Boy Story: The Road Taken - 43. The Jenny Situation

The Jenny Situation

I suddenly heard a phone ringing, and Parker picked it up. We were still in bed on the morning (late morning to be exact) after Pride. Parker had a portable phone dock on the night table next to the bed. As usual, we were naked under the covers.

“Hello!” Parker answered after clearing his throat. And then I listened to one side of the phone conversation.

“Jenny! Wow! It seems like forever…Yeah, the trip was great…Yup, he’s good too…He’s right next to me…You wanna say ‘hi’?”

He put the phone up to my ear. ”Hi, Jenny!” I blurted out. “Hi, Matt!” I heard on the other end. Then Parker took the phone back.

“Yeah, yeah, it’s been really busy. We went to Pride yesterday…No, we were in the parade. It’s a long story…What’s that?...Oh?...yeah…uh huh…noooooooo!…Oh my god!...Oh my god!...who with?...David?...David who?...uh huh? The one with the really nice bum?...nooooooo!… Oh my god! Isn’t he a Junior? Yeah, yeah, a Senior in September, right…Uh huh……Did you know him before?...Oh my god!...Haber, isn’t that a Jewish last name?…

Parker began playing with my nipples and they quickly became two very hard BBs.

“Uh huh…But I thought...really…wow!…Did he use a condom?... Ha ha. Yep, in the wallet like every high school guy…Oh my god!…nooooo…he did? And?...…he did?...it was?…Oh my god. I can’t believe it…Is he big?…Uh huh…oh well, you can’t have everything…that’s about average, ha ha ha ha…”

Parker began sucking on my nipples interspersed with his conversation.

“I can’t believe you!...You’re like Mrs. Robinson…Don’t you know the movie?…The Graduate…older woman seduces younger guy…I know, just kidding, it’s only a year difference…yeah, that’s nothing…Uh huh…We should go out on a double date sometime…Matt, can drive…movies? Eh…what about a drive in?...There’s still one left out in Mendon…I’ll ask him…Oh my god, I just can’t believe it!..."

"Whoa, we have a situation here (he said looking under the covers) gotta go. OK, I’ll call you later! OK, bye.”

The nipple sucking had produced the usual effect on me. He turned off the phone and tossed it on the empty side of the bed. I looked down and he was visibly growing as well. He tore the covers aside and began to use his mouth on me. I felt like saying, “What the hell was that conversation about!” But then again, I was getting an incredible blow job, so the phone conversation story could wait.

“Oh fuck! That’s sooo good!” I said as I could hear my hard, wet cock forcing itself down his throat.

I couldn’t keep from moaning. It was involuntary at this point. After about 15 minutes, it was time. I managed to utter “Oh fuck, fuck!” and my fluid spewed forth in waves as he pulled back so most of it would end up in his mouth. I could feel the suction increase as he drained my well. He devoured it all and hummed his appreciation, “Mmmmmm.” It sure helps when the person giving the blow job really enjoys what he's doing. It’s even better to get a blow job when you’re not even expecting one.

As we lay there for a few seconds catching our collective breaths, I was guessing it was now time to return the favor. But before I could, Parker grabbed me and pushed me down onto my stomach. He immediately went face first into my ass crack and began eating me out. He continued his commentary, “Mmmmm mmmmm mmmmm.” And he went deeper and deeper with his tongue. Then he rose up, slapped each of my ass cheeks, grabbed the lube, greased up my hole and his wood, and entered me all at once. He felt so big in me. As my fists clutched the bedding, I imagined his cock coming up my throat and out my mouth. That’s what it felt like anyway…extreme penetration into the depths of my core.

“I think you’re ready to take it to the next level,” he commented.

“Take what to the next level?” I groaned.

“Your talents as a bottom,” he informed me.

“But I’m a top!”

“Not today!”

His cock was in me, but he wasn’t humping me yet. “Now, I want you to try to shit my cock out your ass,” he instructed.

“But how?”

“Have you ever taken a shit before?”

“Of course.”

“Then you are familiar with the process. I want you to imagine my cock is a turd up your ass, and I’ll leave it right where it is. And I want you to try to shit it out,” Parker instructed.

This was odd because whenever he had fucked me in the past, I always resisted the urge to push. I always clenched my butt hole and fought hard to keep it in me. Now he was telling me to do the exact opposite. Push it out? Instinctively, it seemed like the wrong thing to do, but I trusted him and followed his direction.

I waited until I felt the urge to crap and I began to push. I imagined my hole would simply push his cock out. As we all know, the shitting process relies on light muscle movement and some gravity. The muscle movement is dilation of the rectum and anus, basically opening up the back door.

“Now push like you’re going to fart,” he commanded. My muscles felt like they were properly positioned to give it a try.

I pushed but his cock didn’t move because Parker maintained opposing pressure to keep it from coming out.

“Oh yeah, now you're opened up. I can feel it,” he said.

“Yeah, but it’s not coming out because you’re pushing against it,” I responded.

“That’s exactly what we want. Now just try to maintain that open feeling while I fuck you.”

He started to pump back and forth inside me. I maintained focus on keeping my muscles dilated and therefore myself open. It was an amazing revelation. I was wide open with his cock sliding in and out of me without restriction. The usual discomfort was decreased by about half and I was able to enjoy more the feeling of being penetrated accompanied by a couple of stinging slaps on my ass cheeks.

With this new trick, I was able to take it like never before. He began pounding me like he meant it. I grabbed a pillow and began moaning into it. I certainly didn’t want his mother to hear. You know those movies where a woman is getting screwed and fakes a loud orgasm? That was me that day. But I was not faking it! He boned me long and deep, and after about ten minutes, my cock unexpectedly shot again into the bedding.

“Parker, I just came again…on your comforter!”

“OK, hold that thought!” Then he wrapped his arms around my torso, grunted several times, let out a long breath, and said, “There. Now I'm done, too!”

He got off of me and rolled me onto my back. The spot where I had been was now visible. “Wow, you’re right. You came on my comforter!”

“Of course. Why do you think they call it a CUM-forter,” I joked.

“Ha ha. I didn’t know you were multi orgasmic…and so much volume for a second shot,” he stated. “I might have to take you out in the yard from now on every morning to milk you!”

“Ha, I’d love that…and so would the neighbors, I’m sure,” I replied.

“I wouldn’t be doing it for you or them. That would be purely for my enjoyment,” he admitted.

“Gee, I’ll have to start bottling it,” I joked.

“Then I’d be your best customer,” he claimed.

“Ah, I’d give you yours for free!”

“Yeah, but I get it for free already. Maybe I should rethink this.”

“Hey, did you just come in my ass?” I asked.

“Um, maybe,” he said with a devilish grin. “Why do you ask? Did you splooge on my comforter in retaliation?”

“No, I think I feel your little swimmers trying to fertilize my prostate!”

“Ha, ha. Well, then your prostate must be way up in your intestines!”

I did feel a slight tingly sensation on the reverse of my prostate. It must have been from the sudden overstimulation.

I pulled him on top of me and we kissed. “I’ve never come twice in one session before. You fucked me so good,” I admitted.

“Pretty good for a bottom, huh?”

“Pretty good for anyone,” I added.

“Would you say it’s the best you’ve ever had?” he asked.

“You’re the only butt sex I’ve ever had.”

“That’s not true. You have been fucked by someone else.”

“Oh yeah...I almost forgot. What’s his name?”

“Nathan.”

“Oh right. Nathan. Yeah, he was pretty good, too. But you’re better.”

“Would you say I'm the best?”

“No, if it’s between two people, it’s the better of the two. If it’s three or more, then you can say the best.”

“You mean, I have to find one more guy to fuck you, so that I can be the best?”

“I’m afraid so, that’s how the English language works.”

“Wow, I never imagined the English language and butt fucking were so closely intertwined.”

“Ha, ha. Well, bottom boy, how many has it been for you?” I queried.

“You know, I’ve never counted before. Let’s see—excluding multiples—one, two, three, four…hmm…hmm…seven, including you!”

“Wow, you’re only 18 and you’ve been butt fucked by seven different guys?”

“Well, not fucked but had sex. Why? Is that a lot?” he asked.

“I don’t know. It would be a lot for a straight boy. But with gay guys, maybe it’s not that many.”

“Well, I was a big slut at age 16. I was suddenly legal and I made up for lost time. I always traveled with condoms and lube packets," he explained.

“Really, right out of the gate?"

“I got tired of just masturbating all the time. I wanted real sex. I even got fucked by a teacher once."

“You were fucked by one of your teachers?"

“No, not one of my teachers...just a teacher. I told him I was 17, so he wouldn't feel like a total perv. He was really hot. I was at one of my high school football games. We were the away team, but it was the town next door. I did a road trip with a couple of friends, one was Jenny. I ran into this hot guy over near the snack bar. He invited me to go home with him, so I told Jenny I was bored and I was going home with a different friend.”

"Just like that?” I asked.

"I told him I thought he was hot," Parker surmised. "I think that helped set things in motion.”

"And you didn't become his lover?” I asked.

"Nope. He was 31 and he did have a big dick...not like yours...but ample size. He was really good in bed, but after we had sex, I discovered he was married.”

"Uh oh. How did you figure it out?”

"Well, the ring, the wedding pictures, and the female products in the bathroom were dead giveaways.”

"Ouch! And that was it, like an anonymous hookup?”

"It wasn't anonymous. His name was Paul and he said he was a Science teacher at the neighboring high school. Teacher or not, the sex with him was really hot. But when we were done, he didn't want to give me his number because he was married, and I didn't want to give him my number because he was married. Anything beyond that one time would not have ended well.”

"Wow!”

"You know the funny thing...I went to Target about a month later with my mother because I needed dress shoes. So we're up at the register checking out, I look up and there's Paul staring at me from another checkout line. Our eyes locked and he's with his wife. We both froze for a couple of seconds. Awkward! So I just gave him a discrete head nod of recognition, and he returned one back. His wife was gabbing away oblivious and I know he'd just love to drag me out back and fuck my brains out. Of course, I would have loved that too. But I was with my mother and he was with his wife, so..."

"I guess he was the one that got away”, I summed up.

"He was the one that got away as soon as he got married.”

“Oh wait…while we’re on the topic of couples…What was that Jenny phone call all about?”

“Oh right. Well, Jenny lost her virginity…to a Junior...or soon to be Senior!”

“Really?”

“Yeah, she was all wanting to lose her virginity before going away to college.”

“Seriously?”

“Yeah.”

“Why? Does she plan on being a slut at college or something?”

“I dunno. I think it was just something she wanted to get out of the way in case she meets the guy of her dreams in college or something. You know that first time for a girl is usually not good.”

“And can be messy,” I added.

“Exactly.”

“So who’s the lucky guy?” I asked.

“David…Haber.”

“A friend of hers?”

“No, that’s the weird part. She hardly knew him. You see, this girl we know was having a graduation party and basically invited the whole school. Jenny and David were both there, and bam!”

“A party? Why didn’t you go?”

“Because I wanted to be with you instead,” Parker cooed.

“Well, I can’t fault you for good taste.”

“Ha ha. No, you’re the one with the good taste…the good tasting cum that is.”

“Maybe it was beneficial that you didn’t go. They may not have hooked up if you were there.”

“Hmm, probably not. Most people would just assume that we were together and they'd move on.”

“So you weren’t there and he didn’t move on...he moved in!” I declared.

“Better him than one of those other guys that would have been there. David’s got a really hot ass and he’s kind of cute too. I mean, if he was gay, and I was single, I’d do him.”

“So what you’re saying is that Jenny did good,” I clarified.

“Yeah, and now I’m off the hook,” Parker added.

“What do you mean?”

“Well, Jenny asked me if I’d do it with her…as like a favor.”

“Really?”

“Yeah, over the winter a little bit before I met you, she asked me. I told her I couldn’t. Then she said she didn’t care if I was gay and all of that. She just wanted to get it out of the way.”

“Ooh, speaking of awkward.”

“Yeah, no shit. I had to explain to her that I have to be attracted to the other person to complete the act. And although she’s pretty, I’m not attracted to the opposite sex. I wouldn’t know what to do if there’s no cock? And those flabby milk-filled things just hanging there in the way…what’s with that?”

“Ha ha ha. Spoken like a true 100% homosexual,” I declared.

“I thought she knew that. So why would I want to fuck her…favor or not?”

“Some gay men will have sex with a woman just to see what it’s like,” I offered.

“Yuck!”

“I know this older manager at the store who had been married for like 27 years, had three kids with her, and then told his wife he realized he was gay. I guess he wanted to see if he could make it as a straight man. I always thought he was a little effeminate for a heterosexual. When people would tell someone he was married, the reply would always be ‘To a woman?’ The only person who couldn’t tell he was gay before he spilled the beans was his wife.”

“Twenty seven years?”

“Yup, I guess the years go by quickly when you’re busy being married, working, and raising kids.”

“Ugh, kids! I think that would drive me insane!” Parker exclaimed.

“Yup, once someone has kids, life becomes all about the kids,” I explained.

“I've always wondered if raising children was for people who need something to do. You know, like a way for straight couples to fill up their time between days at work," Parker theorized.

“You make it sound so tragic,” I replied.

“Isn't it? Why would any rational person suddenly think 'I'm tired of sleeping in on weekends and doing whatever I want to do and having extra money to take trips to Europe or the Caribbean. Let's end all of that and have kids!' Makes no sense to me,” he concluded.

“Well, you can add that to my knock on religion,” I added with a chuckle.

“Damn you logic!” he said mock shaking his fist in the air.

(He paused and changed topics.) “You know, at one point I was going to ask you if you’d do it as a favor to me.”

“Do what?”

“Do Jenny. But there’s no way she was ready to take that sausage, so I thought better of it,” Parker conceded.

“So if I had a smaller cock, you would have asked me to fuck Jenny,” I questioned him.

“Sure, I mean, it would be like a one-time thing. It’s not like you’d be getting married,” he explained.

“You mean, I wouldn’t have a say in that?”

“I dunno, I can be quite persuasive. It would be a favor to her because that’s what she wants, and it would be a favor to me because it would get her off of my back.”

I then tried to imagine fucking Jenny. I wondered if I could do it.

“You could probably get it up for Jenny, don’t you think?”

“Yeah, probably. But I think she would be in pain,” I assessed.

“Right, so that’s why I didn’t ask. But now it’s taken care of.”

I wasn’t sure how to feel about the exchange we just had. Parker is my boyfriend. Jenny is his best friend. So he’d be OK with me fucking her so that she wouldn’t be going to college a virgin. It certainly wouldn’t be cheating because it's at his direction. And Jenny wasn’t a bad looking girl, so I could probably deliver the goods, but it would be strange. I guess a fuck is sometimes no big deal depending upon the circumstances.

However, the one thing that Parker was missing in the equation was that Jenny was infatuated with him. I couldn’t blame her because I was infatuated with him. But by some strange twist of fate, I ended up the victor. That didn’t happen very often. But if it was to only happen once in my life, it happened at the right time.

“Oh, and the best part…David went down on her and ate her out before fucking her. Annnnd that got her totally wet!” Parker said breaking me from my thoughts.

“No shit! Really? I’ve slept with girls before, but I’ve still never eaten out a pussy. For some reason, I find it…”

“Repulsive?” he offered.

“Yeah, I guess…for want of a better word.”

“Hmm, but you seem to like sucking cock now.”

“Um, I guess I do. Imagine that.”

“What’s there to imagine? Who would want to put their face in a wet, smelly, sometimes bloody place when you can simply suck on a nice juicy cock? Seems like a no-brainer to me.”

“So Jenny got her first one out of the way. A one-time thing at some party,” I pondered.

"Oh, but get this,” Parker began, “Jenny said she enjoyed it!”

“Really?”

“Yup, and David called her two days later to ask her out,” Parker added.

“So what is Jenny going to do? Are they going to start something?” I asked.

“Yeah, they’ve got the rest of the summer to work it out. Then she’s going to URI in the fall, which is maybe an hour away. So they can still see each other often enough.”

“Well, they won’t be as close as us,” I declared.

“Yeah, I think on top of each other is pretty darn close,” Parker said as he kissed me on the lips.

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