A Virgin at 20 Pt. 01

It was a frozen winter in Detroit, I was bundled against the wind and cold. The cold wind forced my face down, away from the wind. I am 39 and on the way to a meeting, today I am retiring, 29 years of modeling and taking life cautiously, has taken its toll.

I live quietly and modestly, I was never sure of when my next job would present itself, it made me frugal. My parents used my modeling income to pay for my tuition and setup a trust fund, so I would have a nest egg and I had the option of retirement at 40 years of age.

My parents guided my every step, they helped me make career and life decisions, they kept me grounded and hold tightly onto the reigns.

I could never live the, "night life," I had to protect my reputation and my source of income. Being a model was like living in a glass cage, it was interesting, educational, exhausting and frustrating.

I attended private schools and had a tutor when I traveled or had a long modeling assignment. My tutor kept me well ahead of the classes in school, she visited me at least once a week, making sure I was testing well ahead of my classmates.

Some subjects like, race was not a word, not a topic, not anything I was involved in, not anything I would have an opinion on. I knew models that were not white, but models were beautiful, objects that I enjoyed and had to deal with.

Dressing rooms did not always have a gender, boys and girls dressed together and shared makeup.

Some things were never discussed, drugs were always negative, liquor was a drug. I learned how to enjoy life sober.

Everyone thought I was a genius, my tutor would scan fashion magazines with me, we discussed fashion, people and life in general. I was matured well beyond my years, even though I was naïve and sheltered.

I never had been on a date, the whole time I attended high school. My first date didn't happen until I was 19.

I had friends but was never in a circle of friends. My one close male friend, Dan was two years my senior and a model. We helped each other and socialized, movies, meals events and we traveled together.

One of our trips I saw him with his shirt off, he was well defined. He trained and maintained a strict diet. Dan was another model. He helped me with maintain my weight and sometimes we exercised together. I was surprised that my parents would allow us to be alone.

I enjoyed being with him, he was a close friend and never expected anything in return. He was beautiful, but manly. One night I walked into the bathroom and he had just walked out of the shower, I surprised him, he just smiled and kept on drying.

I walked over to him and put my hand on his chest, "turn around," I said. His butt was shapelier than mine. I put my hands on his waist and slid one hand over his cheek and squeezed. He turned around, "my butt is tighter than yours," he said, and the smiled.

My hand was even with his penis, it brushed against my hand when he turned. I opened my hand and wrapped it around his flaccid penis. I squeezed, it was very warm to touch. I stared down at the thin hand wrapped around the sliver of flesh.

This was my first encounter with a live penis, I had seen porn on the internet, I never saw a soft one. Dan looked down at my hand, I squeezed and started tugging. After a few minutes, I looked up, Dan was smiling. "What are you trying to do?" asked Dan, I thought it would get bigger. Dan smiled, "have you ever seen me with a girl, other than you?"

I just looked up, "I guess I'm not your type."

"You're perfect as a friend, and I love you like a sister." I wrapped my arms around his neck and kissed him on the lips, soft and long. I used my tongue, he kissed me back. He lifted his head, "thank you," I said.

"My first kiss," it felt wonderful, gentle and slow, I was flushed. I looked down at his still soft penis. It all started to fall in place, may parents let me spend time and travel with Dan, I guess they knew he was attracted to guys, so I was safe with him.

After that, we grew even closer, we slept in the same bed, sometimes we showered together. He was comforting, and I slept better in his bed.

I asked him questions about sex and how he made love to another man. He explained everything to me, I told him about my girl parts and even masturbated for him.

I made him smell my hand after I masturbated, he enjoyed it. I asked him if all guys like to have their penis's sucked, he said, "definitely".

I talked to Dan every day, we talked about everything, jobs, training, our love life, mostly his. I told Dan he was a whore, he hooked up a lot. Dan explained it was just sex, he didn't have any feelings for any of his partners, it was better than playing with yourself.

Next time we were in bed, I told him I was jealous, I have never had an orgasm with anyone but myself, Dan laughed so hard he had tears in his eyes. The next time we slept together I reached down and started fingering his penis. I did everything to it, squeezed it, rolled it, tugged at it and played with his balls.

I asked Dan if he had a big one, I think I'm a little bigger than most of the ones I've see.

"I wish I could see you hard." Dan laughed and said," I doubt sisters talk that way to their brothers."

"Shut up," I told him, "I'm always horny, I think you should help me out." Dan was facing me, he wrapped his arm around me and kissed me, Dan was a great kisser, gentle and loving. His tongue was against mine, it was a great kiss.

I spread my legs, "get on top of me." He rolled between my legs. I wrapped them around him and started grinding against his pelvic bone. This was erotic, Dan wrapped his arms around my waste and was grinding against me, "keep going," I asked.

I started to cum, I moaned into his mouth over and over, I grunted and had a great orgasm. He ground against me for a minute or so. I pushed him off me, I bent over and kissed his chest and moved my head down towards his crotch.

Dan let me go, I reached for his soft white cock, I guided to my mouth. It smelled like my crotch.

I sucked it in, my lips wrapped around it. Soon my lips were down to the base and I was sucking and tonguing his cock. I worked on it until my mouth was sore. I lifted my mouth off his noodle, I turned my head and looked up at him, "What else can I try?"

"That felt good, I think someday you give some guy a great blow job." I was horny again, "I like sucking you, it makes me horny."

"Don't you think you had enough?" asked Dan. "No, I want you to finger me." Dan said, "you are demanding," and started kissing me. His hand reached for my breast, gently he squeezed.

I was hoping he wasn't teasing me. His hand moved down to my crotch, his middle finger separated my lips, they were slippery, his finger tip pushed into me.

I tilted my hips up, his palm covered my crotch and his finger was slowly pushing into me.

"Dan, that feels good," he pressed his hand harder against my crotch and let his finger slide past my lips. I wrapped my arms around his neck, opened my legs and let him finger me.

He played with my pussy, I was groaning in his mouth and grinding against his hand. I came, hard and very slowly. I reached down and covered his hand with mine, I ground my crotch against his hand.

Dan stared down at me, I relaxed, "don't move your hand," I may want more.

He laughed, "don't be a slut." I pushed him off of me and rolled on top of him, wrapped my arms around his neck, and I kissed him.

Dan, "I think I love you, I never want to let you go." Dan smiled, "thank you, you are my dearest friend, we will always be close." I felt like sucking him, I started moving down his chest and torso, when my mouth reached his pubic fuzz, I looked up.

"I wanna suck your dick." Dan put his hands around my head and guided my mouth to his noodle. I sucked it in, I went all the ways down.

Dan said, "Stick your tongue out and lick my sack."

I obeyed, my long tongue reached half way down his balls, I licked and sucked. I pulled my head half off his cock. He moved his hips and started fucking my mouth. He held my head tight and fucked my mouth hard. I let him use my mouth.

Dan never got hard, he pulled my head off his noodle. He spread his legs, lifted his hips and pushed my mouth towards his ass hole. "Lick my ass."

Dan moved my mouth down, I licked his ass. I moved my head and pushed my tongue into his crinkled ass hole. I stuck my tongue out and pushed it into his ass. I was an aggressive ass licker. I spread his cheeks with my hands, he pressed my mouth hard against the crack in his ass. His ass cheeks were rock hard.

My tongue started aching, I slid my finger into his ass, as deep as I could force it. I looked up and could see his face. I also noticed his penis was thicker and half hard. I reached with my other hand and grabbed it, I gently squeezed.

Dan was hard, he had a big cock, I moved my mouth towards it. Dan's hand reached for my head, grabbed my hair and guided my mouth to his cock. He shoved my face down onto to his cock, I kept my finger moving in and out of his ass.

My head was moving faster, my lips were pounding against his pubic bone, I sucked his cock. Dan was fucking my mouth, his cock was hitting the back of my mouth and sliding down my throat. My finger was still sliding in and out of his ass.

Dan was not being the gentle lover I knew, both his hands were holding onto my head and his cock was fucking my mouth. I couldn't think about anything but my finger in has ass and the pounding my mouth was getting.

I kept sucking and using my tongue, I noticed a change, Dan slowed down and pushed my mouth against his crotch. My throat filled with cum, I had to stop sucking, I was trying to swallow but the head of his cock was in my throat.

My eyes watered and the cock in my throat started shrinking, I started to suck again. I lifted my head up, I choked and Dan's cum ran out of my nose and mouth. My mouth was directly over his soft cock, cum and spit was running out of my mouth and onto the softening cock.

My head dropped, and my face was laying in the cum and drool from my throat. I finally lifted my head and looked up, Dan was smiling. "Am I a good cock sucker?"

Dan couldn't answer, he was recovering from his first blow job from a girl. My face was a mess, covered in cum, my lips swollen and my eyes almost closed.

I wanted to put his cock back in my mouth, but Dan kept my mouth away from his soft noodle.

Dan sat up, "we need a shower," he got out of bed and walked to the bathroom, I followed.

We showered and walked back to bed, we lay in each others arms and fell asleep. We slept in, nothing to do but enjoy the glow.

Life continued, work, school and my relationship with Dan.

One night Dan was coming back from a long modeling job, I did missed him. I picked him up from the airport, I hugged and squeezed him tight.

We arrived at Dans' place, he was tired, I made a salad, we ate and watched TV on the couch. I stared at Dan, poked him with my toe. "Can I do anything for you?" He smiled, I'm exhausted, "Can I sleep over?" I asked.

Dan smiled, "of course, maybe you'll pamper me." I smiled.

I washed up, stripped down and jumped into bed. Dan brushed his teeth, he would never neglect his teeth, his smile was too important. I kissed him, I lingered and enjoyed his taste. I rubbed his back, then straddled his waist and massaged his shoulders, neck and lower towards his ass cheeks.

When my hands started getting sore, I leaned over kissed his back. My kisses trailed down his back, my face ended between his butt cheeks, my tongue licked his ass. It was wet, oozing and tasted funny. "why is it funky?" I slept with a friend last night. This was a first, I was tasting another man's cum, I pushed my tongue in his ass and started sucking, I could taste it.

I think Dan did it just to see how I would react, I loved Dan but I wasn't jealous.

The next day we were off, Dan had a meeting with a friend, a female friend. He asked me if I wanted to tag along, it was about work. We went to her office, small and neat, she was Dan's banking advisor. Lana was tiny, medium built, maybe a gymnast at one time, very smart.

They talked for a while, they discussed the future and how to beat inflation. Lana kept me in the conversation and asked me if I had questions. It was very informative, I had many of these types of meeting but never was able to contribute or ask questions.

Dan wanted to have lunch, Lana tagged along, she knew about modeling and public life. I learned that she was a gymnast and managed many the finances of many models and athletes. I was drawn to her, her confidence, knowledge and her attitude, she seemed to know when she was right.

Dan had to leave for another meeting, Lana said she could drop me off, so we stayed and chatted. She was very open, I told her how naïve I was about money and finances, my parents always directed me. I knew they were busy and maybe it was time I paid attention to my own finances. Lana said, we can talk about that some other time, we talked about Dan, his life style and how smart he was. I didn't want to discuss my relationship with Dan, so we talked about her.

Lana was compact, we sat close, so we could talk without raising our voices. She squeezed my hand a few times, she was strong, I was drawn to her. On the way out, we stopped at the ladies room, I stared in the mirror, I looked like I was 10" taller than her.

Lana dropped me off, we exchanged phone numbers, she said she was open all week, we made a diner date.

She dropped me off at my parents' house, I told them about Lana and how Dan introduced me to her, they were pleased. They were glad I started taking an interest in my financial future.

Lana called me that night and we arranged to have coffee in the morning, I would pick her up.

I woke up early and spent time dressing, long pants, heels and a tight blouse, I wanted to look tall and lanky. I knocked on her door, she opened it and stepped back, and looked me up and down.

"Wow, where are you taking me for coffee?"

I smiled, "anywhere you want." We had a great time, I stared at her, she had a great body. She was short, but I know she would be pushy and in charge. I sat close to her, it excited me.

We finished our coffee, we both had coffee breath, I was glad. I walked her to the door, "can I use your bathroom?"

She grabbed my hand and pulled me in, it was awkward, she circled my waste with her arms. She looked up and I looked down, I bent to kiss her, it was a real kiss. I was the girl, she took charge and we ended upon the couch.

I let her have her way, I sat down, she straddled me, her mouth and hands were all over me.

Lana looked at me, "have you ever been kissed by a girl?"

"No, never, but I'm enjoying myself." Lana unbuttoned my blouse, while she looked at my face, she kissed me while she unhooked my bra. My nipples were hard, she squeezed and pinched, they hurt but felt good.

Lana stood up and started undressing, when she rolled her pants down I was expecting to see a cock between her legs.

Her thighs were thick and muscled, her body was toned and turned me on. She stripped down, she was naked. She reached for my hands and placed them on her ass cheeks, squeeze them, her ass cheeks were tight.

One of her hands went to the back of my head and pulled it to the bush between her legs, she pressed my lips against her bush and tilted her hips up. My lips were against her pussy lips, I kissed her and smelled her mushy crotch.

After a few kisses she pulled me to my feet and finished stripping me, my pants and underwear were gone. We were naked and breathing hard, I could still smell her musky scent on my lips.

Lana turned and laid back on the couch, she pulled me on top of her. We kissed, she spread her legs, I remember when Dan played with me. It was easy, I moved my hand down between her legs and slid my finger between her pussy lips.

Her mound was puffy, when my finger parted her lips, there was no resistance. My finger pushed in deep, I could feel how wet she was. We kissed and I fingered her, she was aroused but never had an orgasm.

Lana said, "kiss me," when I bent to kiss her she pushed my head down, I ended up with my mouth kissing her pubic area. She pushed my mouth further and tilted her hips. My mouth covered her crotch, my tongue slipped between her lips. I felt like a slut, I was enjoying myself.

Lana's crotch was sweaty, it was different, not unenjoyable. I used my thumb to rub her clit and slid my tongue into her. I lifted my head to see her face, I think I was watching her orgasm.

I let her finish, I moved up and was face to face with her. I know my face was a mess, she pulled me down for a kiss. "Thank you for eating my pussy," said Lana. I was quiet, my first oral on a girl. I lay beside her, she was still breathing hard.

I started talking, "I'm a virgin."

Lana said, "I couldn't tell, you eat pussy like you were meant to." I laughed. "No, my pussy is virgin, nothing else." Lana was confused. I started explaining my sex life and my sexual status.

I think Lana was still confused but accepted what I was saying. Her hand moved to my breast and started massaging me.

I asked Lana, "what can we do now?"

Lana got off the couch, grabbed my hand and led me to the bedroom, she pulled down the covers and pointed to the bed. She went to the night table, opened the drawer. She pulled out a couple of plastic penises, they had veins and big cock heads, one was small, one was larger.

I looked at her, "why do U need two?"

Lana answered, "I usually use only one, but let me see if you can take both.

I smiled and spread my legs. Lana knelt between them and put the tip of the small dildo against my pussy lips. I felt it hit my hymen, it didn't hurt, I reached down and spread my lips as far as possible.

Lana leaned down and covered my clit with her mouth, she started licking, I started grinding my hips. I felt the head of the dildo push into me, there was a sharp pain.

I put my hand on the back of her head and pulled her mouth tight against my mound. It felt good, the dildo hurt, but I was getting used to it. I started to cum. Lana kept licking me and fucking me with the dildo.

I had to push Lana up, she looked down and smiled. The dildo was still in me, I lay there breathing hard. Lana laid next to me and put her hand on my stomach, she moved it towards my mound.

Her hand stopped at the dildo and pushed it farther in. I smiled, "I hope it's not too big," she started giving it short strokes, I was tight. It's too tight, Lana pulled it out, she looked at the blood on it. "I'm not a virgin anymore."

Lana started talking, "I didn't think that you would like girls."

I smiled and said, "I don't, just you, you feel good and taste good." Lana leaned over and kissed me, I told her that we have to keep it quiet, I can't afford to lose any jobs. She smiled.