My Life Pt. 02

"I wasn't sure if I should do this" he said hesitantly.

"It'll be fine," I said laughing, "I'm Italian; I've been drinking wine with dinner since I was eight."

Throughout dinner we talked fairly easily about all kinds of things. We both loved Shakespeare, which he said, with some embarrassment, made me one of his best students. I'm not sure what was embarrassing about that, I guess the reminder that I was his student.

After diner we went and sat on his couch and talked a bit more over another glass of wine. Then we kept looking at each other, neither of us knowing how to start. An awkward silence fell over the room.

I couldn't look him in the eye for some reason. I was fairly sure we were on the same page, but someone needed to make a move. I saw his hand resting casually on his knee. My legs were tucked under me and my bare knee was maybe an inch from his. I had to break the impasse; I gently took his wrist and moved his hand to my knee. He allowed me to and when his fingers touched my bare skin it sent thrills through my whole body.

I looked up and met his gaze. He really had lovely eyes behind those glasses. I took them off for him and folded them, setting them on the coffee table. I looked at him again. Now there was an intense gravitational field pulling us together. Before long we were kissing passionately. We did this for a long time, hands tentatively exploring each other's bodies.

Then it started to get intense. His hand slipped under my top and started caressing my breasts and playing with my nipples. My hand was caressing his hard cock through his pants; I had to adjust my position multiple times to accommodate my cock getting hard.

Then he was on top of me, my top pulled up exposing my right breast, my skirt was hiked up around my waist. I could feel his cock pressing against my inner thigh as we made out and groped each other. It felt amazing but if he kept at it he was going to dislocate my hip. I had to push him off.

"I'm sorry did I do something wrong?" he asked, genuinely concerned.

"No, I was just uncomfortable" I said.

"Maybe you should show me your bedroom" I suggested.

Doing it

He held my hand as I followed him down the short hall to his bedroom. Once we got into his room we both got shy again. There was an awkward moment as we both tried to move together to embrace but ended up blocking each other. Then I just let him take the lead and we were kissing again standing next to his bed.

My heels put me at a good height for kissing while standing and it wasn't long before the intensity was back and we were grinding against each other as we made out. It was getting really hot before long and my heart was pounding in my chest and I was really nervous.

The thing is that I knew or hoped we would end up this way. I hoped I knew what was coming next, but this was still my first time and a part of me was afraid of what was to come.

His hands found their way down to my butt and were caressing me and pulling me rhythmically against him. Both of our cocks were hard as we pressed against each other through our clothes. We were moaning into each other's mouths as we kissed and the intensity was building. I could feel him building too. We needed to stop or we would be cumming in our clothes right there and then. As hot as that sounds, we had time and there is so much I wanted to do.

I moved my hips back away and he let me up, breaking the all too electric contact between our cocks. I took a half scoot back and pulled my top over my head. I want to say it was seductive and sexy, but it caught in my hair clip and I had to struggle a bit. After I got free I took my hair clip out and let my hair fall free. It fell over my shoulders, just shy of covering my breasts.

I looked up at him sheepishly. He had said he was bi, but I still wasn't sure how much he was into girls or how attracted he was to me specifically. He was staring, his mouth half open, unmistakable lust in his eyes. I breathed a sigh of relief.

I moved forward and started unbuttoning his shirt while he looked at me. His hand moved slowly, tentatively to my breast and started to caress me as I worked his shirt off of his shoulders.

He was a bigger guy and based on his complexion I wasn't really expecting how hairy his chest was. Both of us were shirtless now and I moved into his welcoming warm embrace, my breasts pressed to his bare skin just below his chest. I held my cheek against his chest hair.

If you had asked me before this moment I would have said hairy men didn't really turn me on. He did. He was perfect and it just felt so wonderful. I felt his cock straining at his pants and my fingers sought his belt buckle. I fumbled with it for a minute before getting it open and then unbuttoning and zipping down his pants.

I moved down his body, my nipples grazing over his belly as I fell to my knees and pulled his cock out of his boxers. I looked up at him as I stroked it, I looked it at. It was beautiful. About six inches long, circumcised, it felt smooth, soft and velvety and yet very rigid. I looked back up at him as I took it in my mouth.

I was in heaven sucking this cock. Such a beautiful cock attached to a beautiful man. I was getting emotional about it as I felt him thrust a bit into my warm wet mouth. He let me suck him for just a bit before stopping me.

"I want to see you" he said, looking down at me.

He helped me to my feet and then he laid me back on his bed with my legs hanging over the edge. Then he slid his hands under my skirt, over my hips and started to pull down my panties. I lifted my hips off the bed as he slid the down my thighs. I kicked my shoes off as he took my panties all the way off.

Then I was laying there completely exposed. I was naked except for my thin skirt as he stood between my legs looking down at me. He was so big, tall and towering over me. My heart started pounding uncontrollably as I looked up at him. I was starting to feel self-conscious as he gaze raked over my body.

Then he lowered himself on top of me and began sucking and caressing my breasts. My cock was pressed against his belly and I couldn't help rubbing myself against him as my back arched and I moaned. He started kissing his way down my flat tummy, his hands sliding up my thighs, taking my skirt with them, lifting it slowly.

He slid down until he was kneeling on the floor. He lifted my skirt over my straining cock. He took it in his hand and started stroking it slowly up and down as he looked at it fascinated. He licked his lips, clearly nervous. Oh god was he going to...? He took the head between his lips and ran his tongue around it. I let out a deep soul shaking moan.

Here's the thing. I never fantasized about having my cock sucked by a man. Women yes, but not a man. I know a lot of guys want to do that with girls like me, but for some reason the thought just never appealed to me before. Now, feeling it for the first time, wow!

I leaned back and closed my eyes, savoring the sensation as he took me in his mouth. So warm, so wet, so wonderful, I now knew what it felt like for him. He sucked it for a while and started to really get into it. My hips were gyrating and I was moaning like crazy. Then I felt his hand moving up my inner thigh, I spread my legs wider.

His fingers found my tight little hole and pressed against it. Then he wet them with his mouth and returned to pressing, this time pushing inside me.

"Mmmmmmm!" I cried out as he penetrated me.

Soon he was sucking me with his mouth and moving his fingers in and out of my ass.

"Oh Fuck! John" This was the first time I had ever called him by his given name.

"Mmmmhmmmm" I wasn't going to last long like this. I needed him to stop, I didn't want to cum yet.

"Oh gawd, John please" cried out urgently "you need to stop"

He kept doing it.

"Ohh John please" I cried "If you don't stop it's gonna happen"

"Oh god John please"

"Ahh fuck please, please"

That was it, I couldn't stop it. My body started to tremble with the effort of holding back. Then the sensations ripped through my defenses and my body started pulsing and trembling as I came deep in the warmth of his mouth. It was both incredible and disappointing at the same time, I am not sure why. The sensation left me both drained and hungry for more. He kept sucking until I was done and he swallowed before lifting up to kiss me, his finger pulling out and leaving me feeling empty. I could taste cum on his tongue.

If I was worried that cumming would cool my fire, I was totally off base. He was on me now, kissing me deeply, caressing my breasts and rubbing his cock on me. It was driving me wild. I wasn't hard, but I could tell I would be soon if this kept up. The important thing to me is I was every bit as turned on as I was a few minutes ago.

"Move up" he urged me. I scooted myself up the bed underneath him and he moved up with me. Again he was on top of me, laying between my legs kissing me with passion. I ground myself against him. His cock was working itself between my legs. Soon the head was pressing against my ass. "Oh god this is going to happen" I thought to myself as he pressed harder.

In my dreams he would just take me, thrusting hard and deep inside me. Reality is a lot more complicated. First off, I came so quick earlier that he only fingered me for probably less than a minute. Second, lubrication, or lack thereof was a problem. I was still a little wet from his saliva but his cock was completely dry.

It started to hurt and I stopped him. I reached for my purse, which I wasn't far away on the bed where I left it. I got out a little tube of lubrication. I reached between us and fingered myself for a few seconds, working it all around. Then I poured some more on my hands and stroked his cock, getting it all wet and slippery.

Then I pulled him back down on top of me and we resumed kissing. I wanted him in me now. I wanted to feel him move inside me. He wanted it too. We were both pretty impatient.

He tried as before but the head kept slipping off target. I reached between us and tried guiding him. He pressed forward and he started to open me up, but then he slipped out of my fingers again. This was getting frustrating.

"Sit up." I said matter of factly.

He did, looking a little confused and frustrated.

"This should be easier." I said, taking both of his pillows and placing them on the bed and I lay down on my stomach with them under my hips. This lifted my ass in the air. He hesitated for a second and then scooted up between my legs.

This time he could see what he was doing and use his hands too. He put the head of his cock against the tight ring of my ass. I could feel his hand pushing down on the head, guiding it in. I tried to relax. I looked at him over my shoulder and his expression was one of tense concentration.

Oh fuck! It didn't exactly hurt, but it was intense. I felt like I was being split in half. Practicing with a dildo was a lot different. I could control what was happening. He was a little thicker than my dildo and his weight on top of me all concentrated on his cock which was pushing past my resistance.

I couldn't help the sounds that were coming from my throat as I felt him entering me.

"Am I hurting you?" he asked with concern, "Should I stop?"

"nooo please keep going" I panted, pushing up with my ass a bit to encourage him.

"Oh god" he sounded surprised as his head slipped in at last.

"Oh fuck" he pushed deeper.

I was moaning incoherently. The feeling was incredible as I felt him fill me. Pain and pleasure mixed perfectly. Then he was all the way in and I felt his weight on my back. He held me and kissed my neck as we lay together hardly moving, just breathing heavily.

My body relaxed and accepted him after about a minute of lying together this way. It started to feel really good. I relished having him inside my body. I wanted to feel him moving. I pushed back a little, he pushed forward a little, small movements.

Small movements turned to bigger movements. His hips started thrusting in longer deeper strokes. Every time he pulled out I pushed my ass up, I wanted him back in me all the way. My hands had his comforter in a death grip as I realized we were fucking. He was really fucking me. There started to be little slapping sounds as his hips impacted my ass.

"Oh fuck" he started saying over and over"

"Oh fuck, oh fuck, oh fuck yes fuck!"

Then he was driving into me hard. His dirty talk was turning me on like crazy. Our moans turned to shouts of pure ecstasy as I felt his full weight driving into me. As almost an afterthought I felt that I was hard again and my cock was being driven into the pillows beneath me. It felt amazing once I realized it.

"I can't..." he panted.

"I can't stop it." he finally got out, his breath ragged.

"Cum in me." I begged.

"Yes!" he drove his cock deep

"Do it!"

"Yeah?"

"Yes fucking do it!!"

"You want it"

"Yes!!"

"Oh fuck yeah here it comes!"

OK so I like to talk dirty during sex apparently. It was really a big turn on. I guess I probably watch too much pornography; maybe I wasn't as sweet and innocent as I seemed.

He drove into me one more time, deep and hard. I felt his cock pulsing. I felt warmth spreading from my ass throughout my whole body. A completely new sensation and it was wonderful as his cock continued pulsing inside me.

It was a strange sensation as he lay on top of me spent. His cock was still somewhat hard and that warm sensation was all through me. I felt like I was floating on a cloud. My cock was raging hard pressed against the pillow and to be entirely honest I felt like it needed to cum more than I did. It wasn't hard to let go and just enjoy the feeling.

He started to soften after a bit and pulled out of me, leaving me feeling empty and fulfilled at the same time. I could definitely get used to this sex stuff. I felt like I was on top of the world.

He rolled over on his back and instantly I was snuggled up to him, my head on his shoulder, my leg draped across him, mewing contentedly.

"That was amazing" I said.

He felt my hard cock against his thigh and said "You didn't cum?"

"Not that way," I said, "but I felt something else entirely, better even."

I described the warm feeling as best I could.

"Interesting." he replied "So was I really good?"

"Mmmm yes," I sighed "absolutely wonderful."

We lay together that way for about fifteen minutes and I was starting to feel drowsy. Another new thing I learned about my body was that my erection would go away for a bit and then come back instantly if he moved even just a little.

His arm was draped around my shoulders and from time to time his hand would wander over and toy with my nipples. This also brought back my erection immediately. My hand had started out massaging his hairy chest, but it eventually wandered down his body and I was very gently massaging his balls and soft cock. I just couldn't get enough of touching him. It was also super nice that we had all the time in the world and didn't need to run off immediately like last time.

He was starting to get half hard again when he suggested that we take a shower. We held each other and kissed a bit as the warm water rolled off of us. I could feel myself falling for him. Everything about him was just so perfect. I could hear my Mom's voice warning me that I might feel this way and to guard my feelings. Objectively I knew this was true, but I relished the feeling anyway.

We washed each other's penises, together. His soapy hands slid along my cock and felt amazing. We pressed and rubbed them together and kissed. He also spent an unreasonable amount of time washing my boobs, not that I was complaining!

Something else happened to my emotions during all of this. A piece of the grand puzzle of life fell into place for me. This was good and right for me, like life made sense. I am not so shallow as to think this was all there was to life, or even all there was to my sexuality. I just know that it is one thing that I really liked a lot and that felt important. I know it sounds cliché, like he made me a woman, but it felt something like that.

We toweled each other off and headed back to the bed. I thought about changing into some cute lingerie I had brought, but decided I liked just being naked together for right now. We both had that warm, moist just out of the shower glow to our skins. I was also surprised to know that I felt very much comfortable with my cock around him. I didn't feel like I had to hide it like it didn't belong. That was nice.

We lay back down together in more or less the same position as before. Now he was consistently playing with my nipple, rolling it back and forth between his big soft fingertips, pinching just a little. It was driving me crazy. I was stroking his cock for him, it still wasn't fully recovered but it was getting there pretty quickly.

"That feels good." I said.

"I'm glad you like it." he responded but sounded kind of distant.

"What are we going to do?" he asked.

I put my mouth on his nipple and licked as I squeezed his cock in response. He groaned.

"As much as I like that answer," he replied dryly, "I meant about us?"

"What do you mean? I asked, genuinely curious now.

"Well I like you" he said "a lot."

I sighed and nuzzled into his shoulder. I liked this nonverbal communication style, but I still answered. "I like you too... a lot."

"What about school," he said, anxiety rising in his voice "and my job?"

"What about them?" I asked "You're worrying too much."

"I'll be a good little student during the week," I said "and I will promise to try my best not to make you feel conflicted."

"I guess..." he said, trailing off. Then "Ow!" as I sucked his nipple again but this time I bit him playfully.

"and" I continued, "you can fuck me on the weekends."

"You worry too much" I said, "you have a naked girl in your arms and all you can think about is work?"

Then I was on top of him, kissing him and he tried to tickle me, which totally worked. We frolicked like this for a bit until I felt his hard cock brush up against my ass. Then things got serious.

I ground my butt back against his cock. It felt good. I still got a little thrill of nervousness, but not as bad as earlier. My cock was hard as a rock lying on his belly. I rocked my hips back and forth and he groaned in response. I reached to the bedside table and grabbed my little bottle of lube.

I lubed my ass and his cock simultaneously. He was thrusting up impatiently, sliding between my ass cheeks. I put some lube on my cock too, because it felt good sliding against his belly. I sat upright on top of him, straddling him. I lifted my hips and guided the head of his cock to press against my tight little hole.

I held him in place as I worked my ass back and forth, the head of his cock keeping a constant pressure against my ass as it started to work its way inside me. I let out an involuntary "oooh" as the head popped past the tight ring of resistance. Once the head was in I pushed back with my hips more, feeling every millimeter of movement as I worked his cock deeper and deeper. It was much easier this time, maybe because we had already done it once, but I think it was because I felt more in control of what was happening.

OK so it still hurt a bit. This time from getting fucked earlier, but it wasn't bad at all and after a bit it felt so good. I just sat, straddled across his hips, his cock inside my body. I looked down at him and he was looking up at me. I started to gently rock my hips back and forth, relishing the feel of being penetrated.

Everything was so frantic before that I really didn't have much of a chance to take it all in. This time we were more relaxed. I rose up and down just a little, trying to move my hips on him in a seductive sort of way. I was gently moaning.