Shirt of a Virgin Ch. 01

Story Info
Lucky charm gets man laid - or does it?
1.7k words
3.82
15.7k
1
Share this Story

Font Size

Default Font Size

Font Spacing

Default Font Spacing

Font Face

Default Font Face

Reading Theme

Default Theme (White)
You need to Log In or Sign Up to have your customization saved in your Literotica profile.
PUBLIC BETA

Note: You can change font size, font face, and turn on dark mode by clicking the "A" icon tab in the Story Info Box.

You can temporarily switch back to a Classic Literotica® experience during our ongoing public Beta testing. Please consider leaving feedback on issues you experience or suggest improvements.

Click here

When I was 18 (and still a virgin) my mom bought me a fancy YSL shirt because I had mistakenly told her I had a date. I didn't want to wear a smart shirt - I was a gothic punk and wanted to keep it real! Anyway, to keep my mom happy I wore the shirt to my date. That night I lost my virginity to this crazy Aussie sexpot.

FIVE YEARS later, I was at college and needed a model for my graphic design end-of-year project. I was introduced to Stacy. Voted Miss Waverly Girls High in 88, she was a slender brunette with an adorable face. She came over to my house and we took photos; some of which I used. Some were really sexy and I still have one in my porti.

Once they were developed I went to the townhouse where she lived with her parents to give her copies for her modeling portfolio. I decided to dress like a bohemian photographer and wore the same YSL shirt – albeit untucked – to my "meeting".

Her mom and boyfriend dutifully went into the garden - which was plainly visible through the one-way tinted windows - leaving us alone in the lounge. While showing her the pics I could see her mom and the boyfriend chatting away, drinking orange juice and looking at the garden.

At this point Stacy "bumped" her left boob against my arm. I politely ignored her until it happened again. I pressed back and her knee rubbed against my leg. In seconds we were grabbing each other and it wasn't long before she turned around to rub her bum against my cock. Lifting up her uniform skirt I pulled her panties aside and began to feel her up.

"Ooooh," she squealed. Without further ado I pulled my hard cock out of my pants and pressed it against her pussy lips. We managed to get it in with little difficulty and I fucked it in and out as hard as I could.

"Look," she panted. I glanced over, suddenly realising that her mom and boyfriend were still waiting for us outside! They couldn't see us but was so sexy watching them while we were fucking and we came soon. Stacy went to tell her mom we'd finished, then walked me to my car.

FIFTEEN YEARS later I went to visit an old friend. After a few drinks she said, "I've got a present for you," and she took out the shirt. "I borrowed it from you years n years ago so now you can have it back." It was the same YSL shirt. I was surprised, but OK. Why not? It still fit.

At this point I had never made the connection between wearing the shirt and getting laid on a regular basis every time I did. But over the years it just became obvious...

ONE DAY I met an ex of mine. She'd just got back from her honeymoon and we went out for dinner. We had a lot of catching up to do. A nerdy girl from a wealthy academic family, she'd gone abroad to study, which is where she met her husband to be. It had been years since we'd seen each other, and as the wedding had been overseas, I'd not been able to go.

As we were going to a fancy restaurant I decided to wear the YSL shirt my mom had bought me the night I lost my virginity. Hours later, dinner and chitchat aside, my ex's ankles were on my shoulders and I was ramming my hard dick in her dripping cunt. Her big bouncing tits hung over the sides of her chest, while she moaned for more.

That night she smeared her cunt juice over my lips, anointing me as her "sex slave", and in the two years that her new husband was away on assignment overseas, we would fuck n suck every chance we got! This included:

• fingering her to a silent orgasm while sitting at a table in a restaurant - in front of her sister and her new fiancé. They were suddenly very busy with the menu "Red or White wine, darling?;

• cuffing her to the front door security gate of her apartment, then fucking her 'til I came. As she had not come yet I made her grind her clit against the bars until she orgasmed. She moaned and bit the bars as her thighs slammed again and again against the gate. Lucky no-one called the neighborhood watch.

She seemed to like the feel of metal against her cunt. That, combined with a love for outdoor sex, ensured things got horny on a regular basis!

A New Year's Eve party was a case in point. Everyone was dressed in costume, the wine was flowing and the music was great – chill-house vibes & African Jazz. Eventually, she and I found ourselves in the kitchen looking for a drink and a chance to be alone. I came up behind her and started to squeeze those glorious boobs.

"Mmmm" she moaned, leaning back, rubbing her ass crack over my swelling cock. I hadn't worn any underwear so it was easy to become fully erect. That, combined with the booze and the naughty stolen moment meant that my cock was bigger than it had been in a while. "Oh! Is THAT all for me?!"

I reached over her shoulder to slip my hand down the front of her dress. Reaching her nipple, I pulled it erect between my thumb and forefinger. She leant back even further and soon her floppy tit was lifted off her chest. Panting, she whispered in my ear, "It hurts! But don't stop. Never stop."

Just then the hostess walked in. We stopped, and ran out, laughing. Of course things had gone too far for us just to ignore what had happened and we snuck into the hostess' bedroom to continue our tryst. Lying her down on the bed I pushed her skirt up her thighs. Her cunt smell pervaded the room. Wet and dark purple in colour, the lips were splayed wide open and I just had to have a taste.

Of course, as luck would have it the hostess chose THAT moment to open the bedroom door. We hastily got up and made a beeline for the front door. Of course this meant we were not going to ring in the New Year with our friends, but we were to horny to care.

Climbing into my dark blue BMW she told me through tightly clenched lips; "This is too much. You must make me CUM or I am going to scream."

I laughed and told her "You, my little sex nut, are going to have the cum of a lifetime."

I got in the driver's seat and off we went. Accelerating, I drove us towards the highway. There was a special neighbourhood I wanted to go to if I was to carry out my plan successfully.

As we sped into the flow of traffic she reached over and took my cock out of my pants. Jerking it hard, she leant over and sucked the knob into her hot little mouth. It always amazed me how those tiny lips could stretch over my dick. Not that I was thinking about that of course. Drive. Drive. Keep your attention on the road, I thought, as her head bobbed up and down.

Soon we came to the offramp and I took us down into the streets of a quiet, well-to-do suburb.

Stopping the car in a particularly dark street, I turned off the engine and we kissed for a while. Stepping out of the car I walked over to her side, opened the door and took her hand. "Out you get, my lovely," I said.

Standing between a clump of bushes and the BMW she probably thought we were going to go behind them for a quickie.

With no warning, I spun her around and pushed her forward onto the fender of my BMW. She tried to struggle, but I had one of her arms pinned uncomfortably behind her back.

Gathering her hair in my fist, I pushed her face against the windscreen. "If you want to cum you had better do as I say."

"Now put your leg up on the car," I ordered, pushing her thigh upwards before she could move a muscle. She was left with one foot on the pavement, and one thigh on the car. Her skirt was pushed up and I yanked her panties aside. The crack of her arse, the star of her anus and her slit were on full view.

"I want to see your clit," I said.

She reached between her legs, spread her cunt lips open and showed me her clit. It was hard - red and swollen. I leaned over and licked it then worked my way up to her bum hole. Then I stepped back and slapped her naked bum.

"Fuck the car!" I yelled!

"What?!" she laughed. I slapped her arse again, loudly. "Rub your cunt against the car. I won't tell you again! Do it! Do it now!"

She began to rub, stepping up on her toes to get a better angle of attack. Her slit was pressed against the fender at the point where it sloped over the engine. She clenched her arse muscles and ground against the car.

I looked down at the scene in front of me. I could hear the ticking of the cooling engine, but it was her flexing bum cheeks that really got my attention. "Mmm, that looks good," I said. I slapped her again and slipped a finger into her cunt.

"Let's see how long you can last now, slutwife" I said.

"Ahhh," she gasped.

"Oh, that's good," I said pushing my finger in and out of her, helping grind her cunt on the car. I could hear the squelching juice of her pussy as she neared her orgasm.

"You look so sexy. Now, I want you to cum. Do it, slut. Cum for me."

Her body convulsed as she came against my car. "AAAAAnnnn..! she wailed, her pussy walls gripping my finger as she came,

I pulled my finger from her dripping cunt and smacked her bum again before climbing back in the car. She was still sprawled across the fender. Panting heavily she lifted herself up. "You arsehole!" she shouted. "What if someone drove past!? You are so irresponsible," she snapped.

I laughed. "Come on. Get in. I leant over and took her hand. "The night isn't over yet. My balls have a few hot loads for you before I take you home."

End of Chapter One

Please rate this story
The author would appreciate your feedback.
  • COMMENTS
Anonymous
Our Comments Policy is available in the Lit FAQ
Post as:
Anonymous
1 Comments
RedHairedandFriendlyRedHairedandFriendlyalmost 18 years ago
Thanks

Your story has been mentioned on the New Story Review Thread found on Literotica's Bulletin Board in the Author's Hangout forum. ~ Red

Share this Story

Similar Stories

First Fuck of a Beautiful Young TS Sex with a lovely young tranny.in Transgender & Crossdressers
She Has a What?! Teaching his roommate how to use her assets.in Transgender & Crossdressers
Girl in a Miniskirt - Carla A very 'English' story: miniskirts and school uniforms. in Exhibitionist & Voyeur
Asian Adventure Ch. 01 A long overdue meeting with an online friend.in Transgender & Crossdressers
School Girl Sexy crossdresser has some fun with Daddy.in Transgender & Crossdressers
More Stories