My First Time (Part I)

I was sitting in a cafe near the apartment I shared with Tom.
It was October, and the fall winds made cold enough for me to wrap up in a sweater and a pair of old but very snug jeans. It was nice and warm inside the cafe so I unbuttoned my sweater enough to reveal my cleavage.

I sat there sipping my tea and read a Cosmo. I had my legs pressed together and did my Kegel exercises, clenching and unclenching my vagina. A busboy, in his late teens, came by to clear a nearby table.
I looked up enough to see him staring at my bosom. He was really cute, in a trailer trash kind of way, so I didn't mind. I thumbed through the Cosmo and paused at an article about 'first times'. That made me smile because I was about the same age as the busboy when I was deflowered.

It was late in March my senior year in high school and lot of my girlfriends had lost their cherries to their boyfriends, most of whom were going to a Catholic school across town.
My own school, this was in New Orleans, by the way, was a Catholic school too. I lived with my mom in a small house in Bayou Saint John, the same neighborhood as the school. Mom didn't come home till late each night, so when I got back from school I had to go inside turn on the air conditioner and wait for the house to become bearably cool enough to stay inside.

It was hot outside, as usual, but a nice breeze was blowing and I went to go sit on the bench-swing outside. I still had on my school uniform, a short pleated skirt and a white blouse, and, taking off my high-tops, rested length-wise on the bench. Since we were on a side street, not many people came by, so I hitched up my skirt high enough to let the breeze circulate between my thighs.

I used my left leg to push the swing back and forth. It was so nice I started to feel drowsy. I wanted to touch myself, too. I slipped a hand under the elastic of my pink panties and caressed my clit for a while. Feeling a little daring I unbuttoned my blouse down to my belly button, and fell asleep there. I don't know how long I was there, but I did feel the cold blast from the AC. There was shuffling around on the steps leading to my front door and I cracked an eye open and there was the postman, a muscular and really friendly cutie, who liked to say hello to me.

He was staring at my crotch. The wind, or something, had blown the skirt up to my hips and left me exposed, except for the pink cotton stuffed in my crack. My heart raced, for a second I wanted to scream and run inside, but I was also curious too, as to what he might do. I was also afraid to 'wake-upâ because the situation might get out of hand. I could see his pants bulging at the crotch.

Maybe, I thought, he would just go away. And then the Devil, made me, as Sister Lucille liked to say, made me naughty. 'Are you going to put that in my box?' I asked. He cracked a smile, and looked at me, and then at the packet of mail in his hands. 'Hey, Kim, what's up?' He came over to me his hand holding the mail to me. I pushed the skirt back down and pressed my hand between my legs.
Groggily, I smiled at him and took the mail. I leaned over to flip through the mail, nothing but bills. I remembered that my blouse was open, and my breasts cupped in my bra, swung out a little, like little pale white pyramids.

Brian, the postman, was watching me. 'Anything for you?' He asked politely, lingering. I nodded my head, no. I looked up at him, his face was bursting with interest.
'Are you thirsty?' I asked.
'Yeah, I'm not supposed to, but I could really use a drink.
' We went inside. It was freezing cold. I shut off the AC, and opened the windows. Brian sat down on the couch. It was four oâclock.
Mom wouldn't be home till after 6. I got him a beer and poured a some of my mom's Southern Comfort, mixed it with some water and sat down next to him.

My heart was thumping like mad, I thought the drink would slow my nerves. I had buttoned up while I was in the kitchen, especially since the chill had made my nipples harden. I wondered what my friends would think of me. Karen would think I was brave, but she was 6 months pregnant, at 17, so she wouldn't be a good measuring stick.
He looked at me curiously. He had broad shoulders, and short dark hair. He liked working out, that was obvious. His eyes were blue. We talked for a while. . He was 24 or something like that.
He had been in the Marines, saw action in the Gulf War, and got a job with the mail after coming home. He said he saw me walking home sometimes from school.
He asked me what year I was in. I said I was a senior. He seemed interested. I'll be 18 in a couple of weeks, I told him. It was a little bit of a lie. He seemed even more interested.

'Where do you and your wife live?' I asked. My boldness trying to overcome my fear.
'I'm not married, don't even have a girlfriend.' a little bit of lie I later learned.
'Why not?'
'Just haven't met the right girl.'
'Oh.'
'How about you?'
'Nobody.'

We just smiled at each other. He finished his beer. 'Can I use your bathroom?' He asked. I led him to it. He didn't close the door all the way, and when I heard creak open a little bit I crept back into the hallway and looked in the crack in the door. Brian had a big smile on his lips and stood with a huge cock in his hand, peeing into the bowl.

It was a beautiful organ, so red, so long. He looked up and I ran back to the living room. I wasn't sure if he saw my face in the mirror. He flushed and came out. He smiled at me, CAUGHT! I thought.
'Well, I got to go,' he said, heading toward the door. I happened to be in the way.
'Well, don't be a stranger,' I said. He could have kept going straight to the door, but instead changed direction and collided with me.
I looked, surprise painting my face in rouge. He kissed me on the mouth and ran his hands up and down my ass. I stood on tippy toes to get closer to him and that encouraged him even more, moving my panties aside to feel my sopping wet labia. I pushed his hand away.

'Can I see you again?' He asked.
'When you bring the mail, tomorrow.' Mom, came and went again at 7. She told me she was going to do rounds (she's a nurse) but she packed her night bag like she was going to visit stay by her boyfriend's.
I invited Karen, who, like I mentioned before, was pregnant at the time, over to eat.
We ordered pizza and I told her about my day. She was all excited for me. She wanted me to go on the pill for him, and let him have me on my birthday.

That wasn't going to quite work, mom would be around and so on. So we decided that I would, if he turned out to be a really nice guy, let him do it to me when my body was ready for him. I stayed out sickâ the next day and went to Planned Parenthood with Karen in tow.

After an exam they gave me the pills. In just a couple of weeks, I could do it with him. It took a few days. Brian delivered in the mornings and I never saw him. Then one day there was a postcard addressed to me, with a phone number on the back.
'Call me, please, Brian.' I talked to Karen about that night and she insisted that I call him. A few days passed, and I finally got up the nerve to call him in the evening. Brian was really happy that I called. He asked for my number and we talked about all kinds of stuff for an hour or so, before mom made me get off the phone. We went out just about every other day. I set it so Karen would call and invite me over to 'study'. But really Brian would take me out to a restaurant and generally took me out on the town.

He would always dress really nicely, and looked so handsome in his dinner jacket and tie. I wore a dress whenever mom wasn't around to see me out the door, and a light blue eye shadow that Karen said looked really good on me. Sometimes he would invite over to my house and cook me dinner. We would watch a movie (usually some boring action film) and he would serve me wine. He had an apartment that shared a courtyard and a swimming pool in the center. There were four other apartments in the building, and Brian seemed to be friendly with all the neighbors who would all come out and say, 'hi'.

I got to really like wine and I often got drunk at Brian's place. After he sobered up he would drive me home. As the time drew near I responded to his touches (he had been getting friendlier all the time) more and more and we made out in his car. I let him kiss me all over.
On the Monday night before the big testâ I let him take my bra off (I wear a 34B) and he massaged my breasts.
He kissed each nipple, and sucked them too. I had never let anyone do that to me before and I got completely carried away.

He had a Honda Civic so it was easy to jump out of my seat and into his lap. I was wearing a knee length skirt with my blouse and I hiked it up when I sat in his lap. He lowered his seat and I straddled his hips. He always had a funny crease in his pants where it seemed like he might have a huge hard-on. I was dying to check it out. I threw my head back as he sucked away at my nipples.

He was gentle the way he cradled my breast with his hand that I didn't mind the progress of his hand down the back of my panties. He rubbed my ass and I pressed myself against him. The bulge in his pants was his dick and I eagerly pressed myself against him. He started to kiss my neck and sucked on my earlobes.
I let his tongue penetrate my mouth and got even more excited as his little muscle darted in and out of me. I started to gyrate on his hips, pressing my clit against his belt buckle. First hard and then softly, and then hard again, my cheeks burnt bright red as I came on top of him.

'unnnnnnnnnnnnnnnnnnnnnnnnnnnnnnnnnn' I started to yelp.
The contractions rippling through my abdomen started to subside and I unbuttoned Brian's shirt. He was so muscular, his chest so hard, compared to the pillowy softness of my body. I traced the shape of his abdomen and he reached under my ass and touched my labia.
I nearly jumped when he did that, and his hands fell to his sides, letting me take control. I unbuttoned his pants and stared at his organ.

It was huge and thick. The head reached to his belly button, and it was wet on top. 'What's that wet stuff?' I asked him. He seemed groggy and said 'it's precome. It's supposed to wet your pussy when I.....' His body rattled with pleasure when I took his cock in hand and rubbed it on the head.
I tasted it. It was warm and sticky, and it's taste, 100% man, I guess.

I slipped a finger between my labia and lathered his dick in my pussy juices.
'Isn't that wet enough?' I asked.
He was took excited to talk.
I did it again, stroking his dick. Brian's eyes rolled back and his hands clenched my ass cheeks.
Then his dick started to rattle and the little red cap on top started to spurt little globs of steaming white come all over the place. On my hand, and then on himself and my chest.

The smell reminded me of the taste from his dick. Brian seemed half asleep when his dick, shrinking now, stopped his little explosion.
His yelling tapered off into a sigh. I tasted the come on my hand. It was weird too. We kissed for the longest time and then I got myself together.

We agreed to meet again on Friday night and I got out of his car. The lights were out, mom was at the hospital doing her rounds, and I called to tell Karen all about what had happened. Friday came. Classes seem to go on forever. Mom would be away that weekend with her boyfriend so it didn't matter if I didn't come home that night. Brian seemed to sense that something big was going to happen. He called on Thursday and invited me to have dinner with him at Louis XIV, a fancy restaurant in the French Quarter.

When I got home I called Karen to see how she was doing. She was getting into her third trimester and was going to the doctor a lot, but she was still really into my first time. I was so nervous I could barely eat anything all day, but Karen insisted that I eat something. If I got too drunk I might pass out. Karen drove over to help me prepare. She had taken one of her boyfriend's pornos with her and we watched together in the late afternoon. I don't remember what the video was about (aren't they all the same anyway?), but I do remember trying to laugh with Karen. But really I was a little sick to my stomach. Karen and I sat together, holding hands.
I remember there was one scene where the man was really loving with the woman.
'I hope Brian is like that with me,' I said.
Karen leaned over and kissed me. I looked at her, astounded. Karen? I said, half smiling, enjoying it despite myself.
Karen seemed unsure of herself. She was so pretty, a brunette (I am blonde), with sparkling blue eyes. We were still holding hands, I guess that encouraged her.

'Come on girl, let's give you a bath.' She led me by the hand to the bathroom and watched me undress.
We'd been naked in front of each other before, of course, but this was different, more tender.

She bathed me with the most delicate touch, massaging me with different soaps and washed me down afterwards. She dried me off and ordered me to my bedroom. She painted my nails and toenails. She even picked out what I would wear. A short pleated black skirt and matching blouse. I put on a silver chain around my neck. Mascara and lipstick followed, and then some perfume.
I wanted to put a lot on, but Karen wouldn't let me. 'There,' when she was done fixing me up, 'you are so beautiful.' An hour passed. Karen waited till Brian showed up to drive me over to his place. He was wearing a dark suit and was extremely handsome that night... 'Miss....miss, do you want something to go?'

Woken from my daydreaming, I saw that same busboy standing over me.

It was getting late and I guessed they were closing soon. So I will finish this journal some other time...


My First Time (part II)

Karen went to take my Mom's leather jacket out of the closet. When she got back, I could already hear Brian's car pulling up to the curb outside. A chill ran down my body. Karen looked me over: my hair was done in a bob, with a rainbow barrette. I also had silver earrings and a necklace.
I was wearing a black tanktop with strings crisscrossing my bare back. I had on a short black skirt and pantyhose. I was (still am!) 34B-24-33 and stand 5â4, just so you know. Karen went to peak through the blinds.

'Oh my God, Kim, he's so cute!' She had seen him before, of course, but not dressed to kill like he was that night, in his dark suit and playful crawfish tie. He was getting out of the car and headed to the front porch.
Karen waved to me to go into my room. When the doorbell rang, she answered it, and after talking with him for a second, came to get me. I got off my bed and went to greet him. He pulled some flowers out from behind his back and presented them to me. They were so beautiful.

They also smelled so lovely, I blushed and kissed him on the mouth, the first time I had done that at the start of an evening. At the time I guess I believe that I wanted him to know what was going to happen that night, but looking back on it I figure I also wanted Karen to know that I was a big girl. At dinner we talked and held hands.
I kept on drifting back to earlier that day, with Karen. That kiss, the loving way she bathed me. Her advice that, if I was too scared, I could say 'no' and maybe give him a blow or a hand job.
I kind of laughed it off at the time. When towards the end of dinner he gave me a little gold bracelet with a little heart on it as a gift I felt sure that I was going to give him the gift of my maidenhood that night.
I leaned over to kiss him and let his hand drop to my legs, using them to rub his fingers against my pantyhose.

At his place we got even cozier. I straddled his hips, facing him. We kissed deeply. He unbuttoned his shirt and took off my top. His hands crawled up my legs.
He helped me out of my hose and sat me down on his hips. Breathing heavily, I unzipped his pants.
His organ was huge, engorged with blood, it looked like a red cucumber. I ran my hand up its shaft.
He trembled.
I admit I was getting scared, especially when he pushed back my skirt to stare at my slit.

His dick was just an inch away from my opening. I began to rub his dick, thinking if he came I wouldnât have to face my fears, but he got more excited. Picking me up he carried me across the threshold of his bedroom. It was dark in there, except for the light shining from the bathroom. He took off my skirt and I lay on his bed, naked.
He took off the rest of his clothes. Instinctively, I covered my breasts and watched his tightly coiled body emerge from its cotton shell. I was excited and scared, the moisture from my vagina coating my inner thighs as I pressed them together.

He came over and lay by my side. He put his hand on my breasts and felt my heartbeat, flying at a maniacal pace. 'You ready to do this?' He asked me, leaning over to kiss me. I nodded yes, lying.
He parted my legs and placed himself in between them. He stopped, I guess thinking about a condom. I said, 'no, I want you as you are.
' The soft head of his dick nestled into the folds of my labia. It tickled a little bit. I felt light headed, ready to laugh at any minute. Drunk too, I giggled. Then he began his descent into my body. He touched my hymen.

He kissed me again, and I braced myself by grabbing hold of his ass, my nails digging into his flesh. He pushed and I gasped. It hurt, of course, and I nearly told him to stop as he kept on pushing in. It was a strange filling sensation where I had never felt empty before. He began to slide in and out. The initial pain passed and his invasions became more welcome. 'You are so beautful,â he said and sucked a nipple. They were both erect and I felt a thrill whenever he would push his hairy chest against them. There was a smacking noise coming from down there. I looked up at him and he was deeply engrossed in his own pleasure. I was so happy to be giving it to him that I began to moan.

Karen had told me that faking an orgasm not only helps the man come but he enjoys it even more. So I pressed my pelvis against his and started to moan even louder. 'Come in me,' Karen said, speaking through me. Brian started to shiver and then pressed into me as far as his cock would go. I could have fainted from it, but his mouth dropped open and I could just barely feel this pulsing sensation coming from within my body.
He began to cry out, 'I'm commmmmmmming....'
I thought the whole neighborhood would hear. I made my legs go stiff, just like they do when I come for real, taking them from around his hips and laying them flat on the bed. I arched my back as much as I could on his soft bed and felt the pulsing sensation in me get stronger before it suddenly stopped.

Brian collapsed on top of me, his head beaded in sweat. We kissed. He lay inside me for a few minutes and then pulled out. We lay next to each other kissing and cooing in each other's ears.
His dick was shriveled up now, but his come was seeping out of me. I went and sat on the toilet, cleaning out his come. There was blood on the tissue and lots of sperm too. I fingered my clit, and came quietly.

His goop was all over my bottom so I ran a bath. I sat in the tub and nearly shrieked when the hot water touched my sore spot, seemingly penetrating me as well. Laying in the tub I felt like I was being fucked by a hot water knife. I finished washing and crawled into bed. Brian was mostly asleep. I lay on the mattress next to his slumbering body.
The wetness from our sex still covered the sheets so I cuddled up to Brian.
Soon I was asleep too.