First Time with a Shemale

University of California located in Santa Cruz, CA down the coast from San Francisco. A laid-back beach community where rich liberals coexist with bohemians, or at least that is how I remember it in 1984. The campus was way up the hill from the beach and surrounded by dense redwood forests and meadows with killer views of the ocean.

Walking to class was an adventure. For example, my political class was always from my dorm and the path cut through the woods. One day I saw a fox and another a snake. The walk, and the fact I was failing out of college, both motivated to attend class often and on-time.

On Friday nights, we would go to the Laguna Creek Beach with its big sign stating "No Vals." There were usually 30 people with guitars, cannabis and beer. We would light a big bon fire which would light up the beach and produce a lot of heat. It was a lot of fun and often I would fall asleep and wake up in the morning to surfers and nude sunbathers, usually in their 70's.

One Friday night, me and a few friends headed to Laguna with a few six packs and an eighth of weed. Sure, enough there were 25 or more people there getting a head start on the evening. Some were from UCSC and others probably not, but it did not matter.

It approached 10:30 and it was dark as the fire was smoldering. Across from me was this really hot looking girl. Although I was dating this Italian girl I met who at UCSC and worked parttime for NATO, it was not exclusive and I had a girlfriend back in Boston as well which was supposed to be exclusive. I was a busy man.

I approached her with two beers and offered one to Carmella.

"You look hot and thirsty. Ok, you look really hot! Maybe this will help with the thirsty part."

She accepted it and I sat down. Another victory.

"I am Carmella," as she extended her hand out.

"They call me Jerry," as I took her hand and kissed it.

The guys several yards away smiled as if to say, "I know what you guys will be up to!" I was hoping that they would turn out to be right.

Carmella could not have been any older than 22 and any taller than 5'4" and around 120 lbs. Her boobs were small and round and looked great. Her eyes matched her hair color-jet black. She was wearing a black, loose, sleeveless shirt that allowed me to get a glimpse of her boobs when she leaned forward, and tight black jeans and pink sneakers. She was quite the girl. Oh, and she must have been wearing "Paris," and she smelled great.

She said, "I work in a clothing store on Pacific, The Blue Horn. I live in Santa Cruz near the beach with two roommates. I love this beach, especially at night."

My turn.

"I am at Uncle Charlie's Summer Camp getting some credits so I can graduate. I go to school in Boston and this is a really cool place. Met a lot of great people, but no one as beautiful as you are."

I was locked and loaded. My heart was beating fast and my eyes were affixed on hers. I had seen a lot of women in Santa Cruz but there was something different about her. She stood out.

As we spoke, she would lightly touch my arm from time to time, and I would sneak a peek at her boobs, which she did not seem to mind. I was getting aroused and I could feel my cock swelling in anticipation.

My friends came over and said they were heading back. I said that I was staying! I turned to Carmella.

"If you want to hang out I can run you up to the campus later," Carmella offered.

"Wow," I thought, "She was committing herself."

My friends were acting suspiciously like the time they sold me a joint made out of Lipton tea but I did not give a fuck. Carmella was giving me signs that she would be interested in more than just hanging out. I picked up on this and moved closely to her mouth as she looked into my eyes and I looked into hers. I was very happy and was present in the moment.

She really was a good kisser and her tongue was powerful and probing. She was not shy nor was she submissive. In fact, she was the aggressor as she guided me down to the sand and got on top of me, as we continued to kiss. I was planning my next move, or maybe I did not have to because she was obviously in control.

The first surprise was that her roommates were not home. They had gone to San Francisco for the weekend. Carmella asked me if I would like to have a drink at her place. The other option was that she could take me to the dorm and I could masturbate in the shower. I chose option one.

It was a 10-minute drive along the coast and we arrived at downtown Santa Cruz. It was very quiet and not many cars. As she drove we enjoyed the solitude and held hands. She drove up the hill and pulled into her driveway. It was a small house, painted yellow with a small porch. We walked up the wooden stairs and she invited me to sit down next to her on the porch swing.

She put her arm around me and begin kissing me again. I felt overcame with puppy love. She then paused and lightly pushed me away as her right hand rested on my thigh.

"What was she going to do or say next?" I thought.

"I am a special kind of girl. Probably not like any other girl that you have ever gone out with."

I could feel my heart rate increase. My mind was racing and trying to anticipate what she would say next, but it did not come up with any answers. There was a pause which seemed like 5 minutes but was probable only 15 seconds.

She continued, "When I was born, I was not who I am today. Yes I was female but trapped in a male body. Do you understand what I am telling you?"

"Not really." I smiled.

As far as I was concerned, she could have been speaking to me in German.

I was starting to catch on but did not want to jump ahead so I let her continue.

"I was born with a boy's body but a girls heart, mind and soul. I am a woman, but not entirely."

"Not entirely?" I thought as I started to catch what she was trying to say.

Her German was started to sound a lot more like English to me.

Carmella could sense my confusion, and wanted me to understand, so we could move forward one way or another.

"I am transgender. I have augmented breasts-a boob job. I think that I have a girl's figure but I have not had the operation below my waist. I have a penis."

"Fuck! I have been kissing a guy. But she does not look, smell or talk like a guy. She was a better kisser than my girlfriend and had nicer boobs.

What the hell!" I thought.

I responded, "I have never been with a special girl or a guy."

"I thought you had picked up that I was Trans, but realized you hadn't, so before we went any further, I wanted to make sure you knew. Would you like that ride home now?" she asked.

Masturbate in the shower or have her suck my cock. I will opt for the latter.

Instead of answering her, I began kissing her aggressively as she wrapped her arms around me and squeeze the air out of my chest. For the first time, I looked at her crotch and could make out the outline of a head of an erect penis. It kind of looked hot; at least I knew she was into me.

The air was cool and the swing was moving back and forth as we made out. By now my hand was under her shirt and although I knew how those boobs got here, I did not care.

"Would you like to come inside?" she said.

I got off the swing and followed her to the living room.

"Drink? Vodka, Bourbon or Tequila." She offered.

"Tequila. Double."

As she began to hand me the glass I snatched it away and downed the Tequila as she downed her bourbon. She lit a cigarette as she offered one to me. We just sat there quietly smoking when she gently blew smoke in my face signaling there was more to cum.

I started thinking how I love when women taste like beer or booze and cigarettes. It is sexy in its own way.

She kneeled in front of me. Without any thought my legs parted and she unzipped my jeans and pulled them down to the floor. It was obvious that I was still turned on and she gently stroke my cock while it was still hidden by my underpants. It just kept getting harder and the anticipation of her sucking my cock was driving me crazy.

Finally she released my cock and removed my underwear. It sprung to attention. The tip was soaked with precum.

She wasted no time and licked the precum off my cock. I focused on not cumming and ruining the evening. But her tongue continued rubbing against the head of my cock as I worked harder not to shoot my load. It was a battle.

Finally she took my cock into her mouth and began giving me an intense blowjob. She knew what she was doing. Her checks were inverted as she sucked so hard as she slid my cock in and out of her mouth.

I knew that I couldn't last as I grabbed her head and shot three big loads into her mouth. Unlike many other women, who would gag and then spit it out, she savored it like fine wine and swallowed it like a champion.

All she could say was "Hmmm."

I was still hard. I knew in another 15-20 minutes I could cum again. But what about her? I was sure she wanted to cum.

My forefinger started to trace the head of her cock through her jeans and she just moaned. I guess she needed it just as bad as I did. The more I touched her the more she moaned.

By now my hand was stroking her cock through her jeans. Her expression said that she was close to cumming. I unzipped her jeans and her cock just popped out-she was not wearing underwear. Her cock was very large, larger than mine and it was wet with precum.

"Am I really going to do this?" I said silently.

I was.

I started stroking her cock as if it were mine and she was very hard.

"Am I doing this right?" I asked.

"Yes... harder. Faster."

I continued to stroke her cock and pretended that I was masturbating. By the sounds she was making, I knew that she was ready, so I got down on my knees and let the tip of her cock enter my mouth. As I licked her precum, I realized that it was much sweeter than I imagined. It tasted great like a 20 year old's cunt.

I started really sucking the head and was guiding my head back and forth until all of the sudden I felt my head being forced forward and backward, as her cock hit the back of my mouth again and again...

"Oh fuck I am cumming" she said as she shot her load into my mouth.

It was not as sweet as the precum and I spit it out on the floor. We both laughed.

She poured us each a drink.

"How was it?" she asked.

"Different. You have a nice cock and you give a great blowjob."

She seemed pleased with my response as she downed her drink. I downed mine as well. The tequila masked the taste of her cum.

"Would you like to spend the night?" she offered.

"You mean not go back to an empty bed? Sure!" and we laughed.

We sat in the living room with my arm around her and we talked and laughed until a 1:45 AM when we finished our last drink and extinguished the cigarette that we were sharing, and I followed her into the bedroom.

She went to the bathroom and I could hear the water running and the toilet flush. She came out wearing a slinking blue nightgown that barely reached her knees. I also noticed she was wearing panties that matched. She looked really hot and fuckable.

"Your turn. You can use my toothbrush and you're welcome to take a shower. There are clean towels folded on the shelves."

I went into the bathroom and decided to take a shower. The water was warm but not hot. It felt good and taking a shower without anyone else in the bathroom was a rarity on campus.

"They must have the thermostat on the water heater down pretty low." I thought as I finished my shower. Young people were always looking for ways to save money.

I dried off and entered the bedroom naked as the day that I was born. My cock was half hard and she took notice as I laid down next to her and we cuddled. It was after 2 AM and I was wide awake.

I reached over and started to feel her cock inside her panties as she smiled. I don't think sleep was in her vocabulary, at least not that night.

The more that I touched it the harder we both got hard. It was hot.

"Would you like to fuck me?" she asked with a big smile.

I had never had anal sex. I never thought that I would be with this kind of woman much less having anal sex with her. But the thought of fucking her was very exciting.

"Sure-I want to fuck you."

In her night stand she had a packet of lube and a condom. I did not want an STD that I could not cure, so the condom was a welcomed sight. She took off her panties and applied some lube to her asshole. She opened up the condom and put it around the head of my erect cock. She laid down and started to suck my cock and unroll the condom at the same time-she was very talented.

She applied some lube on the condom and I guess I was ready to fuck her. She looked some much like a woman that it was not going to be much of a problem for me to stay aroused and engaged.

"I am going to guess that you have never fucked a girl in the ass right?"

I just nodded yes.

"Here are some options: I can be on top and ride your cock up and down while we look in each other's eyes and you can play with me. We can do it doggie style. Or we can spoon with you as the big spoon and you can fuck me and we can kiss."

Doggy style never did anything for me. If she was on top, I would not have to do anything. I was tired so that sounded like a solid choice. But if we laid down, then we could kiss and she was the best at it. Kissing always made me so horny.

"What is it about kissing?" I thought.

"Do you have a preference?" I asked.

"It is your first time. You pick." She responded.

"Ok, I want to fuck you laying down so we can kiss and I can play with your great tits."

I could tell from the expression on her face that she liked both my choice and the reasons why, as we laid on the bed with me behind.

"Gently... it is an ass pussy and mine is tight." She said.

I grabbed my dick and got gunk on my hand which I wiped on the sheets. I started to take stabs at her ass unsuccessfully. I felt her hand over mine directing my dick right to her hole and I started to enter her.

It was really tight. As tight as a virgin pussy. She moaned as I went in deeper but ever so slowly. Finally, I was all the way in and my hand found her erect cock and it's precum soaked head.

My fore finger was getting wet and sticky from playing with the tip while my hips thrusted my cock in and out of her. Damn it felt good. And her moaning became softer as I pulled in and out of her ass.

I took my sticky forefinger in her mouth and she laughed out loud and said, "You are a naughty boy."

My thrusting got faster as I grabbed on to her tits and our mouths made lustful music together. I was definitely ready to cum.

I pulled out-maybe a little too quickly because she made a sound of discomfort. I turned her on her back and started to masturbate inches from her open mouth. She was such a willing participant and having her watch me masturbate was just too much excitement, and I shot my load missing her mouth and hitting her eye.

My girlfriend would have been mad. My wife would have been very madder. But Carmella laughed and said something about me not becoming a marksman.

She got up and went to the bathroom presumably to wash her face, her eye and hopefully brush her teeth.

"Another cigarette?" She asked?

"Yes." I responded.

She smoked Marlborough's. The original red pack, not the shitty Marlborough lights. Girls typically did not smoke Marlborough's, at least the girls that I knew.

We returned to the scene of the crime, the porch rocker. There, holding hands, we shared another cigarette. It was the best sex that I had ever had. And she was the most erotic and exciting woman that I had ever been with although technically she was only the fourth woman that I actually fucked. At least I think she was the fourth; did I miss anyone?

In the morning, around 9 AM, we got up and I offered to cook breakfast.

"I make a great omelet," I boasted.

She made coffee in one those hourglass coffee makes. It smelled great and I could not wait to have a cup.

I was in no rush to go to the dorm where I would surely get the third degree. Reflecting back on the events of the night, did the guys at the bonfire know she was trans? Undoubtedly they did. Did my friends know? How did they know and I didn't know?

After breakfast we decided to go back to Laguna beach, which was clothing optional. Carmella said that she always opted to leave her bottoms on. We both laughed. But I was free to go nude.

As we laid next to each other on towels, my mind drifted back to the events of the evening and I smiled. The series of events that resulted in my giving my first blowjob to a beautiful woman-shemale. I fell into a deep sleep while the sun warmed my body but she warmed my heart.

Would I ever see her again?