An Awkward Route To Romance Pt 01

"You around? I'll come over," Bill, my very best friend, asked on the phone. He sounded excited.

"What's up?" I asked as he bounded into my bedroom.

"Bobby, you won't believe what I've been doing these past two days," he gushed, out of breath.

"Yeah?" I was used to Bill's exaggerated enthusiasm. Nothing new.

"Well, two days ago I was in my room, same as always, and wanted to ask Roger a question. I should have knocked but you know me. Anyway he was stretched out on the bed, naked. And you know what he was doing?"

"No, why don't you tell me?"

"He was rubbing his cock. It was big and stiff and he was running his hand up and down it. I watched from the doorway for at least a minute. Fortunately, his eyes were closed and he didn't see me. I gasped as a big wad of stuff shot out of the end of his cock and landed on his stomach. Three more spurts followed. I should have gotten out at that point but was stuck in place. I guess he heard me and opened his eyes. "Get the fuck out," he yelled.

"Damn, you caught him jerking off!"

"Yeah. Later he stormed into my bedroom and chewed me out for not knocking. I apologized all to hell and he gradually calmed down. Finally, I got my mouth in gear and asked him if it felt good. He looked at me in surprise.

"You've never done it?"

"No, but I know what you were doing."

"You need to get with it, little brother. You're eighteen and plenty old enough to beat off. Helps keep the frustrations in check. I was out with Susan tonight and expected to get some but we got to arguing over something stupid and I took her home. My hand is a poor substitute for pussy but much better than nothing."

"Does it feel good, Roger? Your face was all crunched up, like it was hurting."

"God, no. And yes, it always feels really good. So you've never done it? Want me to show you how?"

"I guess."

"He told me to take off my shorts as he got a bottle of lotion from his bedroom. He squirted some on my cock which was already half-hard. A tingle went through me when he grabbed it and started moving up and down. No one had ever touched it before, except me of course. It quickly became stiff as a board and just three or four minutes later I spurted. Four times, I think. God, it felt good. Just before it happened my cock got all tingly and the head became ultra-sensitive to his hand. I didn't know what to expect and suddenly I was squirting. Totally caught me by surprise.

"Anyway, that was the most exciting thing I had ever done. Yesterday we did more. He jerked me off again, same as the night before. And then I did him. It felt really strange to hold his cock. It was warm and hard and the head was so slick. He lasted much longer than I did, more experience I guess or maybe I'm not as good at doing it as he is."

I was taken by surprise by Bill's story. Sure, I knew what jerking off was all about but like him I hadn't done it. Sure, I have played with my cock and get it hard. But I didn't know enough to make it spurt. I suppose we are both a little backward when it comes to sexual things, maybe more than a little.

"So you think your brother has been doing it for a while?"

"Sure seemed like it. He didn't seem the least bit reluctant to do me or have me do him. Anyway, it felt really, really good. You interested?"

Sure I was but not sure if this was a gay sort of thing that I would regret later.

"I know what you're thinking, Bobby. Same thought at first went through my mind. I guarantee you, my brother isn't gay. He and his girlfriend fuck all the time. And he had a string of girlfriends throughout high school. Like he told me, what we did was just pressure relief. His girl wasn't available so he jerked off and then took pity on his naive brother.

"Yeah, he's always had a girl hanging around him."

"So, you want to try it? I'll show you what we did."

I pulled off my clothes and stretched out on my bed. This was already a turn-on; my cock was quickly stiffening.

"Nice cock, Bobby. You are bigger than me, plenty to hang onto."

He squirted lotion on it and started rubbing and within minutes I spewed cum all over my chest. Bill was right, the feeling was exquisite. After I cleaned up I did my friend. His cock was smaller but still plenty big. He forewarned me when he was about to orgasm and I covered his cock head with the palm of my hand, catching his cum. Less messy than when I spurted.

We had a new plaything and took advantage whenever we were able to get together, usually three or four times a week. Bill and his brother Roger also did it from time to time and asked me if I wanted to join them, something I was reluctant to do.

"Holy shit. You won't believe what we did last night," he burst into my room.

"What?"

"My brother sucked my cock and then I sucked him."

"You're shitting me."

"No shit. Roger came into my bedroom and asked how you and I were getting along. I had already told him we were jerking off each other. Then he asked if I wanted to try something else. Well, minutes later he had my cock in his mouth, giving me a blow job. I laid there watching as he bobbed his head over my cock.

"Just like when we jerked off each other I started to get that funny feeling and knew I was close. I warned him but he kept going. The next moment I dumped my load into his mouth and he swallowed it all! God, I couldn't believe he did that. I have to tell you, hand jobs are fun but blowjobs are better, much better."

"So then what did you do?"

"Nothing. Roger got up and went to his bedroom. I lay there in a daze. The next day everything was normal, nothing was said by either of us. Now I'm wondering what will happen tonight. Will he want to do it again? Fine with me."

"So how did it go last night?" I asked the next morning, hardly able to contain myself.

"He sucked me again. I was more relaxed this time so enjoyed it even more."

"Do you think he's going to expect you to reciprocate? You know, give him a blowjob?"

"I was wondering the same thing and trying to decide if I would do it. I mean, I've jerked him off plenty of times but I don't like the thought of having him squirt into my mouth."

"Maybe you could have him warn you and you take it out at the last minute?"

"Yeah, maybe. And maybe he won't ask."

I didn't see Bill for a couple of days but did get a text from him. "I did it." Now to await the details.

"So, I'm all ears. Tell me what happened."

"Well, I expected him to suck me like the other times. Instead he stretched out on the bed, nude, and placed my hand on his cock. "Bill, I want you to suck my cock. Will you do it for me?" he asked.

"I fondled his cock for a minute, trying to make up my mind, knowing full well I would eventually do it. And I did, trying to mimic how he had sucked me. I started licking the head like an ice cream cone, then the sides, and then taking it into my mouth. I was only able to take about three inches, not nearly as much as he took me. When I started to gag he told me not to try too hard this first time.

"Anyway he did warn me when he was ready to cum but I was a bit late in getting it out of my mouth. I actually swallowed some and the rest landed on my face. He said I did a great job. I'll do you if you like."

"Suck my cock? I'm not gay and I didn't think you or your brother were either. Besides, who wants to taste cum?"

"It wasn't too bad but I didn't get most of it. Trust me, Bobby, when he sucked me it felt so good. I'll admit I wasn't wild about doing him but in a way it was kind of neat, playing with it, licking. I tried to do the same as he did to me. We are going to do it again, soon, and I want to try to take more of his cock. I'll do you even if you don't want to suck me."

Minutes later my cock was in his mouth. He licked around the head and swirled his tongue around the crown. Then he licked up and down the shaft from the head to the base while he fondled my balls. My cock was now back in his mouth, taking me half-way. As he bobbed up and down, more and more of my cock disappeared into his tight throat. He gagged but after several attempts was able to take me deeper. Just a couple of minutes later I grabbed his head and pumped a huge load of cum directly into his throat. Three more spurts followed. Having never had a blowjob I couldn't believe how good it felt.

I felt obligated to reciprocate but couldn't bring myself to put his cock into my mouth.

As he was headed home he turned, "I almost forgot, Roger is inviting you and me to his apartment for some BBQ this Saturday. Wait until you met his girl, cute and great body. And she's really nice, you'll like her."

I did more than just like her. I fell in love. She fit my eighteen-year-old image of the perfect girlfriend, slender, blond, killer body. She wore a snug top that showed plenty of tummy. Her shorts were snug and accentuated a great bubble butt. Her camel-toe was clearly visible. No panties? She held my eyes for a long moment and I blushed madly. I got caught!

****

We were invited to watch the game the next Sunday at her apartment with Roger supplying the beer. I was very anxious to see his girlfriend again. Bill's brother said she had a really bad reputation in school and was suspended for having sex in the locker room with a bunch of guys.

"Really? What happened?"

"Some guys involved said she sucked their cocks. The real story apparently was that she did much more than that, actually fucked half the team. It was a big deal at the time but Roger just heard about it since she went to a different high school."

"Sounds like a real slut. Funny, she didn't come across to me that way. But she did have those "fuck me" shorts on, made my eyes nearly pop out of my head. Those shorts looked painted on and were so low it barely covered up her pussy. I wonder if she had panties on."

"She didn't, I asked my brother. Poor Roger must have a constant erection, I sure would."

"Yeah, poor Roger. How long have they been dating?"

"Both were freshman and met last November, shortly after school started. My brother said they had a number of dates before they did anything. She claimed to be a virgin, which Roger now knows was bullshit."

"Did you ask him what's so interesting about this game on Sunday?"

"Yeah, he told me but I'm not supposed to say."

"Come on, Bill, cut that shit. Tell me."

"He wanted it to be a surprise but I was persistent. Roger says he's got it arranged with Susan, she's going to fuck us both!"

"Don't shit me. You believed that bullshit? So his girlfriend is going to fuck us just because he told her to?"

"Hard to believe, isn't it? I've been around her a number of times and she never came on to me. Always seemed quite proper. Anyway that's why we are supposed to go over there on Sunday. Roger wants me to have my first pussy. And you owe me, Bobby, big time since you are also invited. Personally I can't wait."

"I still can't take this seriously, but, damn she's one great piece of ass. I would do her in a minute."

"Yeah, me too. Roger said it's past time for me to get laid. He wanted my first time to be with someone who knows what to do. She apparently meets that criteria. And he said she has the hots for you so I guess that's why you are invited too. I saw how she looked at you and you saw it too."

"Yeah, embarrassed the hell out of me. Sure going to be a slow week until Sunday."

****

Susan sat on the sofa and motioned Bill and me to sit beside her. I looked at Roger and he nodded his ok. Two beers later and she had a hand on both of our crotches. I needed to take a piss but had a big bulge in my jeans. I guess I shouldn't have worried too much as Bill had one too.

When I returned I was amazed to see her unzipping Bill's jeans. She reached in and pulled out his cock, which immediately stiffened. "Come over here Bobby," she directed, pulling down my zipper. "Oh, nice one! You are a lucky guy and going to be really popular with the girls. Assuming you like girls," she added. "Roger tells me you guys have fun together and Bill sucks cock."

Bill and I looked at each other, embarrassed that she knew.

"That's ok. I know how it must be when you're not getting any pussy. Roger says he got you started and who better to demonstrate?" she added, giving him a smirk. "How about you guys show me?"

Oh, god, how embarrassing. Even Roger hasn't seen us do it.

"Time for a demonstration, guys," Roger told us. "Come on, stand up and take your clothes off. Do it."

Bill and I looked at each other, totally red-faced, our cocks sticking out of our jeans. He pulled off his pants so I followed suit. Moments later we were standing in front of Roger's girlfriend, cocks and ass on display.

"Come on guys, we haven't got all day," Roger directed. He was enjoying our discomfort. "Bill, suck him and maybe Susan will let you fuck her. Right Susan?"

After Bill sucked me, I stroked his cock until he came all over my hand.

"Go sit on the sofa, guys. I'm going to show you how to fuck. Get ready, Susan."

She stood up and undressed. Perky tits, a shaved pussy, and bubble butt, a teenager's wet dream of a girl. She turned to me with a sudden megawatt smile. "You like?" I was struck dumb and could only nod my head. She laid down on her tummy and spread her legs, exposing her pussy. Roger, now also nude, straddled her. Taking his stiff cock in hand, he slid it up and down between her legs.

He found her pussy and pushed. It was so sudden that she gasped with the abrupt penetration. Not wasting time, he thrust deep into his girlfriend, gradually going faster and faster. Bill and I were laser-focused on the junction of her pussy and his cock. This was tons more exciting than watching any porn.

His balls slapped up against her crotch on each thrust and her pussy made a sucking sound. He fucked her hard and only three or four minutes later was pumping cum. Her pussy was puffy and gaping open. Susan remained on her tummy, legs still spread.

"Push it out, Susan. Show the guys my cum. Neat, huh? Bill, get over here and fuck your first pussy. Susan likes lots of cock, don't you honey? The more the better."

Bill moved the head of his cock around until he found the right spot. Emulating his brother, he quickly thrust into her pussy causing her to grimace. Two or three minutes of hard, fast fucking and he was done. Her pussy lips were swollen and more cum leaked from her stretched vagina.

My rock-hard cock was ready, more than ready. I reminded myself from watching porn that girls like it slow. I rubbed my cock up and down between her lips, coating the head with the liquid and cum leaking out. Then I pushed in, but just a bit, maybe an inch. I wanted so badly to shove deep but forced myself to hold back. Each time I pushed my cock went a little deeper. Her pussy was so hot and slippery from two loads of cum; the snug feeling was exquisite.

"Damn, you're big, Bobby. Go slow, please." It was her first words since Roger started fucking her. I was now fully inside and held my position for a moment, then slowly withdrew until just the head was inside. In and out, I was trying to emulate porn fucks. Fucking pussy wasn't anything like having my cock sucked. Her pussy tightly gripped the entire length of my cock. I was enveloped in slippery warmth.

"Now go faster, Bobby." Just what I wanted to do. She made little noises, little murmurings and I felt her pussy tighten down on my cock. I exploded, three or four spurts of cum deep into her already overflowing pussy. I didn't last much longer than Bill but it was a great three minutes.

Susan got up and went to the bathroom. Later Roger cooked some hot dogs on the grill and we watched the game. I felt very awkward having fucked his girlfriend and now making small talk about some stupid game. Finally, it ended and Bill and I got ready to go.

"Well, guys, how did you like your first taste of pussy? Susan is a great piece of ass and loves to fuck. Let's do this again next weekend, ok? Give you some more practice." I looked at her, embarrassed for Roger's graphic and brutal description of his girlfriend. She turned and walked back to the kitchen.

Bill and I partied with Susan and his brother one more time. She sucked our cocks and then taught us how to eat pussy, then Roger fucked her. Our cocks got hard again watching them. I wasn't nearly as nervous this time and really liked fucking her. I still didn't last very long, nor did Bill. As we were leaving Susan gave us big hugs and I got a big kiss. She pushed her tongue into me even though I probably still tasted like pussy. Roger noticed and didn't seem happy.

And then school started. Bill and I were freshman and roommates. He said Susan broke up with his brother, which really didn't surprise me. I mean, what guy wants to share his girlfriend? Something wrong there.

Bill borrowed a bunch of porn DVD's and we were all set to continue playing with each other's cock. On the other hand, there was some mighty fine pussy walking around the campus. Too bad we were way too shy to try to snag some. Give it a little time, I told myself. If I did get something going at least now I had some sexual experience.

"Oh, there you are. I've been looking all over for you," Susan exclaimed.

I looked up with surprise, not having seen her since that second time together. She kissed me on the cheek, giving me time to collect myself. She sat down at my table in the school cafeteria and continued the charade.

"You must have been hungry, I thought you would wait for me. I'll go get something," she said, not giving me a chance to reply. Damn, she looked good. Much more conservative dress than before. Of course almost anything would have been more conservative. She looked really classy and it didn't tone down her sex appeal a bit. As I waited for her to return, I wondered what in the hell? Several of my classmates were staring at me. Good ol' Susan, she just enhanced my stud rating by 100 percent.

"Can you come a bit later, I want to get some things from the grocery store? We're eating home-cooked tonight," she added as she sat down next to me.

"Sure, what time?" I finally got my brain and mouth in gear. Play along, you idiot.

"How about seven? That gives us plenty of time to eat and relax." I noticed the guys nearby hanging on every word.

"God, who was that girl?" one of them asked after she left.

"Susan, my girlfriend," I greatly exaggerated but what the hell. He stared at me in disbelief. "We started dating during the summer," I further embellished. "She's a really nice girl, a sophomore. What she sees in me, I don't know, unless it's my great personality and sexy body," I laid it on thick with a big smile.

"Whatever it is, she sure seems attached to you. She's one classy woman. Does she have any friends that look like her?"

****

"Great place."

"You like?" as she showed me around her new apartment. "All to myself this year."

"How can you afford it? Must be a thousand a month."

"Twelve hundred. Mom and dad decided I needed to upgrade from the shared dorm I had last year. I didn't turn down their money."

"Well, it's very nice. Ok, back to my question, what was lunch all about?"

"I just couldn't help myself, Bobby," she answered with a laugh. "I had been hoping to see you all week. Did you like my little show for your friends?"

"Everyone noticed! And I sure liked it. I heard you and Roger broke up."

"Yeah, just before school started. You remember when we first met at Roger's BBQ? He said I was eating you up with my eyes. He got pissed but I couldn't help myself. There was some sort of instant mutual attraction. I saw it in your eyes too, not to mention your heavy blush.

"That first time when we had sex was a really awkward situation. You must have thought me a terrible person, fucking two guys I barely knew. That really wasn't me but, anyway, it happened. You and Bill were so nervous but I gave you good marks for effort. Maybe you didn't know but I had an orgasm while you were fucking me.