The Pain of a Nineteen-Year-Old Virgin

The Second Go Round

Our bodies intertwined on the big bed during our recovery phase cuddling enjoying sensual touches. Shawn had completed me. As we subtly caressed each other’s bodies my electrified asshole sang out, throbbing with pleasure over pain, wanting more. My bottom whirred, my mind entertaining thoughts of what might come next. I wanted more of him. I didn’t want the evening to end. I didn’t want our relationship to end, but I knew better. All I wanted, to lay next to Shawn forever, kiss his body, inhale his manly scents and wait for him to get hard again. 

Although less than 48 hours earlier my plundered asshole wrecked by that humungous black dildo, Shawn’s cock made me yearn for more and more and more of his seven- and half-inch cock filling my bottom. My partner knew how to use his powerful member along with sensual touches to pleasure me. “I enjoy sex with you Shawn…We communicate our desires well.

“Your touches so sensual,” Shawn said.

“Thank you and same to you,” I replied. 

“You know I discovered a long time ago that communication is key to outstanding sex and relationships,” Shawn said. 

We continued touching each other in a physically gratifying manner exploring each other’s erogenous zones. After minutes of silence Shawn asked, “Do I intimidate you? You know, oppress you in any way because of the difference in our age or who I am?” 

“No.”

“I just wanted to know because of my reputation; you know, my standing in the porn industry.”

“I haven’t given any thought tonight to any of that…I just want to be with you…I want you next to me all night…Forever.”  

“Same here.”

Physically, I could tell time had come to repay my partner for the impassioned pleasure he’d delivered onto me earlier. The ginger porn star began to get restless and erect. As time waned our conversation and cuddling diminished. Shawn became more restless. We’d learned much about each other during our respite conversation. Our likes and dislikes all around we pretty much paralleled, but I detected Shawn wanted more than conversation. 

Once again as we boned up, we began rolling around engaging in casual frotting. After a few minutes Shawn whispered into my ear, “Oh baby eat me and put that big cock of yours inside me…Fuck me with everything in you.”

“You bet…How you want it?”

“Be yourself, just let it play out.”

By then, and maybe because of the pills we were hard and ready to go again. But before I fucked him, we needed to get in some foreplay. I rolled off Shawn to get into position to reciprocate. The redhead pulled his legs back into his freckled chest. My thumbs spread his creamy buns apart exposing his hairless luscious ass crack. Before eating him, I buried my face in his groomed red bush inhaling the manly aroma. Damn, Shawn smelled good.

I sniffed as I began working my way up the mountain to the summit: seven- and half-inches to the top. As I topped the mountain there my eyes met the most beautiful bulbous cockhead I’d ever seen. My tongue began circling the alluring crimson coronal ring while listening to Shawn coo with glee. After a few trips around the ring I noticed a pearlescent droplet of precum beginning to ooze from Shawn’s piss silt. My tongue swept up from the frenulum area over the top to the urethral opening where it scooped up the large droplet of man honey.

Shawn moaned and squealed with pleasure as my tongue made another trip back for more. My left hand surrounded his cock pulling it down a little to give the tip of my tongue a chance to explore inside the opening. Once my taste buds satisfied with his zesty spunk, I returned to his creamy buttock where my tongue sought out his sweet brown eye. 

My partner’s asshole began giving me the brown eye wink. The sphincter began to wrinkle winking at me. My tongue began darting in and out of my mouth the tip of my tongue titillating his asshole. Shawn shrieked and jump. His wrinkled sphincter puckered with anticipation, twitching opening and closing ready with eagerness to accept my tongue deep inside him. I repeated the actions Shawn performed on me earlier, listening to him yowl with glee each time my tongue frolicked around his asshole.

After a few minutes of cooing and moaning Shawn began yelling for me to fuck him. I withdrew my tongue and popped up to see the radiant beauty of Shawn’s face. He said, “Oh baby put it in…Fuck me.”

“You ready?”

“Been ready.”

I grabbed the oil and proceeded to lubricate Shawn’s ass. My finger pushed a good amount of lubricant deep inside. Then I lubed my cock up. I asked again, “How do you want me to take you?”

“Fuck me doggie first and then I’ll roll over…Finish me missionary.”

Shawn positioned his body towards the edge of the bed with his creamy buttock up in the air his head to the side on the mattress. He reached around pulling his buns apart allowing for better target acquisition. Me holding my hard cock in my hand standing on the floor behind him I began inching forward. I could see his asshole winking, inviting my cock to enter. Once the spongy head of my cock touched his asshole he flinched, pushing out and then relaxing. After a couple tires my cockhead popped into the first chamber. He groaned as it popped inside. I stopped for a few seconds before I continued pushing forward. All the while Shawn screaming for me to fuck him.

As I penetrated Shawn’s ass my hands roamed over his buttock and back. With rhythmic movement my cock provoked sighs and then cries to fuck him. I moved forward, reaching around his body my hands found his hard nipples. I twisted and pulled on them. 

“Oh yeah,” Shawn said. “Just fuck me slow and easy…I want to enjoy this for as long as possible.”

“You’re so tight and hot.”

“Oh baby, I can feel your hot cock inside me…Keep playing with my nipples.”

My left hand reached around to take hold of Shawn’s hard cock while my right continued playing with his nipple. I stroked his cock a few times and then felt a droplet of precum on my fingertips. After a few minutes I pulled out and slapped my ginger actor on the ass signaling him to turn over. On his back Shawn smiled up at me with satisfaction. I eased down on top of him our hard cocks touched, and lips met. As we frotted and kissed soulfully he whispered in my ear to fuck him again. I didn’t need any lube, so I began to penetrate his ass.

Once inside I began to set an easy piston rhythm back and forth. I slowed down and eased forward to bite and lick Shawn’s erect nipples. I lightly bit down on them one by one and sucked on them, listening to my partner wail with pleasure. I felt good as a novice that I could bring so much exuberance to the more experienced red headed porn star. Over the years he’d fucked many guys in porn films. Now, me the newbie, bringing pure joy to his life.

Like many of the actors on videos I knew from Shawn’s body language and sounds he wasn’t faking or uninterested. He maintained an erection as I moved in and out of his ass. After a few minutes of kissing Shawn whispered in my ear, “Fuck me…Make me cum baby.”

I knew banging the prostate was key to making him ejaculate with an explosive orgasm, so I hit it with all I had. I moved around in and out hitting it, making Shawn wail, “Oh yes…Fuck me…Right there baby fuck me make me cum.”

With Shawn fucking me back we worked together in unison on his sweet spot. He’s what I’d call an awesome power bottom. He knew how to use his ass to please his partner. I think he knew I might be ready to cum. He said, “Don’t cum until I say so…Think about something else.”

I continued pumping his ass with my mind on playing baseball. Something hard to do with him wailing for me to fuck him. We really got into it we were all over the bed fucking on our sides, him fucking me on top and then me back on top. No doubt the red head knew how to fuck. Finally, he said, “Let’s get it on and cum together.” 

We began fucking in earnest, me hitting his sweet spot hard about every other stroke. Our breathing became labored. Droplets of perspiration dotted our faces and bodies. We were both wailing for each other to fuck the other. Then I felt Shawn’s body tighten and then go ridged as he bucked up into me. His legs surrounding my waist tightened. I could feel the heels of his feet spurring my backside like a cowboy on a bronc. I plowed him with all I had and we both came within a couple seconds of each other. Shawn first. He sprayed spooge all over his face and chest, while I began spraying his lower bowels with my warm jizz.

With the two of us spent, I collapsed on top Shawn. My cock lingered inside his vibrating asshole. We lay like that not moving or saying a word for what seemed like a half hour, but only about five or ten minutes. During that time, he worked his sphincter surrounding my deflating member before it fell from his asshole.

Finally, Shawn broke silence saying, “Let’s go for another bubble bath.”

“Sounds great to me.”  

As the two of us played and splashed around in the Roman soaking tub, for some insane reason, my mind went to my best bud, Phil. Unlike Shawn, Phil’s nipples did not protrude or become erect, but rather were small flat brown dots on his chest. I’d read on the Internet that some guy’s nipples immediately became erect because of weather change or sexual stimulation; whereas, other men’s nipples did not become erect with sexual stimulation, change of weather or touch. 

Like anal intercourse some men found nipple play not to be masculine while others found it to be a major part of foreplay. I remember that day on the loveseat in my bedroom when I had a deep-seated desire to bend forward and take Phil’s cock into my mouth. I wanted to taste it and try to give him a blowjob he would enjoy and want to come back for more but held off for fear of being admonished by him about being gay. I sure didn’t want Phil to out me and tell our friends that I had given him a blowjob, so I said, “Phil, I hope you won’t tell anyone what we’re doin here today.”

“You kiddin, I ain’t gonna say word about this to nobody…Hell, you know I ain’t no queer…But you know this sure feels great.”

“Thanks. So, this will be our secret.”

“You bet,” Phil said. “Take it to our graves.”

We continued to stroke each other using Jergens lotion as lubricant. I didn’t want the experience to end. I enjoyed playing with my best friend’s dick. I thought to myself that maybe later I could work up the courage to approach him about us trading blowjobs. After what seemed like hours both of us exploded: powerful orgasms that produced huge amounts of jizz that shot all over our abdomen and chest areas. I got up to get a warm washcloth from the bathroom to clean up. 

Phil and I engaged in about a dozen more secret mutual masturbation sessions over the next few days. The times in the shower together after swimming all I could think about under the waterfall: sex with Phil. As we moved around inside the small shower stall our wet bodies touched on occasion; our hard dicks brushing against each other’s bodies and buttocks. 

The touching always sent shudders of pleasure throughout my body. One-time as Phil stood behind me in the shower, I could feel his hard dick positioned at the bottom of my ass crack as he reached around to stroke me. He never knew how much I wanted him to take me that day, shoving his cock all the way up my ass. 

I daydreamed about his seven inches of soapy steel hard schlong sliding up my ass and then he’d have me bend forward placing my hands on the shower surround, so he could continue to piston his cock in and out of my soapy ass to completion. I imagined hot cum shooting from his cock coating the insides of my bowels. I dreamt about him slow fucking me night after night. Maybe that was the root of some of my surrealistic dreams, something I wanted so much, but something I knew could never come to fruition.

“Hey where you at bud?” Shawn asked, nudging my semi-erect cock with his foot.

“Nowhere,” I said. 

A little white lie. I couldn’t tell Shawn sitting across from me I had been thinking about another boy. Shawn took my foot and began caressing and kissing it. I moaned with pleasure. After a few minutes on my feet he got up, turned around and sat down with his back to my front and said, “Play with my nipples and cock.”

The ginger porn actor didn’t have to ask twice. My arms moved in beneath his armpits surrounding his body. One hand playing with his nipple and the other stroking his cock. Shawn moaned passionately. I kissed him across his shoulders and neck while every once in while changing hands.

Shawn began a conversation. “Ran, do you think you’re bi-curious or gay?”

“I don’t know what I am…Haven’t figured it out yet.”

“You told me you’ve got a girlfriend in college, just wondering…How many men have you been with, besides me?”

“What do you mean by that question?”

“Randy, it’s a simple question…How many men have you made love with like we’re doing today?”

“You’re my first,” I said. “But I’ve fooled around with my best buddy and had sex using dildos while watching porn actor like you.”

“So, I got your cherry…Took your virginity.”

“Yeah, I guess so.”

“So far how do you like being with a male over a female…In a sexual situation?”

“Man, I’m impressed…I like it and I like you.”

Shawn stood up in the tub his wang standing proud. “Come on I want you to fuck me again.”

We got up dried off and went to the bed. Before we exited the bathroom, Shawn gave me another pill and he took one. Once in the bedroom, we got into a sixty-nine position and began sucking each other. I could taste Shawn’s precum. My hands roamed over his creamy smooth buttock while I sucked his cock. Shawn called down to me saying, “You ready to fuck me baby?”

“Sure”