, until Chad pulled up in his Acura. The first thing he said was "I can’t believe you guys dressed up for this shit." That was it. Jess and Caitlin decided we should ride with Chad so we left for the party. So my biggest problem with Caitlin is that she wouldn’t give me head. I had dated lots of girls before her and almost every single one sucked my dick. Her mom had kind of drilled it into her head that nice girls don’t blow guys. While that may be true, blowjobs were always my favorite thing sexually. Nothing felt better than cumming down a girl’s throat and feeling her swallow my load. Jess, on the other hand, talked all the time about blowing guys. I remember a story that was going around about how she sucked a guy off in the middle of a crowded party. Supposedly she just sat on the couch and sucked his cock with people all around. Something about hearing that story made me so hard! I could kind of imaging Caitlin blowing some dude in the middle of the room. I guess I should describe myself. I’m your average 175 lb, six foot guy. Blond hair, blue eyes, in pretty good shape. My cock is actually kind of big; like almost 7 inches and pretty thick. For some reason though I always felt like I was kind of a loser. Like every guy seemed to be better than me somehow. It was just a feeling I had, I never said anything because I didn’t want my girl to feel like I was a pussy or something. Jess knew though. She had to have because she had a plan to make me look like a giant bitch. "I can’t believe you don’t suck dick!" Jess was saying to Caitlin as I came back with their drinks. "Well I can’t believe you suck as many dicks as you do, slut!" Caitlin laughed. "Maybe I should teach you how to blow a guy on Mike!" Jess teased. Oh yeah, my name is Mike by the way. I couldn’t even react I was so embarrassed. I didn’t even look them in the eye. "You’d probably love that you nasty hoe." Caitlin joked. "But seriously, I think you’re making Mike blush! Let’s talk about something else." The thing is, she didn’t seem to mean that. She was saying it for my benefit obviously, but there was something kind of there that she wasn’t saying. After that the night went along just fine, lots of dancing and drinking. It was a fun night! Then we got home. I was just coming out of my drunken stupor. I guess it was around 2 AM. I could hear some sounds in the living room, but I wasn’t sure who was talking. There were a few voices, at least one guy. "See Caitlin, it’s not that hard." Jess was saying. "I know, but I’ve never done it and that thing looks fucking huge! I can’t fit it in my mouth! Plus what do I do if it shoots before I get it out?" Caitlin asked. "You swallow it you fucking slut!" laughed the guy. The guy. It was fucking Chad. "I’ll tell you what. Jess can show you for a few minutes. You take off your clothes and get ready. Before long you’ll be dying to take this big dick wherever I want to put it." Caitlin laughed. "Shut up, I’m only doing this so I can learn to suck Mike off. He deserves a good blowjob." "Girl, Mike is a fucking fag." Jess mocked. "He fucking passed out after three shots. Chad had half a bottle of Crown and pretty shaved pussy is going strong. I guess you can see that though." By now it was pretty clear what was going on. I peaked around the corner like a scared little bitch. There was Jess, kneeling in front of Chad. She had tiny little yellow panties on and her shirt was pulled up so he could see her tits. My girlfriend was sitting on the couch fully clothed, but obviously she wouldn’t stay that way for long. She had actually started sliding her little Indian skirt off, lifting her butt up off the couch so she could shimmy it all the way down. Her feather headband was laying on the coffee table. "So the key is to get your hands involved and change your speed every now and then." Jess was instructing Caitlin. "Watch how I do it." Jess started sucking the tip of Chad’s cock. Slowly at first, but then she started speeding up and going down further and further. I could just see the side of Caitlin’s face. She was staring with the widest eyes! The sight of her best friend sucking a dick was definitely interesting to her. By now she was down to her pink thongs and black bra. "Hey, you should play with your pussy." Commanded Chad. "I like seeing those little pink lips while another bitch sucks my cock." Caitlin immediately starting rubbing her little pussy through her thongs. "No, move them over. I want to see your cunt." Said Chad. My girlfriend listened to him. By now Jess was totally into sucking that dick. She was actually getting to his balls. For the first time I had a clear look at his cock. Remember when I said I always felt like every guy had something a little better than me? Well, Chad had a lot better than me. My cock is decent, but nothing like his fucking monster. His dick had to have been 9 inches and was so thick that Jess couldn’t really fit her hand around it. Caitlin was mesmerized by his cock, I could tell. "I guess maybe I could try for a minute." Said Caitlin timidly. "You bitch!" screamed Jess laughingly. "I knew you were ready to be a big dick slut!" "Hahaha!" laughed Caitlin. "I’m not a big dick slut, I just think I can do what you’re doing. It doesn’t look that hard…" Caitlin slid to her knees in front of Chad. He was kind of pushing her down in front of him. I never treated Caitlin roughly, but she was responding like it was something she enjoyed. When she finally got in front of his massive dick she sort of reached slowly and wrapped her hand around it. She was clearly not used to that thick of a cock, but seemed to be adapting pretty well. She gave it the smallest kiss. She had never kissed my cock. "Fuck yeah, slut! You’re my cock sucker now!" teased Chad. "I’m not!" laughed Caitlin. "I just want to try. Besides, Jess is gonna finish you off. I’m just going to do it for a second." Well. That second turned into a minutes, and that minute turned into five minutes. My cock was raging. I could see my beautiful girl’s brunette hair bouncing up and down while she took that asshole’s cock in her mouth. She even went to his fucking balls a few times like Jess had shown her. All along Jess kind of sat beside her and rubbed Chad’s legs and balls whenever Caitlin wasn’t on them. He was clearly enjoying teaching my girl how to suck a dick. "Ok girls, I’m gonna cum in a few minutes. Where do you want it?" asked Chad. Nobody answered but the girls looked at each other. "I say Caitlin gets it." Said Jess. "No way!" laughed Caitlin. She was still pumping his cock with her hand. "I’m not gonna let your man nut down my throat. Especially since my man is sleeping right beside us!" "It’s decided then." Said Chad. He kind of grabbed Caitlin’s head and started pumping her mouth. She resisted a little, but then just let him. She started rubbing his balls. Jess was giggling and loved every second of it. "Uuuggghhhh, fuck yesssssss!" moaned Chad. His balls were pumping and he was cumming down Caitlin’s throat! Seeing my little girlfriend take a cumshot like that almost caused me to nut right in my pants. "Tell me you didn’t like that?" laughed Chad. Caitlin just laughed and swallowed his cum. She was giggling like a little girl and cum ran down her chin onto her bra. "Well Chad" mocked Jess "I told you I could get her to suck your dick. Wait until tomorrow night, we’ll get her boyfriend to hold your cock while you shove it in her little pussy." Caitlin just sat there smiling. writedatdirt