John's Options - Boss or Threesome? Ch. 03

"Wow Ash. You look like Melissa Miller in that thing." Becca exclaimed with pure shock.

"Who?" Ashley asked.

"Melissa Miller. She was on the cover of Sports Illustrated and a Victoria Secret model. You may want to go into becoming a model, or at least a good porn flick." She stated with a solid sense of seriousness, but sarcasm in the end.

Ashley giggled at her remark, and started to strut around with her little outfit. We all started to laugh with her and she was smiling in laughter too.

She fell back down on the bed with me at her side and she asked, "What are you doing silly? You haven't gotten dressed or anything."

I guess she was right. I couldn't just walk over there naked. I responded, "What do you think I should wear then? I didn't bring a teddy like you?"

"Well what did you bring?" Ashley asked while hopping back up off the bed and walking over to the closet. She opened it up and found my bag on the floor. She bent over exposing her ass under that teddy, in order to grab her bag. I just got jealous again thinking of how John was pounding it a minute ago, and she had such a perfect curve he was in heaven hammering that cushion.

I was so skinny and small; I knew he wasn't going to enjoy doing me like that. I started thinking about him and how he'd prefer the other girls over me. I got scared.

"Well, I've always thought you looked the hottest in your workout outfit." Ashley said as she pulled out my tight lycra short shorts, and my sports bra.

"No Doubt. Your body looks so tight with this on, not to mention it showing off your perfect abs.

"Who cares about that? Fuck, you girls have all the good shit. Ashley over there, looking like a Victoria Secret Model, and Becca with curves going on for days. I'm just a fucking rail. I look nothing like you girls!" I frantically complained.

"Lori, you heard what he said. He thinks we're all tens and in case you didn't notice, he had an opportunity to take me, but he chose you instead." Becca emphasized trying to calm me down.

I felt a bit better recognizing that she was right. I also began to think about how he did love kissing me in a passionate way and he did love the blowjob I gave him moments ago.

"Whatever. I guess I'll wear the stupid thing." I responded with anxiety, but knew they were right.

Whenever I went running in that outfit, cars would honk at me, and guys would always stop what they were doing to check me out. One time two guys were walking by and they both walked into a gutter full of muddy water not paying attention to anything but me.

Ashley tossed them on the bed and began grinning with her teeth biting her lower lip again. She was excited for me, and I was pleased to know she was.

I stood up and stepped into my shorts, which clung to every inch of my small juvenile ass, and then put my sports bra on.

"Honey, he's going to be drooling over you in that. Don't be worried, just go enjoy yourself. After all this is the last thing your virgin ass is ever going to wear." Kate supported me and encouraged me to go and have fun.

The attempt worked well and I began to feel confident again. I saw myself in the mirror and my long tanned legs and firm butt were mesmerizing. I promised myself to remember myself in this image and to be the confident girl I knew I could be.

Ashley gave me a big hug and came back to look me in the eye. She told me, "I'm proud of you to have the courage to tell us you're a virgin, but don't let that make you nervous. John's amazing and I know he'll take care of you, but it's gonna hurt. So just relax and take it all in. After a bit, it'll begin to feel great."

I gave my friend a big hug again, and asked, "Well, he's been with you, how soar are you feeling right now?"

"Like someone drove a Mack truck inside me." Ashley said laughing.

Her humor made me feel comfortable about the future. If she felt like that and loved it, I guess I could feel the same way too. I went and sat down in the other chair with Kate. I took a couple sips of Champagne with her and she just smiled with me relaxing.

We waited a few moments as I starting thinking about all the things I would do with John. Many nice thoughts crossed my mind, but the most reoccurring thought was what the feeling of him inserting that monster into me would be like. I was getting wet from the anticipation. How much longer was it going to take?

Becca decided to put some clothes back on as well and she got up from the bed and found her panties and a tight fitting yellow t-shirt from her suitcase. Then after she got dressed she walked over to the door and began to look out the peek hole.

"Sorry. He's not in the hall." Becca informed me with disappointment.

I was getting anxious as 10 minutes went by and still no sign of John. I drank another glass of Champagne and the girls joined in as well. They were involved talking about how John's cock felt in their mouth. The big discussion was how Kate was able to swallow the whole thing. I was very impressed, but I could only stare at the door waiting for him to come.

Finally, another 5 minutes went by when the phone to our room rang. Ashley was closest to the phone and answered it, "Hello, Handsome."

I couldn't hear what was being said we could only hear Ashley.

"We've been wondering where you were. Are you coming up?"

"Oh. Okay, well I'll put her on." Ashley held out the phone in my directions. Once again with a nice smirk on her face.

As she handed it to me she whispered, "Go get him Tiger."

"Hello." I asked. Clearly knowing it was John, but unaware of what was happening.

"Sorry to keep you waiting. I know that mustn't been easy."

I gave a simple little hmmm sound letting him know he was a little bit right.

"However, I'm ready if you are. I just need you to come out and knock on my door to room 203. We have it all to ourselves and the girls will be right next door."

"Can they hear us?" I asked curious to know if my privacy would be broken.

"That'll all depend on you." And I could here him smiling through the phone.

I gave a small chuckle and responded, "I guess so. Well, I'll be right over" and I hung up the phone.

I didn't waste much time. I looked back at the girls and asked how I looked. They all gave me positive remarks about certain features. Kate told me to tie my hair up into a pony tail. It'll give him something to grip.

I liked the idea so I grabbed a hair tie and did just that. They all gave me one last look and told me to have the time of my life.

I stepped into the bare hallway and could only hear the ice machine from across the hall. It was echoing fairly loud and you couldn't hear any sounds coming from inside the rooms because of it.

I stood in front of the door and gave a light knock. The door opened, but I couldn't see John. He must have been standing behind it. As I stepped through the door way I could see inside the room and it was lit up with a dozen candles. It smelled like warm vanilla throughout the room.

I peered around the door and found John holding the door in a pair of black Calvin Klein Sweat Pants. His bare chest had the reflection of the candle light flickering off his muscles. He had a small developed six pack and his arms looked larger to me now. Maybe it's because he was alone with me.

I took my final steps inside and allowed him to close the door. He stepped behind me and wrapped his arms around my waist. I let the back of my head fall into his chest as he walked me into the room. It had a large King Size bed rather than the two beds we had next door. There were two candles, one on each side of the bed to give it a nice romantic glow.

"I take it this is what you were doing with all the extra time?" I deliberately asked.

"I thought you deserve it. Don't you?" He asked back.

"No argument here." I responded and turned around at the foot of the King Size bed, to face John.

He stepped back and looked at me from head to toe. Quickly he acknowledged me, "If you're running around in that outfit, you must be causing car accidents."

I smiled and gave him a sexy pose, crossing my legs and putting my hands on my hips. "Especially when I do this at the traffic lights" I emphasized.

"So how do you like it when they respond like this?" John asked leaving the moment open. He walked towards me and reached down grabbing me by the sides of my short shorts, and started to kiss me.

I reached up and held his cheeks with my hands as we kissed. Then I reached around him and played with his hair as we continued to make out. It felt much closer and more intense as we were alone in the room. I wasn't posing anymore and he was slowly moving his body into mine. I was running out of space quick, so I just fell down onto the soft bed and waited for him to follow.

I love lying there after with my tight fitting workout clothes. Watching him stare down at me I could see his animal instinct begin to take over and lust for me.

"You know, I'm actually shocked you're still a virgin. Being in that room, I thought everyone would have to have a little bit of experience. You have some heart, but why are you?" he asked as he leaned his knees into the bedside to support some weight.

I stayed lying on the bed and answered, "My boyfriend and I have fooled around orally, but he never really made a move to go for it. I get looks from plenty of boys in school, but word got around that we were involved and just assumed we were doing it."

I pulled myself up to grab his sweatpants drawstring and began to untie the knot and continued, "Not before long I guess I didn't care and assumed the time would come soon. However, tonight the feeling I get from being around you and the girls, hasn't matched a thing I've felt being with Mike."

I finally got the knot loose and I slid his pants down to let them drop on the floor. His cock popped straight up at me after the elastic band slipped down and a little clear bit of cum was still oozing out.

I licked the little bit of semen from his dick and laid back down on the bed and finished, "Truth is. I'm scared shitless right now but I know you know what you're doing and I hope I can be just as much fun as the other girls. But when I think about that thing being inside me. Wow!" I gave a little cringe and stared up at him awaiting his move.

John moved his hands onto my body as he gave me a small kiss on the forehead and a few on my neck. As he did so he explained, "Well, lets just make this as memorable as possible for both of us, and believe me, I'm never going to forget you either."

"Why's that?" I replied with a smile.

"Because you're fucking hot as hell and I mainly I haven't taken a girls' virginity away ever." He encouragingly responded back.

"Oh I see. So maybe you're not the guy for me." I playfully responded as he was now lifting my sports bra top over my head, exposing my perky breasts. I dropped my chin downward to watch him begin kissing my chest and sucking on my nipples. I began to feel my blood pump and my breathing increase immediately.

John was so gentle with his lips brushing against my skin. He was massaging every inch of me as him hands were also rubbing my back with his fingertips. They were swirling in circles slowing making their way lower down to my bottom.

I began to feel loose and relaxed. Along with that my juices began to flow and I could feel the moisture building up between my legs.

John had me completely seduced as the next minute went by and then I felt his fingertips now peeling my tight shorts elastic band down.

John stood back up standing about me again, but he grabbed my shorts on both sides and had a big smile on his face. I grinned back at him biting down on my lower lip trying to prepare for that monstrosity to enter me. Speaking of which, I couldn't take my eyes of it now, as he stood there with it pointing shaft sticking straight out from his body. His balls were nice and tight in his scrotum and I began to think of what they were going to feel like when he was thrusting this thing deep inside me. Shit! How could this feel good? I began to get nervous again, but I was still wet and his touch was so stimulating.

His hands peeled my short shorts down and he found his surprise all nice and moist for him. The small triangle of pubic hair was nicely trimmed.

"Damn, you're so fine how did I get so lucky?" John asked in a very complimenting voice.

I wanted to let him know how I felt though so I responded, "Right now I feel like the lucky one. You're so gentle and sweet. Most boys aren't."

"Fair enough. I have one other thing to make things easier." John stated. He pulled out a travel size bottle and poured whatever it was into his hands. He then rubbed it on his foreskin and stroked it all down his pulsing cock. I could then see the candlelight reflecting of his skin even more. Obviously it was KY gel, or something to that regard.

"I don't like to be called easy though." I joked.

"It's going to make it easier for you though. I don't know what your about to feel, but I don't want anything to hurt. I'm going to love this and I want you to as well." He sincerely responded.

"Well time to get fucked I guess." I continued to joke with a smile on my face and I scooted up the bed to come to rest on the pillows.

John chased after me on all fours across the bed.

When he his face was even with mine I reached up and grabbed his biceps pulling him in to kiss him. We were tongue tied and not focused on the kiss but more about his cock positioning itself against my young pussy. He had aligned the head of his penis right at my entrance. My lips were melting to the touch of his mushroom head pecking the pores of my skin.

John pulled back and said, "Okay, here we go."

I closed my eyes and tried to focus on how good everything was feeling. In that moment I began to feel the push. That mushroom head began to feel like a jaws of life opening me up. I let out a tiny squeal as he was able to insert the head.

"It's okay, this is the hardest part. After two minutes your body will get used to it." He reassured me. I believed him and nodded as I looked him in the eyes. He gave a smile and looked back down my body. I closed my eyes again preparing for more.

His shaft was beginning to make me understand why they called it screwing. It felt like he was drilling for oil and determined to find it. I could feel my pussy beginning to open more and more. He was taking his time thrusting quite softly, but with enough pressure to keep expanding my vagina.

Then I felt something inside me rip. It felt like a wall crashed inside me and his cock was the battering ram. His thrusts began to get a little deeper with it. I wanted to cry from the initial pain, but didn't want to ruin the moment. I just kept my eyes closed and bit my tongue to deal with the pain.

"That was the hard party baby. That was your Hymen breaking and basically you've now lost your cherry." John smiled at me and allowed me to gather myself. He kept his cock in me and was flexing it somehow. I could feel his pulse inside me. It was extremely stimulating. I hurt, but began to want more.

"Am I bleeding?" I questioned, realizing that if my cherry was gone I might be a mess.

He pulled his dick out and we saw a little bit of red, but nothing as bad as I thought I could be.

He wiped it off with the pillow on the corner, and then positioned himself back between my legs. I spread them more open to send a nice invitation to carry on.

John got right back on top and slid his member back into me where it was before. It went in much easier this time. Almost as if he had drilled a hole and he had plenty of room to continue.

John found more of me to screw quickly, however, and I could feel his head pushing me open again.

The head kept spreading my pussy wide and I could feel the barrel of his shaft keeping me engorged.

I wrapped my legs around his waist as it felt like a better position. My ankles rested on the tops of his buttocks and I could pull him into me whenever I felt comfortable. Each thrust was slightly longer and after a couple minutes I finally felt his balls slapping up against my bare ass and I realized it was over. He wasn't going any farther, and Thank GOD! Because I don't know how much more I had left in me to offer.

John was moaning now as the heat was building between both of us. I was moving with his thrusts now and that lube was greatly appreciated. He was sliding completely in and out of my pussy.

"Holy Shit! This is insane." I cried out in pure humility and passion. This boy, or young man, was pounding me like I was a piece of meat needing to be tenderized. The repetitions were moving from medium speed to fast, and I could feel his cock reaching the deepest wall of my vagina on his longest thrusts.

John was moving his hips with a twist that got me moaning a bit more with each motion. I could begin to feel stimulation that I had never felt before. My back was arching to push into him more.

"You like that don't you?" John exclaimed as he fucked me.

I replied immediately. "Yes. Ughh. Keep going."

John lifted my hips up with both hands on my waist and got a perfect angle to nail my G-spot. I'd played with myself a few times, but never did it feel like this.

"Right there. Yes. Please. Please. Yes....." I kept panting over and over.

"Yeah. Take it you little slut. You've been waiting for this your whole life. Now take it." John became an overpowering force that I couldn't oppose, even if I wanted to.

The sweat from his body I could feel sticking against my inner thighs as I wrapped them around his waist tighter.

"Fuck me. Yes. John. Yes. Oh God." I was erupting in pleasure as this pressure was building inside me.

He grabbed my neck with his left hand and held his body up with his right. I felt imprisoned to this bed while he defiled me.

My small tits were erect and bouncing up and down with each penetrative jab. I rolled my hips with his rhythm and my vagina was now an open tunnel. The muscles that had never been used before were very soar, but the pleasure outweighed the pain. I stared into his eyes and could see he was in the home stretch. So was I as I had reached my limits and began expressing a whole new sensation."

"John. Oh God. John! John!!!" I exclaimed as my juices began pouring out my pussy lips.

"Take it Lori!" John yelled as he was now at his fastest thrusts with his balls slamming into my ass.

"Fuck. Yesss!!!!" I exclaimed. And gave a deep breath of relief as he was about to climax himself. This orgasm was absurd.

"Get Ready." John told me but I had no idea what exactly he was thinking. Then as he made one last plunge deep into me I saw him pull out and raise himself up above me. John stroked his cock rapidly a foot above my face and I just watched expecting his load to shoot out.

I didn't want it to make a huge mess so I opened up my mouth as a target and let my tongue hang out a bit.

"That's right. Good girl." John complimented my action.

After that second his moan built up and out it came. Cum sprayed wildly across my nose and forehead. I think some went into my hair. He then dropped the head down onto my offered tongue and poured the rest out.

I tasted the chalky flavor of his cum and the sour taste that must have been me. It was a very unpleasant taste, so I licked up the remainder slowly dripping from his cock and swallowed it. I reached up while still on my back to pull his cock into my mouth. I got both hands on it and I shoved it into my mouth. It was really hot and a few last drops were making their way out.

I looked up at his face as I graciously finished him off. I was so grateful that this wasn't horribly painful. I actually had an orgasm, unlike many other friends of mine that have shared one and done moments with me.