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My Best Buddy

My girlfriend helps my friend with his shyness.

I have a buddy, Chris, who’s been my best bud since we were kids. We grew up on farms, one canyon apart. Walking over the ridge between us to play famous explorer or some other kid’s game was pretty common when we were ten and nine and older. There was a big rock formation on my dad’s farm that likely had been put there by someone in the long past as a rock shelter that was perfect for two boys to use as a base when discovering the world. We always used to assume that it was probably Kit Carson or some other famous explorer who had built it.

Oh, by the way, my name’s Steven... Stevey to Chris.

Chris is a year younger than me, but he was the one who grew up to be an athlete. By the time I was a senior in high school and he was a junior, he was six-feet-five and the star on our better than average basketball team. I preferred baseball but wasn’t particularly good at that either. It was a good thing we had a small school or I’d have never made the team.

We were pretty good in school, typically getting A’s and B’s, but if Chris had one failing it would be that he was painfully shy with girls. I wasn’t exactly Don Juan, but at least I could speak to a girl without getting all flustered and making an idiot of myself (at least sometimes). I actually had a girlfriend in my senior year, Tina. She was my table-mate in study hall. We went to several dances together and even made out in the car a few times. Not Chris, though. We talked about it a few times and he simply couldn’t bring himself to ask one of the girls out or even start a conversation. Whenever a girl tried to start a conversation with him, he just got flustered and couldn’t put three words together in a logical string.

After I graduated from high school, Tina and I went to different colleges so our romance was pretty much over. Chris had one more year in high school, then he wanted to come to Oregon State with me. I enjoy mathematics and was very good at it. It was the one subject that I excelled above my classmates. That and physics were my straight A classes, even at the local Community College where I took classes more advanced than high school offered. Consequently, math was my college major.

I was looking forward to my friend coming as well. We’d been friends since we were old enough to know what a friend was and being hundreds of miles apart was difficult.

I met a girl at Oregon State. Our dormitory had a ‘big sister’ program where new freshmen boys were paired with one of the upper-class girl volunteers, typically a senior at another dorm, who took on the role of a big sister. My big sister’s name was Lois. She was nice and always helpful to me: showing me around the campus, encouraging me when I got homesick, and even introducing me to a couple girls from her dorm.

She arranged blind dates for me with two girls, Jocelyn and Sarah. Both dates turned out to be duds. It was probably my fault, but we just didn’t click. They were city girls and expected something different than a somewhat bashful country boy would provide. I know they were both bored the whole time.

Then, there was Elena. I recognized her as soon as Lois introduced us. She was in a couple of my math classes, Applied Differential Equations and The Theory of Numbers. She was the girl who I had been drooling over and never had the courage to speak to; straight, shiny hair, black as nighttime in a cave, to the middle of her back, a body a guy could only dream about and a smile that lit up the entire room. Plus, she was gorgeous. How a girl like her hadn’t had a steady boyfriend within the first week of school was beyond me.

Anyway, I was taking her on a date! That is if I could get past the blubbering idiot stage when Lois introduced us. I had reverted nearly to Chris’ level of shyness. Fortunately for me, she wasn’t the kind of girl you stayed shy around for very long. She was fun, fascinating, and most of all, even made me feel interesting.

Our first date was to a movie. I don’t remember the movie’s name or even what it was about, I was so enamored with the girl sitting next to me, intertwining her fingers with mine. We learned that besides mathematics, we had a lot in common: both of us were from small towns, although hers was in Western Oregon and mine in Eastern Oregon, we were majoring in mathematics, and we were Freshmen. Afterward, when I took her home, we sat in the car talking for probably an hour, getting to know each other. Then she leaned over and kissed me. It was completely different from the little bit Tina and I had kissed. It felt more like Elena was making love to my mouth when she kissed me. That night I felt like I had gone to heaven.

The next week in our two classes together, she moved to a desk beside mine, and we started studying together outside the classroom. She took the fun of mathematics to a whole new level. I guess I was a bit of a male chauvinist, thinking that mathematics was a guy’s specialty, but she proved me totally mistaken. She was always the first one raising her hand to answer any question and was clearly the star in both the classes we shared. I was only too happy to discover how wrong I had been.

On our second date, Elena encouraged my hand up under her blouse, and for the first time ever I felt a girl’s braless boobs. At the same time, she wrapped her hand around my boner over my slacks and squeezed. That night, after I went back to my own dorm, my hand was very busy under the covers relieving the pressure from my rock-hard cock. I was sure the girl was going to drive me totally insane.

We saw each other several times the following week, studying together. I had a hard time paying attention to what we were supposed to be doing when all I could think about was her bare tits in my hand. I didn’t even progress to the what-ifs beyond that.

That Friday night, Elena’s dorm held a Christmas dance in their ‘great hall’, and she invited me to be her date. I made it a point to buy a red shirt and green tie to wear with my only pair of black slacks. When I arrived at the dance, Elena was there to greet me, wearing a red dress that hugged her figure and looked fantastic on her. It had white fur around the hem, which was well above her knees, and the neckline, which showed off her beautiful cleavage; black fishnet stockings and green high heeled shoes. She was wearing perfume that smelled like feminine heaven. It was hard for me to grasp that this smart, gorgeous, sexy minx was actually my girlfriend.

Lois was there too, with her boyfriend, David. I had thanked her numerous times for introducing me to Elena and did so again that night. We got a glass of fruit punch (most of us were underage, so there was no alcohol) and sat at a table with Lois and Dave, listening to the music.

Elena was tracing little figures on the back of my hand with her fingers while we talked about school, home, and other things. When a song came on that Elena particularly liked, she leaned over and asked me to dance with her. It was a fast song so there wasn’t much touching, although she did bump her pelvis into mine just enough to keep my libido on edge. We danced several songs in a row and my brain was breaking free of the ability to think so that by the time we sat back down, all I could contemplate about was my girl. When she sat, it pulled her dress up her thigh, further eroding any possibility of rational thought.

A few minutes later, the DJ played a nice slow song and Elena pulled me out on the floor again. This time she wrapped her arms around my neck, snuggled her cheek against mine and pulled our bodies tight together. “Mmm, Stevey, I like this,” she whispered in my ear. No one had ever called me that name before, except Chris.

I liked it too, and that is perhaps the understatement of the month. She smelled and felt so good nuzzled up tight with me. We shuffled around the floor, cheek to cheek, and I know she had to have been feeling my boner through her thin dress. I knew that that night was going to be a massive masturbation session before I’d be able to get any rest.

This was how the rest of the evening went; fast dances, an occasional slow dance and visiting with Lois and Dave. I made several trips to the punch bowl to keep mine and Elena’s cups filled until the DJ announced that it was going to be the last song. That song was the first time during the night that we’d kissed. I felt Elena move her cheek away from mine, then her soft lips on mine and her tongue between my lips. Her hands were in my hair, scratching at the back of my head and pulling me tighter to her.

When the song ended, and it was time for me to go home, my cock was harder than I remember it ever having been. We walked back over to where we had been sitting, and people were already putting up the chairs. Lois and Dave were carrying chairs, and Elena and I grabbed some, too.

After the chairs were put back in the carriers and tables folded up, it was time for me to go home, back to my own dorm to masturbate with thoughts of a particular girl flooding my head. When I started to kiss Elena good night, she whispered in my ear, “Come upstairs with me?”

My heart started to beat a couple hundred beats a minute. I wasn’t sure she had said what I thought, until she went on, “My roommate is going with her boyfriend… and I’m on birth control… spend the night with me?”

Oh my God! Those were words I hadn’t even dreamed of ever hearing. She took my hand and led me upstairs, right in front of her dorm-mates. I might have been embarrassed about that but was still too shell-shocked… and horny.

Once we were inside her room, and my whole body was shaking with nervousness, fear, excitement, lust, and other emotions I didn’t even know existed, she turned around and started to unbutton her dress.

I’d describe the rest of that night, but this story isn’t about me, or even about me and Elena. It’s about my friend, Chris. Suffice it to say that it was the most pleasurable night of my life, by a factor of about a thousand, and that if I hadn’t been in love with my girlfriend before that night, I certainly was afterward.

The following week was finals week at the end of the fall term, then our three-week Christmas vacation started. I knew that by the time that school started again, I’d be out of my mind with missing her and wanting to repeat that fairy-tale, heavenly night.

We did see each other quite a bit during finals week, but only as study partners. I think she made an effort that week to be as unsexy as she could in order to keep our minds on studying, rather than what we both wanted. It didn’t work. Every time I saw her it was a supreme effort to think about anything other than holding her and making love with her.

Thankfully, we were both prepared for the tests even without the last-minute studying. I ended the semester with two A’s and four B’s. Elena’s grades were all A’s, most likely the top of every class.

At home during Christmas break, I told Chris all about Elena; well, maybe not ‘all’. He didn’t need to know about that night after the party. He was more than a little impressed when I showed him the pictures I had of her. I was still wishing that he’d get over his shyness at least a little bit and find a girl he liked. It certainly hadn’t happened yet.

My parents, too, were more than interested in Elena. I definitely didn’t tell them about that night. They were anxious to meet her and I was just as anxious to bring her home. I really wanted our relationship to be permanent as I admitted to myself that I was madly in love with her.

Our high school sponsors a Christmas basketball tournament every year, the weekend before Christmas Eve. Up to that point our team had been undefeated and Chris was the biggest part of the reason why. He was averaging twenty-six points and eleven rebounds a game. It was a four-team tournament and, as expected, we won both of our games to keep the championship trophy at home. Also as expected, Chris won the most valuable player award. I wished that I was half as good as him in sports.

It was a long three weeks at home away from Elena. We talked on the phone nearly every night, but it wasn’t the same as being with her at all. At least her sweet, sexy voice on the phone let me know that she hadn’t forgotten me.

I went back to Corvallis the day after New Year's Day. Winter term started the day after that. The evening after I got back to Corvallis, Elena was already there since she lives a couple hundred miles closer. The first thing I did, even before unpacking the car, was to pick her up. Our meeting was everything I’d hoped for. We kissed for what seemed like only a moment, but when I looked at my watch, realized we’d been making out for over an hour. There wasn’t anything I wanted to do more than go to bed and make love with her again, but unfortunately, we already had school the next day so agreed that we were off limits to each other until the weekend.

On weekends, we had three options: her dorm room, mine, or the car. We tried to make love at least one night every weekend, but given our housing limitations, it wasn’t always possible. Our first time after Christmas break was, if anything, even better than our first time. Maybe because neither of us were quite as scared or nervous, but it was incredible, fantastic, unbelievable, and any other adjectives I could think of.

By the end of March, when spring vacation started, I had fallen so madly in love with her that I didn’t even want to go home. Our families -- and Chris -- would have been devastated if we didn’t, though.

By then, Chris had gotten his acceptance letter from Oregon State. He had actually gotten a basketball scholarship offer from a small college, but his goal was to attend OSU and play for them. His team had come in third in the State, losing one game by a single point. He was determined to get a walk-on scholarship, or even play without one. He just wanted on the team and was convinced he could make it.

Chris and I had talked about his visiting the University at the end of April, and I told him he could stay in my dorm room, even if one of us had to sleep on the floor. Fortunately, Zachary, my roommate, said he could go home for the weekend so Chris could have his bed instead of the floor. I was anxious to show Chris around the college and especially for him to meet Elena. I hoped that maybe she could help him get over his shyness, at least a little bit.

I told Elena all about Chris, about our long-term friendship, how close we were, and how shy he was. When I suggested to her that, hopefully, she could help him with his shyness, she was agreeable that she’d try. Actually, she was eager to meet my friend.

Chris drove to Corvallis after school that Friday, about a five-hour trip. It was almost ten o’clock by the time he finally arrived. Zach had gone home earlier, and I changed his bedding so Chris would have a clean place to sleep. I made it a point to pick all the debris up off the floor, too.

We were both excited when Chris arrived. We sat on the beds in the room and talked until nearly one in the morning. He told me about the state tournament and nearly cried when he said he’d been the one to miss the last shot of the losing game, an easy jumper that he made nine times out of ten. “If we’d won that game, I’m sure we’d have won the championship game, too,” he said. The team that had beaten them by a single point won the championship game by more than twenty points.

I told him that we were going to pick up Elena first thing in the morning and she’d spend the day with us. When neither of us could stay awake any longer, we finally went to sleep.

We picked up Elena at nine in the morning. I thought Chris’ eyes might pop out of his head when he saw how much prettier she actually is than the pictures I’d shown him. She was wearing a silky, tan-colored blouse and a short, dark blue, leather skirt. I thought she had made it a point to look especially nice to meet my friend.

She greeted Chris with a big hug and kiss on his cheek. Chris climbed into the back seat of the car so she could sit up front, but she climbed in the back with him on the other side. On our way to McDonald’s for breakfast, she chatted with him, about college life and how she and I had met.

After breakfast, we parked the car and walked. Elena walked between us, hooking her arms in ours, keeping Chris close to her. We spent the day going from building to building, Elena making a point to include Chris in all her discussions. We showed him Strand Agricultural Hall since Chris intended to major in agriculture. Then Gill Coliseum where he wanted to play basketball, Memorial Union with the cafeteria, library and other student functions and several of the other buildings.

Chris seemed to be enjoying the day immensely, the same as Elena and I were. I was looking forward to my best friend being in college with me the next year. Between him and Elena being there, college would be about perfect.

We stopped at Pietro’s Pizza for dinner and got a family size sausage and pepperoni pizza. Elena had been working on Chris all day, trying to build up his confidence talking to her and kept it up during pizza. She got him to tell her about our childhood, how we’d walk over the hill to each other’s house. Of course, the hill grew about three times bigger than it actually was. She told us a little about herself, things she hadn’t even mentioned to me before, like how her dad took her out in his rowboat on the Willamette River and they’d spend the day together fishing and just rowing around. It was obvious how much she loved her dad.

We had talked a little about Chris’ basketball earlier in the day, but she asked him about the tournament and he repeated the story he’d told me about how they lost that one game by a single point, and he was blaming himself.

It was obvious that Chris was becoming more and more comfortable around Elena, letting his shyness fade, at least somewhat, into the background. Elena was trying to build up his confidence so, hopefully, he’d have a little more self-assurance around girls when he got back home. I couldn’t have been prouder of the girl I was going out with. I’d already decided that she was the girl I wanted to marry, and the way she was treating my friend only reiterated that.

We realized that we’d been in the pizza parlor for over two hours and walked back to my dorm. Elena came up with us and sat down on the bed between me and Chris. When Chris got up to go to the bathroom, Elena asked me how far I wanted her to go to help Chris and his shyness. He really seemed to like her, and to be honest, I was enjoying watching her flirting with him.

“I think… that I’d like you to do whatever you wanted with Chris,” I told her. I was wondering what it’d be like if Elena were to kiss him, how he’d react; how I’d react. Thinking about it was making me hard. It was obvious that Chris was sexually attracted to Elena, what red-blooded guy wouldn’t be? No matter what happened, I knew that I could trust Chris… and Elena.

When Chris came out of the bathroom, saying that he felt much better, Elena was sitting on Zach’s bed and patted the space next to her, asking Chris, “Sit with me?” Her leather skirt was already short, but when sitting on the bed, it had pulled up high on her thighs.

Chris sat next to her, noticing the expanse of her exposed leg. Elena asked him, pretending to not already know the answer, “Do you have a girlfriend, Chris?”

He laughed and told her, “No, I’ve never had a girlfriend.”

“Never been kissed, then?” she asked.

Chris looked down and shook his head no like he was embarrassed about it. I suppose he probably was.

She smiled at him and said, “We can fix that.” She placed  one hand alongside his cheek, pulled his face toward her and kissed him… on the lips… like a lover would. I saw her open her lips and work his lips open with her tongue.

She pulled his body to her and continued kissing him. I have experienced her kisses, like making love and had some idea how Chris must be feeling. Elena pulled away from him for a moment, looking straight at me. I didn’t know what she might be intending, but I nodded in the affirmative to whatever it would be. I didn’t think about it at the time, but I was putting my entire future in jeopardy, with the possibility of losing both my girlfriend and my best friend. All I could think of was that I wanted to see Chris and Elena making out.

She looked back to Chris and I heard her softly say to him, “I want you to make love with me.” Holy shit! This was going further than I had ever imagined. But I was a horny teenager and still wanted it to continue.

Chris’ eyes got wide and he looked over at me with a look of panic on his face. I think I was likely as shocked as he was, but by then I wanted it to happen, too. I wanted my best friend in the world to make love with the girl I knew I wanted to marry. If I’d thought for a minute that Chris was saving himself for someone special I’d have said no. But we had talked about sex before and he had simply been too afraid.

Elena turned his face back toward her and with her lips only about an inch from his, repeated, “Make love with me, Chris.” Then she closed the inch gap and her lips were on his once again. When Chris began kissing her back, I knew that my friend was going to go from an eighteen-year-old guy who’d never even been kissed to losing his virginity within a duration of a few minutes.

Still sitting on the bed, Elena pulled her lips from Chris and told him, “Unbutton my blouse.”

Chris’ fingers were shaking when he started fumbling with the top button of her blouse. Such a simple task, yet he could barely control his fingers, they were shaking so hard.

“It’s okay, Chris, you don’t have to be scared,” she told him and wrapped her own fingers around his to steady them. With hers guiding his, he managed to get the top button undone. Then she took hers away and let him continue. She’d helped steady his fingers so he didn’t have any trouble with the next button or the next. Her blouse gradually opened, revealing the thin, blue satin and lace bra, until the last button was undone and my girlfriend’s blouse hung completely open.

Elena took both Chris’ hands in hers and put them over her breasts. He began to massage and caress her over her bra. “Oh God, that feels good,” Elena moaned. She let him massage her a few moments, running her own hands over his chest, unbuttoning his shirt, then told him, “Take my blouse off.” He did, running his hands over her soft skin while he did.

When Elena’s blouse was off, she whispered to him, “My bra, unhook it.” Chris started to get up and move behind her, but she told him, “No, reach around.” Chris’ fingers weren’t shaking like they had earlier, and he reached around her and fumbled with the catch on her bra. It’s something he’d obviously never done before and wasn’t able to get it. I got up and with my own shaking fingers unhooked her bra and pushed the straps off her shoulders. While I had been doing that, Elena was pushing Chris’ shirt off of him.

“Suck them, please.” Elena’s eyes were closed. She was running her hands over Chris’ bare chest and whispering to him. I was transfixed, watching my best friend’s mouth wrap around my girl’s nipple and breast. Elena’s arms wrapped around Chris’ head and pulled him tight to her so that he had nearly her whole boob inside his mouth and the sucking noise co-mingled with Elena’s moans.

Her upper body was rocking back and forth with Chris sucking on her tit. I knew from experience with Elena that she’d gone from wanting to help Chris with his shyness to just wanting him. Sucking her nipples sends her libido soaring through the roof.

I was about to go completely out of my mind wanting to be where Chris was at that moment. I wasn’t sure how much more I’d be able to stand watching what I hoped was my future wife seducing my friend. It was so damned sexy. Every cell in my body was on fire. I couldn’t even begin to imagine how inflamed Chris had to be.

I couldn’t stop myself reaching behind her to unzip her short skirt. It had already ridden nearly all the way up her thigh, showing the tiny, blue panties she was wearing.

She pulled Chris to her other tit and was apparently at least aware enough that I’d unzipped her skirt because she lay back on the bed, pulling Chris with her, and lifted her hips off the bed enough that I could pull her skirt down and off, feeling the heat emanating from her soft skin all the way down.

That left Elena wearing nothing but those panties and Chris inhaling one of her sensitive tits all the way into his mouth. She was writhing and moaning underneath Chris’ body.. Elena pulled Chris’ lips back to hers and devoured him for a moment before pulling back half an inch or so and telling him, “Take the rest of your clothes off, too.”

Chris looked over at me one more time, “Should I be doing this?” he mouthed to me. When I nodded, he stood up and with his shaking hands undid his belt and pants, pushing them all to the floor.

Chris is a tall guy, like I’d mentioned before, six-feet-five. His legs and body weren’t the only parts of him that were long. We’d seen each other naked before on occasion but never with his cock hard and erect. He was at least eight inches.

Elena was lying on the bed breathing deeply, her face awash in desire, Chris standing naked next to the bed looking at her beautiful body. I don’t think he knew what to do next. “My panties, Chris, take them off,” she told him.

He leaned over and put his hands on the sides of her hips, grasping the lacy fabric with his fingers and pulling it down her legs. I wasn’t sure he’d be able to keep from coming when he pulled the satin down off her pussy lips. I know my seeing my friend seeing her was the hottest, most erotic thing ever.

As soon as she was fully naked, Elena pulled Chris down on top of her, his lips to hers and I heard very softly, “Make love with me, Chris.”

She reached down between them, taking his cock in her hand and guided it to between her pussy lips. She was obviously already wet as he slipped inside her all at once, the full length of him, and Elena’s face grimaced hard in her lust, letting out a low, continuous wail. If I’d thought I was having a hard time controlling myself before, the feelings had just intensified about ten-fold.

Nearly as soon as Chris had buried himself all the way inside her, he let out a loud groan and pushed himself hard into her with repeated short thrusts. His body shuddered, his face contorted and it was obvious he was already coming in my girl’s body. Elena’s hands had wrapped around his butt, and her hips lifted off the bed, pulling him in deep.

When his orgasm was over, after probably a minute of hard ejaculations, that had seemed like an hour to me, Chris collapsed down on her body, trying to catch his breath. Elena’s arms were wrapped around his back holding him tight. When he started to pull out, she said, “No, stay here, you feel so good.”

He started to apologize to my girlfriend for coming so quickly, but she kissed his apology away like the lovers they now were and told him, “Just wait a few minutes. We can do it again.” Then she led his lips once again to her breast where he suckled on her like a newborn baby, with his cock still buried in her pussy.

Elena held his head to her, starting to moan once again. I don’t know how long it was, maybe one minute or even thirty minutes, but he started moving his body inside her again and she reciprocated, pushing her hips up to meet him. His movements became more and more pronounced, until he was fully pulling out and thrusting into her, this time actually fucking her.

I watched, totally mesmerized. I don’t know why I didn’t feel jealous, but I didn’t… just so damned horny from watching Chris’ wet cock sliding in and out of her that it was nearly unbearable. Elena’s moans grew louder and her face twisted into knots more and more as she came closer to her own climax. When it finally did hit her, she’d wrapped her legs around Chris and was wailing, “Oh Chris, Chris, ohhh…” then she became totally unintelligible as her body went into spasms. Her painted fingernails dug gashes across Chris’ back, and he too orgasmed the second time of the night.

Both their bodies were covered in a sheen of sweat and I was breathing probably as hard as them. After a time, Elena rolled Chris over and extricated herself from his arms, walking across the room to my bed where I was intently watching her. “Strip,” was the only word she said to me.

I hurriedly peeled off  my clothes and Elena pushed me down onto my back, my rock-hard cock sticking straight up. She straddled me and sank onto me, enveloping my cock inside her soaked pussy. She ground down onto me and then pulled up so just the tip of my cock was still inside her and dropped again, grinding down once again. It was only three or four times until I felt the inevitable and my cum violently erupted inside her.

When my spurting finally subsided, she leaned over and whispered in my ear, “I love you.” That was the first time she’d said those words. I hugged her tightly to me and told her back, “I love you, too.”

We spent the rest of the night in each other’s arms.



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