Ian's Story, Part Two

The thing I found most surprising about Ian after reading his flash drive memoir was how much more sexually experienced he was then me.  I suppose it’s my ego getting in the way, but when we fucked that first time in his basement apartment I didn’t think he was all that experienced.  I mean he knew what to do, but it wasn’t all that special.  To be frank, he used a little too much teeth when he blew me and he had a little trouble getting hard enough to fuck me.  To be fair, he had been drinking, so maybe the booze had some effect on his ability.  The second and third times were much better, but even still, I would never have guessed that he did it as often as he claims.  His time as an escort and dancer do explain why he is so comfortable about being naked in the house, even with my brother around.  I’m just grateful he put on pajama bottoms when Aunt Sarah was here.

My First Escort Job

I hadn’t been on the escort service’s call roll but a couple of days when I got my first assignment –I was to meet a middle-aged business man from Harrisburg, PA at his hotel, the Milford Plaza in the theater district for a matinee performance at Lincoln Center then an early dinner.  The dispatcher at the agency told me to arrive by noon, dress nicely and what, exactly, I  was contracted to do; that if anything else happened afterward, that was between me and the client.  I was to collect my escort fee of $500 up front (I would get half of that) and any other fees I was free to negotiate on my own, though the management requested a 10% “finder’s fee” if anything more was negotiated. 

I remember it was a warm Saturday.  I wore nice slacks, a cream-colored buttoned shirt with the top three buttons undone, a sports jacket and my favorite loafers.  I had been given his room number in advance, so I went directly to the elevator and rode up to the fifteenth floor.  I remember my heart was pounding in my chest as I knocked on his door.  I introduced myself as “Danny”, shook his hand and entered his room. 

He said his name was Ted Williams and that he was in insurance.  I looked him over discretely as I’m sure he looked me over.  He was in his mid- to late-forties and in fine shape for a man his age.  His brown hair was slightly thin and there was a trace of gray at his temples and in his mustache.  All in all, he was fairly good-looking, but his best days were behind him.  I mentioned the fee and he was quick to take out his wallet and hand me five one-hundred dollar bills.

Once I was paid, I asked him to tell me a little about himself.  He said he came to New York every couple of months and that when he was here, he liked to have company.  He said there was nothing worse than going to the theater or a restaurant alone.  He asked me about myself and I spun some story about being on my own and trying to get into acting, but classes were expensive.  He nodded as if he understood than he asked me if I had ever been to the opera.  I said I hadn’t but would like to try it.  (I already knew where we were headed, but didn’t know what we would be seeing.)

We took a cab to Lincoln Center.  I had seen the iconic buildings many times but had never actually been inside.  The interior of the opera house was a sea of reds and gold and for the next few hours Ted and I watched a performance of Don Quixote.  It was amazing!  I was familiar with the story, but had never seen it performed in such a way.  I can still hear the echo of some of the music from time to time as I daydream.

After the performance we took another cab ride downtown and Ted had his hand on my thigh all the way back.  I knew what he would want after dinner.  The question was, would I go through with it? The cab left us off in front of a fancy Italian restaurant only a few minutes’ walk from Ted’s hotel.  Dinner conversation was a little stilted, each of us trying to figure out what to talk about and failing miserably at it.

Finally, on the slow walk back to the hotel, Ted asked in a low voice if I would stay with him for the night.  “I have to go back to Harrisburg tomorrow and I don’t want to wake up alone,” he said.  “You don’t even have to have sex with me if you don’t want to, just sleep with me.  I want to feel your warm body against mine.”

It was sad, what he said, there was a terrible longing in his voice.  I looked down at his left hand to see if there was a ring, but there wasn’t; not even an indication where one may have been.  “You do know that isn’t covered in the escort fee,” I said softly.

He nodded as he looked down at the pavement.  “I put some money aside on the off chance you would agree.”  There was a long pause.  “Will a thousand be enough?”

“That will be fine,” I said, opening the door to the hotel and letting Ted in first.  We took the elevator back up to the fifteenth floor and were back in his room in minutes. 

Once in the room, Ted went to his suitcase and withdrew an envelope from an inner pocket.  I opened it when he gave it to me and counted the money inside – one thousand dollars.  I hadn’t held that kind of money before.

I put the envelope of cash in my jacket’s inner pocket and since I was going to spend the night, I took it off and hung it on a hanger in the “closet” – an open-air section of wall in the far corner.  I also took off my shoes.

Ted also got comfortable and we spent the next couple of hours sitting on the room’s couch watching some low-budget movie on the television and talking.  After a while, Ted ordered something to eat from room service.  Over burgers and fries Ted told me more of his life story – he had been married but they were not happy together, so after five years they got divorced.  It took him nearly another two years and several more failed relationships with women before he admitted to himself he was gay.  Back home there really weren’t many places to go and meet other guys which is why when his office offered him the chance to travel to New York every couple of months he accepted.

By the time he had finished his story, the burgers were gone and it was dark outside the windows.  Ted excused himself, and went into the bathroom.  After a few moments I heard the shower. 

I had been thinking about what do to about this moment for the past hour and now that the moment was here, I decided to go for it.  I quickly got undressed, putting my clothes carelessly on a chair, entered the bathroom and closed the door quietly behind me.  I slipped the shower curtain aside ever so slightly and stepped in.  I have always wondered if Ted somehow knew I was there because when I took the washcloth and began soaping up his back he just quivered slightly and let out a deep, contented sigh.  He stepped into the shower spray, washed the soap out of his hair and off his skin then turned around to face me.  His cock was thin and hard.  I knelt in the tub before if and kissed it right on the glands, just below the piss slit.  Then, grabbing his legs, I licked the hard shaft of his cock down to his balls and back up again before taking him into my mouth.  I hadn’t taken more than half of him into my mouth before he came.  Looking back on it now, I realize it was all that pent-up desire finally exploding, but back then it caught me by surprise. 

Ted was a little embarrassed that he came so quickly, but I told him not to worry.  Now that his first ejaculation was out of the way, his next one would be so much more satisfying.  He smiled at that.  Then he took the soapy washcloth and began washing me – first he washed my chest, playing with my nipples and tonguing each one.  Then he moved on to my arms, paying close attention to my armpits.  Then he moved on to my back and neck before moving down to my legs.  He paid particular attention to my ass of course, fingering my hole.  By the time he turned me around to wash my cock, I was very hard.  He washed it lovingly, sliding the soapy cloth up and down and around my balls.  Then he moved back to let the spray wash the suds away. 

I thought he was going to blow me there in the shower, but instead, he turned the water off, reached over for a towel and started drying me.  He took my hand, led me back into the room and sat in the chair by the writing table.  “I just want to look at you,” he said.  So I stood there, naked and hard, though losing my erection.  I tried to pose the way I had seen muscle-men do, but Ted didn’t like it, so I stopped and just stood there.  After a few minutes of Ted silently viewing me as if I were a work of art he got up, came to me in his nakedness, and began to stroke me; first with his fingertips up my arms and across my chest.  Then he kissed the nape of my neck and my shoulders.  It was all surreal and romantic.  Finally, after nearly fifteen minutes of Ted caressing and kissing me, he sank to his knees before me and took my cock into his mouth.  He was hesitant at first, as if mine was the first cock he sucked, then he became more confident, eventually taking all of me down his throat. 

I must have moaned too loudly because he stopped and lead me to the bed.  I thought he was going to push me down onto the mattress and fuck me, but instead he lay on the bed.  “Fuck me,” he pleaded.  “I want to feel you inside me.”

I tried to be as gentle with him as he had been with me, but he did not want that.

“No,” he said.  “Fuck me!  Do it hard!”

So I did as he said.  I pulled his ass cheeks apart and spat on his hole.  I positioned myself against him and pushed.  His ass resisted at first but I insisted and soon enough his ass yielded to my cock.  I began with slow, deep thrusts, pulling out almost completely before thrusting back into him.  Then I picked up the pace and started cursing at him.  “You like my cock up your ass, don’t you faggot!” and “I’m gonna fuck your man-cunt and you’re gonna take it you fucking shit!” and other things like that.  Soon he was moaning and gripping the comforter on the bed.  Sweat trickled down his face and pooled in the shallow places of his slightly flabby belly.  Then, without warning, his cock spasmed and thick milky ropes of his cum shot out, landing on his neck and chest, then on his belly. 

Sweat had been running down my back and dripping off my nose and when I watched Ted cum, I pulled out of his ass and climbed up on the bed, straddling him.  I forced my hard cock into his mouth again and he took it.  I fucked his mouth for a few strokes then pulled out because I knew I was close.  I beat off a few seconds, gripped my cock hard to stave off cumming, but it was too late.  I shot my cum all over Ted’s face and chin.

When I was done, I rolled off his and onto the bed beside him, breathing heavily.  Ted was breathing heavily too, but his hand found my softening cock and gave it a soft squeeze.  Then he got up and went back into the bathroom for another shower.  I sat up on the bed, looked at the clock on the bedside table, reached for the remote and turned the TV on to the news.  When Ted came out, dressed in his pajama bottoms, I stayed on the bed a little longer, letting him look at me in my nakedness.  Then, on a commercial, I got up and sauntered into the bathroom, giving Ted a good look at my ass, and took my own shower.  Afterward, I exited the bathroom toweling my hair dry and since I didn’t have anything to wear I just walked over to the couch as naked as could be.  What did it matter to me now?

When the news was over I went over to the bed, pulled off the covers and got under the top sheet.  “Aren’t you going to join me?” I asked.  Ted nodded mutely, turned off the TV and came to bed.  “Do you really need those?” I asked him, indicating his pajama bottoms.  Wordlessly, he slipped them off and stepped out of them, letting them stay on the floor.  His soft dick was tiny, no bigger than my thumb.  He got into bed and scooted up close to me.  I reached over and turned off the lamp. 

We lay next to each other in the darkness, Ted’s arm holding me close until his breathing became deep and regular.  Eventually he rolled over and I tried to sleep, but I’ve never been good at sleeping in strange places.  And trying to sleep with a virtual stranger?  Not so easy for me to do.  I lay there next to him as he snored softly, my mind racing.  I got up, went to the bathroom then checked to see if that envelope of cash was still in my jacket pocket.  It was.  I crawled back in the bed and tried to sleep, but couldn’t.  At least Ted’s body was comfortable to be next to. 

I must have fallen asleep at some point because the next thing I knew the world outside the window was bright.  I glanced at the clock on the bedside table.  It was still early; nearly seven a.m.  I lay there next to Ted for several minutes before Ted woke and smiled at me.  Then he scooted close to me again, the way he had when we first went to bed.  We lay like that, my front to his back, spooning my grandfather used to call it, for several minutes.  Then he pulled off the covers and got up out of bed.  I raised myself on an elbow.  “Would you like me to suck you off one last time before I go?”  He nodded and I swung my legs over the edge of the bed and sat up.  I grabbed his limp cock and gently pulled him over to me.  I played with his flaccid member until it was hard then took him into my mouth.  I was fairly sure I wouldn’t be sucking him for too long if last night was any indication.  And in less than a minute, he was breathing hard.  Then he sucked his breath in and his whole body stiffened.  I let his cock slip out of my mouth and started beating him off.  It only took a few strokes before he came, shooting his load onto my chest.  I wiped it off with the bed sheet.  When Ted was done he gave me a weak, embarrassed smile and went into the bathroom.  I beat off quickly, coming on the bed then dressed in the clothes I was wearing the day before.

“Don’t go just yet, Ted said coming out of the bathroom, a towel around his waist.  “I want to buy you breakfast.  Just let me get dressed and we’ll go downstairs.  And there’s an extra toothbrush if you want to brush before we eat.”  I thanked him and brushed the stale taste of morning and his cock out of my mouth while he dressed and then we had breakfast in a diner down the street.  Afterward, outside the diner, we shook hands and said our good-byes.  “Can I see you again when I’m in town next?” he asked hopefully.

“Sure,” I said, “I’d like that.”  I took out one of the cards the office had made up for me.  It had their number and my name on one side, hourly and day rates on the other.  We said good-bye again and I walked off toward the office on Thirty-Sixth Street to hand over their portion of my money.

I meet up with Ted again six weeks later, for an entire weekend that time, and every six weeks after that like clockwork for the next year and a half even though I left escorting after less than a year.  During those weekends, I took Ted to his first strip show, introduced him to leather and bondage (he was always the submissive, ever the bottom) and watched as he got his first tattoo (a Celtic knot design on the left side of his groin).  For his part, he took me to the theater, concerts at Carnegie Hall and museums and galleries.  We went to movies, amusement parks, the botanical gardens and the zoo.  At times it was going on outings with a father-figure.  But no matter where we went or what we did, he paid for me and always afterward I showed him my appreciation.  And whenever he returned to Harrisburg, he always gave me a little extra money.  “A gift” he would call it.  My visits with Ted eventually ended when he told me he was transferring to the Miami office and he asked me to come with him.  I had to tell him at that point that I was in a relationship, but that our time together had been special to me and that I would always remember him.  I could tell he was disappointed I wasn’t going to go with him but he also wasn’t surprised.

We corresponded briefly after he moved but that soon faded to the obligatory Christmas card. 

I haven’t seen him in years, but he did send a beautiful wedding gift and a note that said he had finally found someone, someone close to his age who appreciated the same things he did.  I’m glad for him.  I really am.