losing virginity

The 22 Year Old Virgin

tangled

Twenty-two.  Not 40.  But had I not intervened, he may have waited until he was forty.  I did my duty and rescued him from such a fate.

It was unseasonably cold that winter.  We’d actually had a smattering of snow, which is unusual in the deep South.  The roads were icy and I was sequestered at home…with my parents.  So the weekend after the winter storm, I was more than ready to get out and heat things up a bit.  My cousin invited me to visit him for a decadent weekend.  He was in his junior year of college at the University of South Carolina and there was always a party going on.  He had a wide variety of friends.  Men/women, gay/straight/bi, wild as hell and super nerdy.  He was a social butterfly who enjoyed them all.

I loved visiting him.  He always had a plan, an agenda, of what we would do for fun.  He was a small town boy with big city tastes.  He loved to live on the edge.  And I walked that ledge on the edge with him.  We started the weekend by going to a few parties on campus.  We both had a good time, but it wasn’t at the level of our typical shenanigans.  We were infamous for doing some crazy shit, like tip-toeing out of someone’s bedroom before their lover got home.  In fact, he was the same cousin who had taken my to the beach, where I had my first three-way.  Our stories were scandalous and I was slightly disappointed that the weekend began so tame.

Saturday was full of shopping, noshing on eclectic food and drinking.  I spent a copious amount of money on a sexy black cashmere sweater.  It was the perfect color for my milky complexion and I wore it with a micro-mini Pucci-print miniskirt and black thigh-high boots.  I was fierce.  We went to a few 18+ nightclubs, but nothing kept our attention.  It looked like the night was a wash, when we happened upon a party on the Horseshoe.  My cousin recognized one of his classmates, Tom.

Tom was a finance major, who was graduating that year and planned to continue on and get his MBA.  He wanted to intern with Barclay’s in London and eventually open his own consulting firm.  The man was smart, articulate and incredibly sexy.  Tall.  Dark.  Handsome. (And his feet were HUGE..just sayin’).  But he was a nerdy mess when it came to chatting up a girl. He could talk about the world of finance and currency exchanges, but flirty banter made him a blubbering mess.

And that’s when my agenda changed.  I had to have him. I was attracted to Tom in a different way.  He had this charm and innocence about him.  He was successful and if I am being real with you guys…he was a Kennedy.  Not related to the royals, but he had an air of aristocracy that made him seem like he was one of them.  I could tell there was a bad boy lurking  beneath the surface.  And it was my duty as an American citizen to find that beast and bring it out…you know the whole, “not what your country can do for you, but what YOU can “do” for your country” thing.  I took that seriously.

I sat next to him at the party and engaged him in conversation about European currency.  This was before the Euro and he had a vast knowledge on the subject.  My knowledge was basic, but enough to impress him that I had an interest (he seemed to pick up that I had a little bit of nerd lurking beneath my bad girl persona).  We talked for hours.  He was starting to become comfortable and sat a bit closer to me on the couch.

I peered into his big brown eyes, hoping to lure a kiss out of him, but he was still very nervous.  I realized that this project was going to take some time.  We parted ways that night with a long hug and quick peck on the cheek.  And that was okay.  It gave me something to do the next weekend.

We talked every day that week.  I could tell he was smitten with me.  We planned to meet again on Friday afternoon.  Both of us were finished with classes by 2:00 and it was less than an hour away.  I told my cousin I was coming up again for the weekend and he was happy to have me there again.  I told him not to plan much, as I was going to focus on Tom.  He understood, as he’d met someone new and was busy planning their agenda together.

Friday arrived and I showed up at his dorm in that sexy cashmere sweater and my best “good butt” jeans. He was visibly nervous, but I got him talking about something in his comfort zone and he began to relax.  We decided to try a new restaurant in the Vista.  We had an amazing meal and he was such the gentleman.  Honestly, it was a perfect date.  Part of me felt guilty for having such tawdry plans for him later.  He was such a good guy.

After dinner we stopped in at a few parties and talked with some of his friends.  He seemed more and more relaxed as the night went on.  We finally made it back to his dorm (his roommate was away for the weekend) around 11:30 that night.  We sat on his bed and talked some more.  Once again, I looked into his eyes, hopeful that he would kiss me, but not expecting him to make the first move.

He brushed the hair from my face.  I could feel his hand shaking as he touched my face and pulled me towards him.  Despite his nervousness, the kiss was perfect.  And it went like a wildfire from there.  We were locked in a fit of passion.  The kissing was sensual and erotic.  I began to wonder why he was so unsure of himself.  He certainly seemed like he knew how to kiss a girl.

He pulled me onto his lap as his big strong hands massaged my back.  My black sweater had a plunging neckline and I felt like my breasts would spill out from how he passionately touched me.  I could feel his hardness through my moist jeans and I was eager to see him fully naked.  To take him all in and study his form.  Soon, I removed his shirt and he took off my sweater.  His hands trembled as he unfastened my lacy pink bra.  He looked at my bare breasts in awe before clumsily fondling one as he attempted to lick my nipples.  He eventually found his groove and before long, we stood before each other naked.

“I don’t know how to tell you this” he whispered nervously.  “I’m still a virgin.”

I already knew, but didn’t let on.  “You are?” I asked

“Yes.  Someone broke my heart my last year of high school and I’ve not had the nerve to ask anyone out here at college.  I have buried myself in studies and just put it out of my mind.  But I am ready.”

He walked towards me, held my face with both hands, looked into my eyes and said, “I want you.”

Let’s just pause for a minute and reflect, shall we?  1.  This man is gorgeous.  2.  He is a virgin.  3.  He wants me…ME.  4.  And he’s a Kennedy.  

I gently kissed his mouth and dropped to my knees, taking him into my mouth.  He was rock hard and almost lost his balance.  I asked him to sit down on the bed as I resumed my position.  I realized that he’d never experienced anything like this before.  I knew he may orgasm quickly, so I slowed my pace, allowing him to enjoy each and every second of the experience.  He closed his eyes and moaned in pleasure.  I didn’t allow him to finish, because I wanted him to direct how he wanted his first time to go.

He pulled me on top of him, as he fumbled with a condom.  I politely took it from him and had it on in less than a minute, with expert skill.  He wanted me on top.  I straddled him and slowly guided him inside me as he pulled my hips onto his.  He watched me ride his cock.  He looked into my eyes and then watched every move of my body on his, in amazement.

He came quickly and was most apologetic.  I assured him that it was okay.  He was ready to go again soon and we fucked all night long.  Him on top. Me on top again.  Him from behind.  More oral.  Showering together.  We finally went to sleep around 4:00 am and woke up and fucked more at 7:00 am.  We stayed in bed the entire day.  Exploring.  Feasting on each other.  Sharing our desires.  It was one of the best weekends of my life.

It rained for most of the weekend and when weren’t worshipping each other, we were intertwined in the sheets, watching it rain from his large dorm window.  We never got dressed or went out…We ordered pizza on Saturday and  Sunday.  We didn’t want to miss a moment together.  But eventually we had to untangle ourselves and get back to reality.

I left that evening a bit confused.  I’d been with virgins before and I enjoyed the role as a teacher. But this felt different.  I really liked this man.  He was everything I wanted in a boyfriend and the sex was amazing.  I remained in deep thought as I drove home in the rain.  The moment I arrived home, the phone rang.  It was him.  He wanted to make sure I made it safely.

We talked for hours that night and I think that was the first time I fell in love.  We stayed together as a blissfully happy couple until the summer.  He landed that internship at Barclays and headed out for a summer in London.  We tried to stay together despite the distance, but I was ready to move on.  I was not ready to find the One.  He could have certainly been the One.  But I was young and adventurous and we both decided to see other people.

Eleven years later, I was on a beach near Charleston, SC.  I heard someone call out “Tom?  Tom Kennedy? Is that you?  I haven’t seen you since USC!”  I looked up and saw Tom talking with the man who had called his name.  He was 20 feet away from where I was sitting with my family.  OMG.  He was still gorgeous.  He was married and had two beautiful children.  I was there with my husband and son.  I decided not to say anything and I made an excuse for us to change locations, because it would have been too much to see him again.

I prefer to remember him as he was during that rainy weekend in the winter of 1991.

 

 

(Photo, Pinterest)

The Student

Winter of 1988.

We met through a mutual friend, who said we were perfect for each other. He was almost 18 and I’d just turned 16.  His father was a dentist.  He attended a school in another county.  He was nice-looking, very tall and very smart.  His name was Joe.

Joe had all the traits of a confident, popular high school senior, except that he was painfully shy and socially awkward in certain scenarios.  He was most awkward when interacting with girls. I seemed to put him at ease.  And, I took him on as a project.

Our relationship began as a friendship.  We would attend different school functions in support of one another.  It gave us time to hang out and get to know each other in a comfortable setting.  But I found myself becoming more and more attracted to him.  I found myself thinking about him sexually.  Wanting him.

He was just so innocent.  So shy and nervous.  When we crossed the line from friendship into interest, our first kiss was a bit of a disaster.  But we kept at it and he grew more confident.  We began going on dates and instead of going to the movies as we said we were…we would end up in the backseat of his Volvo, making out to whatever was on the radio.  We never consummated the relationship.  He was very hesitant to go there.  I seemed to understand why.  I think it was performance anxiety.  He was still a virgin.

Joe knew that I was experienced.  More experienced and confident than he was.  I clearly knew what I was doing and he still fumbled about when trying to get into my jeans.  So I began to take on the role of coach, mentor, trainer to him.  You see, I knew the relationship we shared would not go anywhere.  Although we had so much in common on the outside, we were wired differently.  I knew that he couldn’t give me what I needed, even at such a young age…I knew who I was…what I craved…I understood my dark desires.  And Joe was truly too nice of a guy to handle my tar black soul.

I remember showing him how to remove my bra with one movement of his wrist.  How to caress my breasts, teasing my nipples.  I showed him how to kiss me on the neck to turn me on.  I demonstrated how to successfully get inside my jeans, with minimal effort. I explained a woman’s anatomy and showed him what felt good.  I let him experiment on me.  My body was like his laboratory and he was an eager student.

I remember the first time I took his cock in my mouth.  He came in a matter of seconds.  He was so embarrassed and apologetic.  But I explained that the only way to increase his endurance was through practice.  So we kept going there.  Eventually, he showed me what he liked.  He began to understand himself and his desires.  He learned how to communicate what he wanted from me.  How he liked it when I licked his shaft before taking him deep in my throat.

We carried on like this for weeks.  Each “date” was a tutoring session.  I taught him how to please me manually and orally. He became accustomed to giving and receiving pleasure.  He became more confident. He was morphing into the young man of my dreams.  But still, I knew it wouldn’t work long term.

One night after a long playdate in his car, he looked at me and said, “I am ready”

I was confused and said, “Okay.  I need to get home soon.  Let’s go.”

He said, “No.  I am ready to have sex…with you.”

I remember thinking how proud I was of him…that he not only knew he was ready, but he said it.  He told me.  I was impressed with his confidence.

I said, “Okay.  When do you want to do this?”  I felt like a teacher scheduling the final exam.

He said, “I will pick you up on Friday.  Be ready.”

Friday quickly arrived and I readied myself for our date.  I spent more time getting ready than I typically did for our sessions.  I wanted this to be special for him.  After school, I borrowed my mother’s car under the premise of getting hairspray at the store, but really, I bought my first pair of black thigh high stockings.  They were so opaque they were almost like tights and looked great under the black skirt I wore.  I felt confident and sexy.

He arrived a few minutes early and spend time chatting up my parents.  They liked his squeaky clean appearance and the fact that he came from a good family.  I rounded the corner from the hallway to the kitchen and our eyes met.  He was wearing a white Polo button down shirt with jeans.  He looked great.  He saw me and I could tell he was pleased by the way he looked me over.

We left my house around 7:30.  Instead of going to our favorite restaurant, he drove me to a place we’d never visited before.  It was close to his dad’s practice and had just been purchased by a developer (today there’s a car dealership there).  The road was clear, but completely deserted.  It was perfect.

Joe got out of the front seat without saying anything and walked around to open my door.  He took me by the hand and I assumed we would be moving to the backseat.  But first, he pinned me to the car and kissed me like he never had before.  I was shocked and excited.  He opened the door to the backseat and before I got in, he reached up my skirt and pulled my panties off…never uttering a word.  He then guided me into the car, shut the door and made his way to the other side.

He sat next to me and held my hand.  We rarely held hands, but it was nice. For a while, we just laughed and talked.  Then he looked at me, as he brushed my hair from my face and said, “I want you.”

Even though I was his teacher.  His mentor.  I felt a tinge of nervousness.  I was nervous about going all the way with him. He slowly unbuttoned his shirt and laid it across the front seat.  He then carefully removed my sweater, and then my bra. We kissed and he pulled me on top of his lap.  He fondled my breasts and teased my slit.  I felt his hardness through his jeans and asked if I could taste him.  He opened his door and removed his pants outside, turning to face me in the car.

“Come here.  You know what I like.”

I sat on his side of the car and sucked his hard cock from the open door.  It was intensely hot.  He held my face and knelt down to kiss me.  Then he said, “Lie down and scoot back to your side of the car.  I need some room.”

I felt him mount me and for the first time, I felt him inside me.  He was rather well-endowed and filled me quite nicely.  Neither of us said anything.  We just looked into each other’s eyes and sank into our own rhythm.  He pulled my legs up and went deeper.  We never lost eye contact.  I knew when he was getting close to orgasm.  I could read it in his eyes.

He stopped and took me by the hand to pull me up.  He then got back into the car and sat down for me to straddle him.  I was still wearing my thigh highs and sat atop his lap, easing him into my sex.  He held my body tightly as I began to move up and down on his hard shaft.

He broke the silence, “How do I feel?  Do you like how I feel?”

I was eager to give him feedback, “You feel wonderful.  You fill me up and I don’t want to stop riding you.”

Hearing that turned him on as he grabbed my hips and began moving me to his rhythm.  Faster.  Harder. Deeper.  I came almost instantly and he was not far behind.  I will never forget the look in his eyes as he unloaded in me.  How intense. How amazed.  How grateful.  How sated.

Afterwards, I stayed on his lap and we held each other.  He nuzzled himself in my long hair and breathed me in.  We shared a certain closeness…an intimacy.  Something I’d yet to experience, and I later realized what a profound effect it had on me. Finally it was time for us to go.

On the way back, we stopped at a drive thru and ate.  We had been so eager that we forgot to eat.  We laughed and joked on the way home.  And as usual, he walked me to the door and gave me a goodnight kiss.  But there was something different in the way he walked…carried himself.  He was a man.  And at the time, he was my man.

Eventually our relationship fizzled and we went our separate ways by the Spring.  He graduated that year and moved cross country to attend college.  One day, I received a letter from him.

The first page of the letter talked a lot about his life in college, his new girlfriend, his family and then on the second page…written as a separate note, was a letter thanking me for taking the time to show him how to treat a woman.  He referenced everything he learned from me and how I made his first time so special.  He went on to say that if he lived to be 100, he would never forget that night in late February where he lost his virginity.  He would never forget how patient I was with him.  He said in the letter that I was more than his first time, I was his first love.  He closed the note in a way that was closure for both of us.

It will be 28 years this February and I’ve never looked him up on social media.  I have never attempted to find his number or contact him in any way.  I drove by his dad’s practice and noticed his sister had taken it over, since his father retired.  I don’t want to know Joe now.  Our time and our purpose was long ago.

I want to keep him alive in my memories, just as I remember him.

in the car

Humble Beginnings…

The year was 1985.  And I found myself on a deserted dirt road, in the backseat of his white Monte Carlo.  I loved the way his lips felt on mine.  I loved how he gently sucked on my tongue when we kissed.  How he patiently guided me through each step.  After all, it was my first time.  We had been messing around for weeks, but this was it.  This was the night it was going to happen.  We didn’t talk about it, or plan it.  But we both knew.

He picked me up from the skating rink, where my trusting and naive parents had just dropped me off moments before.  I walked with such confidence.  I knew what we were going to do and I felt ready.  I got into his car and we drove to our usual location.  The dirt road was pitch black and I remember how the car shook from the gravel beneath the tires.  I remember the smell of his cologne.  We were both quiet during the drive and on occasion, I would catch him looking at me.

He pulled over to the place by the large oak tree.  We began kissing and quickly moved into the backseat.  I recall him taking off all of my clothes.  The seats felt cold on my skin as he laid me down on my back.  I braced myself for him.  I’d read Cosmo.  I’d watched movies.  I knew it would hurt the first time.  Suddenly I felt his mouth on me, as he spread my legs wide, massaging my clit with his tongue.  I didn’t know how to react.  I was shocked and aroused.  I began to moan with pleasure  It was unlike anything I’d ever felt.  But before I lost myself in my first real orgasm, I felt the weight of his body on mine as he opened me wide with his hips and entered me.

I will always remember the pain.  The pressure.  The feeling that he had penetrated more than my body.  That he had pushed himself into me again and again and how with each thrust I became more aware of every sensation.  I could feel myself becoming more wet, more excited with each movement.  I wanted more of him.  I found myself shedding my outer skin and morphing into an insatiable beast.

A beast I have been ever since.

That fateful evening in July, I lost my virginity and began a journey into decadence, almost possessed with lust.  Craving knowledge.  Craving experience. Craving sex.

And that was just the beginning.

lolita