Our First Time 50

Semi-autobiographical.

It was almost like a dare as it slipped past my lips. " I want to watch you pleasure yourself." I watched his face closely to see how he would respond. At this point, his words meant nothing.

"Uh, sure. I can do that." He squirmed in his seat, looking like a boy who got caught looking at naughty magazines, instead of the self-assured businessman that he was. I could hear the hesitancy in his voice. I saw how his eyes didn't quite meet mine. I knew he wasn't ready for me. Not yet...

"You know, I was thinking." I toyed with the spoon in my tea. "You really aren't comfortable with this. Why don't we wait until you are ready? I mean, it really isn't a big thing." I smiled to myself, checking out the uncertainty that was making him a quivering mass. "When you are ready, let me know. I would love to see how you touched yourself."

Without him realizing what he was doing, I saw his hand slide under the Denny's table He was stroking his member under the table. I could tell by the glazed look that came over him. When he realized that I was watching, he moved a glass of ice water and held it to his shaft, praying that it would go down before we were ready to leave.

The sight of him aroused and confused excited me. It made my nipples start to tingle. I could feel my clitoris start to pulsate and throb against the vinyl of the booth. Slowly moving my hips back and forth, I was able to create such a lovely feeling that I could barely contain myself. "Hey. I will be right back, okay?" I slid out of the booth and headed for the bathroom.

Before the door closed behind me completely, I had my hand sliding down the front of my jeans. I slid down the cold tile, my eyes rolling to the back of my head. My orgasm was so intense, so quick, that I could barely breathe. Once my pants had turned into deep breathing, I headed back to the table.

He sat there, drinking his cocoa, whipped cream clinging to his moustache. With the finger that I had just thrust deep inside me, I wiped the whipped cream off and offered it to him to suck it off. He could see the challenge in my eye. When his tongue made contact with my finger, a shock went through me. My still vibrating sex clenched up with need. He meant to make it just a light lick, but I saw the moment that he realized that he was tasting me. His lips started to suckle my finger. As the electric need coursed through my body, I jerked my finger back with a shaky laugh.

"Hey, watch out there now." I tried to act as if I wasn't about to cum right there again with my finger in his mouth. "That felt so good that I need to go and take care of myself again now." I smiled as I said it but my nipples were starting to ache with need. I gently rubbed them against the wooden table, trying to alleviate the sweet pain.

"Did you really?" He stumbled over the words. "Did you really...get off in the bathroom?" He looked so shocked that I wasn't sure if he was going to make it to the register.

I reached for my coat and purse and headed for the register, motioning him to follow. When he finally was standing behind me, I slowly shook my head yes. After he paid the bill, he walked me to my car. I figured now was the time to let him off the hook. "Baby, I know you aren't ready to let me see you touch yourself and that is okay. Call me when you are ready. I will be waiting." I gave him a kiss on the lips, slightly sucking his bottom lip into my mouth.

I watched him get into his car before I drove away. Damn, I wish he was ready. I really wanted to feel his shaft against the back of my thr...

The ringing of the phone interrupted my thought process. It was him. "I am ready." The words that I was waiting to hear came out of his mouth. I was so surprised that it took me a second to process what he was saying. I thought that he was going to hold out until the next day at least. "Follow me," he said.

I turned my car around immediately to tail him. As we pulled up to his house, all I could think about was how I was not going to mess this up by pressuring him for sex before he was ready. I really did want to see him as he gave himself pleasure. Sex could come later.

When we reached his bedroom, we both were awkward. Me, because I didn't know what to do so that he wouldn't scare and not do it. And him, because he didn't know how to proceed. We watched a little TV, both trying to look at ease. Both failing miserably. Finally, I could wait no longer. "OK, Baby, go ahead and entertain me."

"You have to do it with me." He was stalling for time, I could tell. But, he had never met the likes of me. That wasn't going to buy him much time.

"Fine. How do you want me?" Touching myself worked just dandy for me, because I was ready to get off again. And, I knew watching him would make me want to cum.

"OK, but you have to come to unwrap what you want to see." His coy act was not deterring me a bit. Before he could get the sentence out fully, I was working on his belt and zipper. My mouth started to water being that closes to his member. But, I controlled myself....barely.

By the time we had both shed our bottoms and got comfortable on the bed, I was almost antsy with need. I sat at the top of the bed, nestled in the pillows. He laid across the bottom of the bed, facing my sex. I opened my legs up wide, rubbing my fingers down my slit, making sure to get my finger wet with my juices. I was so wet that I could feel my wetness on my thighs.

Hesitantly, he began to stroke himself. Up and down, with a little twist. Watching him and feeling the slick petals of my vulva made me want to taste him. I wondered how he would feel in my mouth, on my tongue, in the back of my throat, as I watched.

I tried very hard not to moan as my inner lips got more moist. I didn't want to startle him. I could tell that he was still not completely at ease. My fingers dipped inside me, making me grind my hips. At that very moment, I watched as his fingers gently fondled his balls. I could tell that he wanted to watch me. Unfortunately, he was too conscientious to watch me watch him. "Are you okay?" I asked. "Do you want to stop?"

He grimaced but replied, "I am oddly at ease with this. It is okay." I knew how he felt. The first time I masturbated for someone else, I felt so at ease that I didn't have the comfort level to cum quickly. To take the pressure off of him, I closed my eyes and concentrated on how lovely the feelings were. I took a nipple between my fingers and started to pinch and pull on it. The feeling was so pleasurable, that I couldn't help but moan. My hips started to gyrate back and forth, round and round, until I cried out in passion.

I could feel him watching me. It made me cum harder to know that he was watching me cum. Once the wave of pleasure had subsided, I gently resumed pleasing myself. I watched him, still stroking, so silent. But then, I felt his hand creeping up my thigh. Thank you! I was waiting for a sign that he really wanted me.

I continued my ministrations on myself as he got closer and closer to my sex. I could tell that his hand on his member had slowed down. But, since it was I he was now touching, I couldn't really complain. Before I knew it, his fingers were pushing up into me. Filling me up completely. I don't know if it was three fingers or five. All I know is that I wanted them in me as deeply as he could fit them. My hips started to rock in time with his thrusts. Before I knew it, I had flipped on my stomach so that he could have access to me. With my legs spread eagle on the bed, my sex was completely open to him. My bottom bounced wildly as he hit my spot over and over again. At that moment, I wanted him inside me so badly.

He had other plans for me, though. His lips started grazing my leg ever so slightly. With a lick and a nibble, he had made it up my thigh in no time. All I could think was yes, yes, please yes! Just when I thought he would make it to my core, he surprised me and nuzzled my back left cheek. The five-o'clock shadow scraped my skin, leaving a trail of very happy goose bumps in its wake. By the time his lips made it to my clit, I thought I would die. My body shook and I wanted to hold his head right there, yes baby, right there forever.

It seemed like hours but after only a few minutes, he repositioned me on my back and pulled me to the side of the bed. He knelt and place my thighs over his back and dove back in. The spasms racked my body as I rode his tongue and twisted my nipples to and fro. I came over and over again as he licked and sucked my clitoris and teased my spot with his wonderful fingers.

As great as this felt, nothing could have prepared me for him sliding inside me. His shaft filled me up and landed right on the G-spot. It was like his shaft was meant for me. One position melted into another as he corkscrewed in and out of my womanhood. I think we hit at least the first 25 positions in the Karma Sutra before he stopped and started to stroke himself again.

"What's wrong?" I asked. Whatever it was, I wanted to fix it so that he could come back inside me.

"I am about to come. I am trying to pace myself." He looked so sexy rubbing my juices into his member, that I had to suck it. I tasted myself and him together and it was like an afrodisiac. The more I tasted, the more I wanted him. When I started to suck with more force, he laid me back down and laid that pipe back into me. With my legs on his shoulders, I was completely open to however deep he wanted to go.

My hips were moving up under him frantically. "You want to make me cum, don't you?" he asked me.

"I am not trying to make you cum, baby. I just want you to fuck me with everything you've got." I don't know if it was the word or the intensity, but it turned on another level inside of him. The next thing I know, I am behind up, face down into the pillows as he fucks me hard and deep. It feels so good that I had to stop myself from crying. Yes, baby. Please yes. I need it like that. I thought I was screaming it to him, but the feeling was so intense that I could not form cohesive sentences. As my honey walls pulsed around him, he pulled out and came all over my back door. I reached back and rubbed him on my cheeks, trying to get the last bit of energy and cum left in him.

Covered in sweat and cum, we both fell to the bed, exhausted but satiated. I cannot wait to have him again. And again. And again.

Fin