Chapter 6

When I woke up, I was a little confused and disoriented when I found myself in a strange bedroom. It took me only a second to remember where I was and why I was there. I looked over beside me on the bed and saw Jennifer laying next to me. Her long dark curly hair was splayed out across her pillow as she snored a soft cute little snore. I smiled as I reached over and caressed her naked body. Jennifer’s eyes fluttered open and when she saw me, she smiled.

“Good morning sexy.” Jennifer said softly.

I smiled even bigger. A girl as hot as she is has never called me sexy before. “Good morning.” I said back to her.

“How long have you been up?” Jennifer asked.

“Only a few minutes.” I replied. “When I woke up and saw you next to me, I thought I was still dreaming.”

“Oh yeah? Why is that?” I asked.

“I’m not the kind of guy that girls like you think are sexy and want to be with. I’m not a jock or a stud or anything like that.” I said.

“You don’t give yourself enough credit Jack.” Jennifer said. “I bet plenty of girls find you sexy. And I can testify for a fact that you are definitely a stud.” She ran her hand across my bare chest, circling each of my nipples once before pinching them and sliding her hand down to my belly and resting it just over my belly button.

I could feel my cock growing harder and harder by the second. I saw Jennifer smile, and then I felt her hand grasping my cock and I moaned.

“I don’t care if anyone else thinks you’re sexy or a stud, I do. And I’m going to prove it.” Jennifer said and then she whipped the covers off us. The next thing I knew Jennifer bent over and engulfed my cock in her mouth. When she was satisfied my cock was as hard as it was going to get and wet enough Jennifer pulled her mouth off my cock and then threw her leg over me. With her hands resting lightly on my shoulders for balance Jennifer positioned her pussy over my cock and slowly lowered herself down on it.

“Oh fuuuuuuck.” I groaned as the hot tight wetness enveloped my cock. I reached up and squeezed and massaged her breasts as she rode me and then I sat up a little and sucked on her nipples one at a time occasionally nibbling on them or flicking them with my tongue. I could feel Jennifer’s pussy squeezing and releasing my cock, massaging it as she rode me. I started thrusting up to meet Jennifer’s downward motions. Her riding got more energetic, harder and faster. I let my hands slide down her body and gripped her ass helping guide her motions.

When I couldn’t take it anymore I rolled us over so that I was on top and we were more or less in the missionary position and I started pounding my cock in and out of her pussy as hard and fast as I could. Jennifer moaned loud and deep as my cock penetrated her pussy to its silken depths over and over again and again. She reached up and and grasped my nipples in each of her hands and began pulling and twisting them. I felt my cock twitch with the pleasure/pain of it and driving me closer to orgasm.

I knew Jennifer was having back to back orgasms as I pounded her. She had already had half a dozen orgasms riding me and just as many since I flipped us over.

“I’m gonna cum soon.” I said urgently.

“Yes baby, give it to me. Give me your cum. I want it deep in my pussy.” Jennifer said.

“Oh god.” I said. Hearing Jennifer say that pushed me over the edge and I felt a tingle that started at the tips of my fingers and toes and rushed inward until it reached my core and erupted from the head of my cock, flooding Jennifer’s pussy with rope after thick rope of my cum. By the time it stopped, and I pulled out, my cum was overflowing and leaking out of her pussy as she lay there panting. I watched mesmerized for a few moments as the viscous white fluid slowly ran out of her pussy and down the crack of her ass. My cock was so covered in our cum that it looked like a glazed doughnut and was not even close to getting soft.

“Get on your hands and knees.” I said.

“Damn, you’re gonna be the death of me.” Jennifer said as she moved into her desired position.

I wasted no time and rammed my cock deep into Jennifer’s pussy making her grunt and then moan. “Oh fuck! So deep. You’re so fucking deep inside me.”

I grabbed onto her hips and used them to pull me into her harder and faster. I was pretty sure I could feel the head of my cock hitting her cervix on my really deep strokes. “Fuck! Fuck yes! Oh baby, fuck me hard just like that!” Jennifer cried out. Our bodies were crashing together so hard and fast it almost sounded like applause. I was fucking her like a machine, like a possessed machine. I was breathing hard like I was running a marathon, sweat covered my body and was dripping down my face and landing her back and ass. My orgasm snuck up on me.

“Oh shit!” I said when I felt it surge up out of nowhere. I drove my cock deep inside Jennifer and held it there, my body pressed tight against her ass as my balls unloaded deep inside her for the second time since we woke. With the head of my cock pushed tight against her cervix and my cum spraying against it, Jennifer shot into orbit with a powerful orgasm. I could feel her pussy pulsing around my cock as her orgasm overtook her body. Jennifer’s arms and legs slowly slid out from under her until she was laying flat on her belly with me more or less on top of her. I pulled my cock out of Jennifer and rolled over onto the bed beside her as she flipped over onto her back. We were both breathing heavily as we lay next to each other.

“Fuck, I think you’re trying to to kill me with that beast. It felt like you were trying to put your dick through my forehead.” Jennifer said.

“Sorry.” I said sheepishly.

“Don’t be, it was hot as fuck.” Jennifer said.

“Cool.” I said.

“I wish I had known you a year or two ago.” Jennifer said.

“Me too.” I agreed.

After a quick shower we got dressed and Jennifer treated me to breakfast. She drove us in her car, newer Hyundai Sonata. Just as we were finishing up our meal, I got a text from Bill.

Bill: “R U free to play tonight??”

“Who’s that?” Jennifer asked curiously.

“My friend Bill. He wants to know if I’m up to play tonight?” I said.

“Play what? Softball? Cards? Video games?” Jennifer asked.

“No. He means am I free for sex.” I half whispered, not wanting anyone nearby to overhear.

“Oh.” Jennifer said.

“I’m pretty sure I’ll be busy though.” I said.

Jennifer smiled. “Does he use you like the guy I saw you with?” She asked.

“Yes and no.” I said.

“Alright, that clears it up. Thanks.” Jennifer joked.

“Sorry. Yeah, he uses me, but unlike the guy at your place he makes sure I cum too.” I explained.

“Okay. Would you like to get with him?” Jennifer asked.

“Not if I have to give up my time with you.” I said.

Jennifer smiled again. “Think he’d let me watch or maybe even join in like I did with your other friend?”

“I don’t know. I guess I could ask.” I said. “Do you want me to fuck him?”

“I’m not sure. It was really hot watching you get fucked while you ate me out. Hell, it was probably the hottest thing I’ve ever done.”

“Bill’s pretty cool. He might be okay with it.” I said.

“Ask him then I guess.” Jennifer said.

“Okay, I’ll text him and see what he says.” I told her.

Jack: Maybe. Would you mind if my girlfriend came and watched or maybe even joined in?”

We sipped our drinks as we waited for Bill to reply and see what he would have to say.

It took a little less than five minutes for us to get Bill’s reply.

Bill: “Sure, bring her.”

I looked across the table at Jennifer and she nodded.

Jack: Cool. “When and where?”

Bill: “My place around 8. That ok with you?”

I looked up and across the table at Jennifer again. Once again, she nodded.

Jack: “Ok we’ll be there.”

Bill: “Cool.”

Jack: “Need me to dress any particular way?”

Bill: “Nah. Gonna have you naked in less than 5 mins. Lol”

Jack: “LOL ok.”

“Sound like we’re going to have a fun night.” Jennifer said.

“Yeah it does.” I agreed.

“We need to go shopping.” Jennifer said.

“We do?” I asked.

“Yep.” Jennifer said.

“For what?” I asked.

“You’ll see.” Jennifer teased.

Jennifer drove us to an adult book and toy store. We went inside and we looked around for a while. About an hour or so later we left the store with five new purchases. Jennifer had bought a sexy strap-on harness, it was black with a red ribbon up the back like it was a corset. She bought a couple of dildos to go with it, the first one Caucasian colored and was eight inches long and about as thick as my own cock. The other was dark brown and about ten inches long and nearly twice as thick as the other one. She also picked out a third dildo that was a blue strapless strap-on. The last thing Jennifer bought was a nice thick cock ring. She had wanted to get some lubricant too but wasn’t all that happy with what the store had to offer.

“I can get some Astroglide at the grocery store for half the price and it’ll work twice as good.” Jennifer said.

I just shrugged my shoulders and said, “Okay.”

Our next stop was the Victoria’s Secret in the mall. She bought a sexy red lace teddy that snapped closed at the crotch. She had tried it on at the store and flashed me a peak from the dressing room. She looked really hot. After that we made a quick stop by my place and picked up the clothes I usually wear when I hook up with other guys. Jennifer seemed to like my place although she did say it needed a girl’s touch.

Before I knew it, it was time to leave for Bill’s house. Once again, I let Jennifer drive. As we pulled into Bill’s driveway and she put the car in park Jennifer said, “Just so you know, if your friend doesn’t get you off for some reason, I’ll take care of you.”

“Awesome.” I said with a smile and as I stared to get out of her car, Jennifer’s hand on my arm stopped me.

When I looked back at her she said, “And even if he does get you off tonight, I’ll still take care of you.”

“Really awesome.” I said with an even bigger smile.

Jennifer chuckled and followed me up to Bill’s front door where I rang the doorbell. I looked over at her as we waited for Bill to answer the door. She was wearing a pair of light blue denim booty shorts and a loose T-shirt and some sandals. In her hand Jennifer held a large purse. I knew two things that you couldn’t see just by looking at Jennifer, one was that under her T-shirt and shorts she had on her new sexy red teddy. And two, other than her wallet and our cellphones the only things in her purse were the toys she had bought earlier in the day plus a large tube of Astroglide and a small but powerful vibrator.

The door opened breaking me from my thoughts. “Hey, come on in.” Bill said. He was dressed similar to me in a pair of loose shorts and a t-shirt.

Jennifer followed me inside as Bill held the door open for us. Bill’s place looked just as it had before, tastefully decorated, but clearly a man’s home. I made a quick introduction between Bill and Jennifer.

“Nice to meet you.” Bill said to Jennifer, and then he looked at me and said, “You’re wearing to many clothes. Get naked.” I smiled and stripped out of what little clothing I was wearing and tossed it onto a chair by the door, and then Bill led us into a guest bedroom. “I’d have you strip too, but I’m not into women. But if you should feel the need, feel free.” Bill told Jennifer as we walked into the bedroom.

“Alright, Thanks.” Jennifer said, but she kept her clothes on.

Once we were in the bedroom, I noticed two things, a large queen-sized bed with a large round/cylindrical pillow on it and a comfortable looking chair in the corner of the room near the head of that bed.

“Jennifer, you can make yourself comfortable in that chair while I show you what a cock slut your boyfriend is.” Bill said.

“Sounds fun.” Jennifer said and then she went over the chair and got comfortable.

“Get on the bed, doggy style. Hips on the pillow.” Bill told me.

I positioned myself on the bed as directed and felt my adrenaline as Bill went around to each of the four corners of the bed and pulled out a black nylon strap with a soft wrist/ankle cuff attached to it from each corner. I saw that the cuffs had a Velcro closure as Bill fastened them to my wrists and ankles. Once he was done with that Bill slipped a blindfold that looked like a satin sleeping mask over my head and carefully positioned it over my eyes. Unlike a lot of these types of masks, this one was really good and didn’t let in any light whatsoever. I could feel my cock getting hard in spite on my nervousness.

“I think he likes it.” Bill said. “Want to see?”

“Sure.” I heard Jennifer say. And then I heard the chair creak slightly as she got up and walked over. “Oh yeah, he definitely likes it. He’s already dripping precum. I might have to add this to our list of play options.”

“Mmmmm.” I moaned when I heard her say that.

“Why the blindfold?” Jennifer asked as I heard her sit back down in her chair.

“Our guests like the idea of him not being able to see them.” Bill said as he stripped out of his clothes.

I felt Bill climb onto the bed behind me and then there was a slight sting as he gave my ass a light slap. “Such a fucking sexy tight ass.” Bill said.

“Oh, hold on a second.” Jennifer said.

The next thing I felt was her hands on my cock and balls as she slid the cockring onto me.

“That’s better. Don’t you think?” Jennifer said to Bill.

“Oh yeah. I like it.” Bill said.

The next thing I felt was one of his hands on each of my ass cheeks, and then he spread them apart and then I felt his mouth on my asshole as he started eating me out with gusto.

“Ohhhhh.” I moaned in pleasure. Having recently found out that I absolutely love having my ass eaten this was a nice and very welcome surprise. I felt Bill’s stubble scratching my ass cheeks as Bill ate me, which only turned me on even more. I moaned like a whore as Bill deep tongue fucked me. Every so often he’d reach between my legs and give my cock a couple of strokes. Not anywhere close enough to what it would take to get me off, but it teased me just enough to drive me wild.

“That’s so fucking hot.” I heard Jennifer murmur.

Bill ate my ass for quite a while as I was moaning and moving my hips around unconsciously. When he finally stopped, I was literally panting with desire. I felt the bed shift as Bill maneuvered himself so that he was now in front of me between my arms with his cock right in front of my face. I felt Bill’s hand on the back of my head pushing it downward. He didn’t say anything, but when I felt his cockhead bump against my cheek, I knew what to do. I turned my head to the side until I felt the tip of Bill’s dick slide over my lips. Then I opened my mouth and took his cock into my mouth and started sucking it. I loved the way a cock felt in my mouth, the hard shaft between my lips and the soft head brushing against the roof of my mouth and occasionally pushing back into my throat.