Month: September 2015

My First Three-Way

Ah…my first three-way. It happened when I was on vacation.  You know, they don’t make a postcard that says, “Wish You Were Here for the 3-Way” or “Greetings from the Menage a Trois” do they?  I remember like it was yesterday, although it’s been a while.

It was the summer of 1989, Myrtle Beach, South Carolina.

I traveled there with my gay cousin who was a few years older than me. He gave the outward appearance of being responsible and trustworthy. My parents, his aunt and uncle, trusted him inherently…which meant I was allowed to travel with him…at 16 years old. It was the summer before my senior year. As we’ve established, I had quite a bit of experience under my belt at this point (no pun intended).  Our plan was to live it up for the weekend, although our families thought we were on a mission to shop at the outlets and tan on the beach.  I don’t know if we ever even made it to the beach itself.  But we did some serious shopping.

We arrived in the early afternoon.  The first line of business was to make sure my fake ID was believable.  My cousin, Joe, had a friend (Carl) who worked the door at several nightclubs at the beach.  Carl looked at it and said it passed the test.  Next on the agenda was finding something appropriate for me to wear.  We were venturing out to a few gay clubs and I needed to ditch the virtuous ensemble I’d packed as part of the farce, for something a bit more outrageous.  We went to a local shop and I found a black halter that highlighted my large, tan, perky breasts.  It was very sexy and it was perfect with the cutoff jeans I’d brought.  We had dinner and hit the first club around 10:00.  The music was great, but the club was dead.  So we left.  The next club had a drag show for the evening and there wouldn’t be any dancing until after 1:00 am.  So we went to yet another club….and just like in the story of Goldilocks and the Three Bears…

This one, was JUST RIGHT.

It was full of beautiful men.  Men of all ages.  All races.  All backgrounds.  And I assumed that they were all gay. Within minutes of arriving, I felt someone caress my bare back and I turned around to find a gorgeous Latin man. He was a great dancer and we had instant chemistry.  But…he was there with his lover and I could tell he was not pleased with our connection.  Javier said he was bisexual, but his boyfriend was the jealous type, so we parted ways a few dances into the evening.  The music in the club was great, but I just wasn’t feeling it.  I asked my cousin to take me back to the hotel.  I knew he was far from being finished with the evening and I didn’t want my lack of interest to ruin his good time.  He was more than eager to take me back because he wanted to change clothes.

Our hotel was right in the middle of “the strip” which is the main road in Myrtle Beach.  It is party central on most nights.  Our room faced the street below and I had a perfect box seat to watch the festivities below.  Before my cousin left to head back out, he handed me a bottle of Bacardi and said….”Help yourself, doll.  Just save me some.”  I decided to try it and I made myself a rum and coke and ventured out the balcony.

The sites below were like being on Bourbon Street during Mardi Gras.  It was Girls Gone Wild…Guys Gone Wild…flashy cars…flashy clothes…loud music and lots of partying.  I was entertained by my view from the top and I sat there for a bit enjoying the buzz around me.

“Hey there, ma’am.  What are you doing by yourself on a Friday night?”  he yelled.  I didn’t pay him any attention, because I didn’t know he was talking to me.  He yelled again, “You in the black shirt…you okay up there?”  I then realized he was talking to me.

I leaned over the rail and said, “Yes!  I am fine.  Just enjoying the view from up here.”  I didn’t realize that my breasts were on full display as I leaned over the balcony.  But he did.

“You have an extra chair up there for me?” he asked.  And being the foolish, adventurous teen I was….I said, “Of course I do.  You coming?”

We met in the lobby.  His name was Chris.  He was a cadet at the Citadel.  He was tall, muscular and a bit cocky.  I hand’t noticed, but he was with a friend, who was very quiet and reserved.  Not bad looking, just a bit shy.  And I know how dangerous this is…but I invited them up.  After all…they were from the Citadel and that was an elite school.  They couldn’t be that dangerous.

We arrived in the room and went to the balcony.  We sat out there, drank rum, told stories and enjoyed each other’s company. His friend, Rick, began to loosen up a bit and we all had a great time.  They left to get another bottle of Bacardi as we plowed through the first one.

When they came back, Chris recommended we play a drinking game.  I was all for it, but the only game I knew of (remember, I was only 16) was Quarters.  Chris had another plan.

“I have another game in mind.  It’s like Quarters, but it’s called…’Drink, Drink, Fuck.”  I knew exactly where he was going.

And I immediately went into beast mode.  

I smiled shyly and then stared him in the eye and said, “Drink, Drink, Fuck, huh?  Come now, Chris.  Let’s just skip the drinking.”

And it was on.

Chris stood me up and began kissing me, while his (now not so shy) friend, Rick, stood behind me.  Chris unbuttoned my jeans while Rick took off my shirt.  I wasn’t wearing  a bra and they both tended to my ample breasts.  I had Chris first.  I could tell he was experienced.  He flipped me over on my stomach and he fucked me from behind.  Rick watched us for a while and I asked him to come sit in front of me.  I sucked his cock while Chris continued to fuck me.  Chris lasted a long time and I could tell Rick was about to come, so I stopped sucking him and let Chris finish.  The entire scene was so hot.  When he finished I told him to wash himself and come back to me.  Even back then, I disliked the taste of latex.  While he was in the bathroom, I mounted Rick and began grinding on his hard dick.  I was so into the scene that I was on auto pilot. Chris returned and I turned myself into reverse cowgirl so I could face Chris’ cock.  I rode and sucked them until we all came in an absolute frenzy.  It was amazing.

Afterwards, Rick and I lay there while Chris went back out on the balcony for another drink.  Rick got up to join him and I said, “Send Chris back in here.  I want more of him.”

The rest of the evening is a bit of a blur.  I do remember that we fucked for what seemed forever.  Rick sat in the chair watching us while he stroked his cock.  It was such a insanely hot exchange.

Just before dawn…the second bottle of Bacardi was gone.  We had almost used an entire box of condoms and I was spent.  And despite the night’s activities, both of these naughty soldiers were still gentlemen.  They got me some juice from the lobby, helped me put on my pink satin gown and tucked me in the bed.  They left as the first light began to shine on the balcony.

So ladies and gents… that was my first three-way.

Two guys.  One girl.  Two bottles of rum.  A box of condoms.



The Calling

For as long as I can remember, I have been fascinated by sex. Most of my early introductions were through cheesy late night cable. By the time I was 10 years old, I had already seen the entire Emmanuelle series, and many other soft-core porn selections.  I enjoyed watching and learned quite a bit about “anatomy” along the way.

In 1987, the TV movie, Mayflower Madam, aired.  I recall watching it with my mother.  I was almost 15 at the time and my mother had no judgement when it came to TV or movies.  (She really didn’t get it…never allow a 7 year old to watch the Exorcist on Halloween night…just sayin’)  We both watched this story of Sydney Biddle Barrows, and how she opened her own  escort service.  I was hooked.  (No pun intended).  How interesting.  How intriguing.  I remember thinking to myself, “I could do that.  I could be an escort, a call-girl.” Even at the tender age of 15, me…a straight-A student, thought being an escort would be a fun career for a fun-loving gal like myself.

Fast-forward to 6 years later.

It was a hazy summer evening in mid-June.  I was sitting on a porch with friends, solving the world’s problems. As usual, I was dishing on some poor loser I’d just dumped.  There was always a story.  I plowed through men like water and I was always on the lookout for my next victim.  I was becoming a bit harsh and bitter, seeing men as a past-time and closely guarding my emotions, as not to get hurt.  I was in the middle of my story about this latest tryst when my friend, Brian, spoke up and said, “As much as you like sex, you should really get paid for it.”  I laughed and said, “Sure.  Wish I could! I’d be rich and famous…or infamous.”  And while the rest of my friends laughed at my comment, Brian was quiet.

“Do you really want to get paid for sex?”  His tone was serious.  I didn’t know if he was about to lecture me, save my soul or offer me money for a fierce blow job.

So for kicks, I said, “Yes, Brian.  I would love to get paid.  Sign me up.”

One week later, I began my journey as an escort.

Brian wasn’t the pimp.  He was not involved in the business at all, but he knew a lesbian couple making a killing working for a service.  They were madly in love with each other, but very short on cash, so they began working as escorts (with men or women) to make ends meet.  One of them was in college and the other worked as a dental assistant by day.  They seemed to enjoy the work and referred me to the Madam.

Her name was Gina and she was a fast-talking woman with an endearing way about her.  Looking back I think she was on some type of drugs, but I was naive to it at the time.  She liked me immediately and hired me on the spot. (The interview was in the parking lot, in her car at a local nightclub.)  She had asked me to bring a copy of my drivers license with me for her records, which I did.  (She kept this in case of emergency).

After the interview and job offer, we discussed pricing, payment and work hours….

Then she looked at me and said, “Are you ready to work tonight?”

I was not expecting that at all.  My first thought was about my underwear…was I wearing the cute ones?  Were they sexy enough?  Was I sexy enough?

And within 3 seconds I answered her, “Yes, Ma’am.  I am ready”

My first call with with a man in his early forties that owned a used car dealership.  He was a heavy drinker who had just divorced his third wife.  He was decent looking and smelled a bit like my father….it was likely the Old Spice he wore.  Gina gave me a “work” name to protect my identity.  I didn’t choose my name…she did.

That night, I was Tiffany.  I wasn’t a fan of it.  I asked her why she chose that name for me.  She replied, “It has a certain innocence and charm.  And you are charming.  And you look like the girl next door….there’s nothing harsh about you.”

So I did it.  I liked this new identity.  I found myself developing a persona around my new name.  I played a bit coy and innocent.  I could tell he liked it.  It made him feel like my mentor, my teacher.

And to be very honest, I was nervous.  I mean how do you have sex with someone within minutes of meeting them?

I quickly realized that this whole thing, sex for money…this  is Sales 101.  It is needs-identification.  Knowing what he wants.  Listening.  Validating the need.  And closing.

For this gentleman…he wanted a “pretty young thing” to help him get over his latest relationship.  He needed someone who would make him feel good, with no strings, that would be out of his life as quickly as they’d arrived. And I fit the bill.  But he ended up wanting me to stay the entire night.  I cleared it with the Madam and they negotiated a set price.  During our rest breaks we talked…we laughed…we noshed on room service…and then we fucked again.  And again.

The Sunday morning sun peeked through the drawn hotel curtains as I was getting dressed to leave.  In the light of day, we were both all business.  One of Gina’s cardinal rules was to call her upon arrival and before departure.  So I called her once he paid me, and she verified that I had been given the proper amount.  Then she asked to speak to him.  He was most complimentary of his time with me and asked her if he could tip me.  And he did.

I walked out to my car that morning with $1300 in my pocket.  I immediately drove to the designated meeting place to give Gina her portion ($400) leaving me with my share, $900…$800 for the evening and the $100 tip.

Not bad for my first time.

I remember going shopping later that day…just as I had the day before.  I didn’t feel any different.  I didn’t feel ashamed.  I didn’t question the morality or the legality of my choice.  For me, it was a job…an assignment.  I accepted it.  I completed it…and I got PAID for it.

It was Father’s Day, 1994.  I had just arrived at my parent’s house when my pager buzzed.  It was Gina.  She had another assignment for me later that evening.  So I had dinner, enjoyed the visit with my parents and excused myself for the night.

By 10:00 pm, I had already completed one assignment as was booked for two more.  I finally returned home around 2:00 am.

The grand net total for my inaugural weekend….

Four assignments and $1600 in my pocket.

Damn, that was easy.  A girl could get used to this….


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.