I stripped out of my clothes and prepared an enema before my bath.  A long hot bath with a martini is the perfect way to enjoy a late afternoon before a night out.  After toweling off, I laid out my wardrobe for the evening. I chose my very short red tank dress, my camel hair double breasted pea coat, black sheer stockings and black high heel pumps.  I chose a strapless black bra and matching pantie/gaffe and garter belt.  I over accessorized with bold bracelets, necklaces and a choker.  I laid out my longest wig that was jet black in color.

I ate a light supper, then I got myself ready by doing my make-up and touching up my nails. I attached my breast forms and got dressed.  I checked myself out in my full-length mirror and thought I looked pretty damn hot for a sixty-year-old cross dresser.  I downed my second martini and felt a nice gentle buzz from the cocktails. I filled up my handbag with all the essentials, slipped on my coat and headed out.  I looked at my phone to check the time and it was approaching 7:30 PM.

A short stroll to the “T” (Boston’s mass transportation system) to board a train to downtown Boston. The train arrived almost immediately after my arrival at the station and I boarded a car that was about half full. I chose a window seat in an empty row and slipped off my coat as the train was pretty warm. At the second stop, I moved my coat out of the empty seat next to me allowing a middle-aged man to sit down.  I saw him eyeing my legs that were fully exposed due to the shortness of my dress that barely covered the top of my sheer black nylons.

He didn’t say anything to me other than hello, but his eyes did not stop looking at my legs.  Before we arrived at the next stop, he had shifted his left leg so that it was touching my right leg.  I knew this was intentional, but I did not give him any indication that I noticed the contact.  We remained in this position until the next stop and as the train braked to slow down, he brushed his left hand on my right knee. Again, I did not act like anything had transpired, but made a plan on what to do next. 

I grabbed my coat that was between me and the window of the train and laid it over his lap.  He looked at me and I just put my finger over my lips to indicate he was not to say anything.  I made a quick survey of the train and there were a few people near our seats.  There were two people sitting behind us, one in front of us and an older man across the aisle in the window seat.  I slipped my hand under my coat and placed it directly on his crotch. I started to massage his cock through his trousers and felt it starting to stiffen. I reached over with my other hand and unfastened his belt, then unbuttoned his pants and gently pulled down his zipper.  I removed my left hand and inserted my right hand down his underwear and could feel his bare cock. I started stroking it very gently as it got harder and harder. 

“Tell me when you are ready to cum,”  I whispered in his ear.

I continued stroking his cock for about three or four minutes.  We stopped at another station once but no one boarding sat very close to us. His cock was very hard and I could only imagine how big it was as I could not see it with my coat covering him.  After a couple more minutes, he rubbed his hand on my arm indicating he was ready.  I took a quick look around and the coast still looked clear.  I bent over and slid my head under my coat and quickly put the head of his cock in my mouth as I stroked the base of his shaft.  From this position I could see he was about six inches long and the veins on his penis were an indication he was ready to cum.  My mouth was only on his cock for seconds when the first shot of cum went off and into my eagerly waiting mouth. I starting sucking stronger and continued to stroke him as more cum kept shooting in my mouth.  A full load of his juice was now in my mouth and I swallowed every drop.  I removed my mouth from his dick and sat up letting him take care of getting his clothing back in order. 

“That was yummy!” I told him. 

A moment later he handed me my coat as the train pulled into my station stop.  I stood up and gave him a little peck on the cheek and promptly strolled down the aisle and off the train.  My grin stretched from ear to ear as I exited the station into downtown.

It had been a couple months since I had been in downtown Boston.  I loved the atmosphere and the energy level of business people, tourists and the locals.  I walked from the train station to Copley Plaza and went into one of the major hotels located there.  I know from experience that hotel bars and frequented by business men on trips, looking for lonely ladies.  The bar in this particular hotel was small with only about ten seats at the bar itself and several small tables.  I found an empty seat and my eyes adjusted to the dim lighting.  The bartender approached me and I ordered a Ketel One Martini with a splash of cranberry. As he made the drink, I slipped off my coat and hung it on the back of my bar stool and hung my handbag on a hook that was attached to the bottom of the bar.  I sat back down and crossed my legs showing off my legs almost to the top of my stockings. I sipped my drink and perused my phone waiting to see if anyone would approach me.

Halfway through my drink a gentleman sat down in the seat beside me, even though there were several other seats available.  We exchanged hello’s and he ordered some type of fancy bourbon on the rocks.  As he was ordering I took a look at him…he was probably around fifty-five years old, with salt and pepper hair, probably six feet tall and in pretty good shape with only a small amount of fat around his mid-section.

“Would you be a dear and watch my drink and coat as I run to the ladies room?” I asked him.

He paused a second and looked at me, but his eyes barely met mine as his glance went downward from my face to my chest and then to my legs. 

“Of course, I will keep a close eye on everything,” he said with a wink.

I stood up slowly deliberately allowing my dress to ride up a few inches so that my garter straps were visible and grabbed his hand in mine.  “Thanks, honey.  I will be right back.” I told him.

As I walked away, I could feel his eyes watching my back side as I headed to the rest room. I felt sure that he would be my first score of the night, well second if you count the stranger on the train.  I used the ladies room to pee and to check my make-up and hair.  A small touch up of my lipstick and a brush through my long sexy hair.  I felt confident as I strolled back into the bar and took my seat.

“Thank you” I said. “My name is Cassie.  Are you staying at the hotel?”

“Hi, I am Dave. Yes, I am here on business,”  he replied. “Can I buy you a drink?  We both are empty.”

I leant over next to him, placed my hand on the inside of his thigh and whispered in his ear. “Dave, excuse me for being direct, but what I really would like to do is go to your room and suck your cock.”

“Well, that sounds better than a drink,” he answered.  “Now, I have to be direct too.  Is that going to cost me?”

I looked at him in the eyes. “Only a hot load of cum, baby.” I smiled.

Within five minutes we were in the elevator and he pulled me close as the car went up.   He grabbed my ass and leant down and kissed me on the lips.  I immediately opened my mouth and welcomed his tongue as it probed all around the inside of my mouth.  I couldn’t wait to get to his room, but enjoyed the lustful energy he provided with his tongue and lips. I could feel his cock was already rock hard as he pressed his groin into me. We finally reached the seventh floor and we left the elevator and he pulled the key card from his wallet.  As soon as we were inside the room, I laid my coat and handbag on a sofa as he started to undress. Once he had taken off his shoes and unbuckled his belt, I pulled down his trousers and freed his cock from his boxer briefs. 

I guided him to the bed and as he sat down, I pulled off his pants and underwear watching his seven-inch steel hard cock pop to attention.  I crawled on the bed and went to work.  I started stroking his cock and licking his balls, raising his arousal and mine. I devoured his balls as I stroked his cock as he begged me to suck his dick.

My lips gently kissed the purple head of his dick and then I put my lips around it and started to gently suck his rod. I deep-throated the entire length of his cock and made loud slurping sounds. After three deep plunges all the way down his rod, I removed my mouth and showed him the saliva drooling from my mouth. I started stroking his cock fast and went back to licking and sucking his balls.  My arousal was so strong, I couldn’t stop sucking his balls and stroking his hard cock. Then I went back down on his dick and again took him all the way down my throat five or six times. 

“Fuck baby, that feels so good.  Suck me, make me cum in your mouth,” he begged.

I went back to work and picked up the pace of my sucking and plunging.  I could feel his cock pulsating in my mouth ready to explode.  Then he shot his load.  A huge thick load of cum shot into my mouth and I slurped and drank it as fast as he kept spewing inside me.  I slurped and sucked until every last drop was milked out of his cock and then I licked and slurped any cum left on his dick.

Achieving my goal of a hot load of cum, I excused myself to use his restroom.  I grabbed my bag and touched up my face and lipstick and then proceeded to walk out and grab my coat.  Before he had a chance to talk or ask for more, I went to the bed kissed his cheek and said goodbye.  The whole encounter was less than ten minutes and I was on the prowl for more.

I walked down the hallway heading towards the elevator still savoring the taste of Dave’s cock and cum in my mouth. It was now around 8:30 and I thought I would head to an old hotel across the street that featured an old-fashioned Irish Pub.  I arrived in the lobby and exited the main doors and crossed Boylston Street and entered the old establishment. The pub was near the entrance and I strolled in looking for my next encounter.  I removed my coat and put it on my arm and strolled into the pub. It was much larger than the other bar and more crowded.  It was also much louder and I squeezed up to the bar and found a stool open.  I hung my coat and sat down crossing my legs and hooked the strap of my handbag underneath me around the chair seat.

It took about three minutes to order my martini and it was worth the wait. The bartender poured a perfect martini, just the right amount of vermouth and just a touch of cranberry and perfectly chilled.  I scrolled with my eyes the patrons at the bar.  To my right were two men in business suits and to my left was a threesome, two men and one woman.  The woman was sitting next to me and one man was standing behind her and the other guy who was seated on her left.  The men looked much younger than the woman who appeared to be my age.  She was dressed more conservatively than me in a beige business suit with the skirt stopping just above her knee and a white button blouse under the matching suit jacket.  The guys were dressed in business clothes but had taken off their suit coats and had loosened their tie.  She appeared to be drinking a cosmopolitan and the men were drinking some type of whiskey. 

The business men to my right appeared very conservative, dressed like lawyers in pinstripe suits and red power ties.  They were talking business and did not even notice my arrival. I turned my attention back to the threesome on my left and overheard the guys chatting up the older woman.  She turned to look at me and rolled her eyes as to indicate they were a little obnoxious in their approach. I smiled back at her and raised my glass towards her.  She picked up her glass and we “clinked” the two martini glasses in salute.

I leant close and asked softly “You don’t appreciate two younger men fawning over you?”

“They are probably younger than my own son,” she whispered back. 

“Hi there, beautiful.” The guy standing behind her interrupted. 

Now that I was included in the mix, we all chatted about little things and the guys each offered to buy us another round.  I was really starting to feel pretty drunk from all the martinis and was enjoying the flirtation banter with the young men.  I looked at them more closely and estimated they were in their late twenties and had probably had at least three cocktails each from their disposition and their speech patterns.  They were telling Vicki (we exchanged names earlier) and I that they were from New York City and were here for only one night.  They were hoping to go out to a club and enjoy themselves, but found this pub and were now going to hang out here instead. 

I excused myself to go to the ladies room and Vicki said she had to go too.  We strolled off together and once in the rest room we chatted about the young studs.

“So, are you taking those young studs back to your room, or are you going to theirs?” I asked her.

She smiled at me and said, “I am not sure, I have to admit I am pretty horny and they are pretty good looking, but I have never been with two guys before.”

“Well, I could join you and make it a foursome, if you like,” I replied.

We discussed some details and we worked out a plan.  We relieved ourselves and fixed up our lipstick and returned to the bar.  To our surprise our guys had been joined by two other men that appeared to be the same age or maybe even younger. We sat back down in our seats and both of us became more flirtatious with the young guys. I was letting one of them rub my thigh as we chatted and I made a couple of gentle touches of his groin area just to let him know I was wanting more.

Vicki and I had another martini and I could tell she was getting more tipsy and also more animated.  She had removed her suit jacket, unbuttoned one of the buttons on her blouse and had let her skirt ride up to middle of her thighs.  One of the guys had one of his hands on her hip while chatting with her.

“Vicki, I would like one more martini, but I was thinking I would rather enjoy it in your room,” I said.

“Great idea, Cassie! Any of you boys ready to leave too?” she replied.

“How about we go to our room? We have a suite and there will be more room to relax.” one of the original guys suggested.

Within five minutes with drinks in hand and bar billed paid (by the guys) we filed in to the elevator. It was a snug fit with six of us all in the elevator and it made it convenient for me to start rubbing the crotches of two guys.  Vicki was making out with another one and the last guy was standing behind me grinding his crotch into my ass.  I didn’t remember any of their names and was so buzzed that I wasn’t sure who was grinding me and who I was fondling.  We eventually made it to the room and Vicki and two guys headed off to the bedroom while I guided a pair to the couch.

The guys started stripping off their clothes as I chugged my martini.  They sat naked on the couch and I approached them as I lowered myself to my knees.  I looked at two big cocks already standing straight up.  I grabbed one in each hand and started stroking their long cocks up and down.   Then I lowered my mouth on the guy on my right and engulfed his whole cock on my first plunge down his shaft. I repeated this move over and over as I kept stroking the cock on my left.  Then I switched and swallowed the cock on the left which was even bigger than the seven-inch cock I had buried in my mouth earlier. I was so horny and drunk I could not suck his cock fast enough.  I kept plunging up and down on his hard cock loudly sucking and slurping on it while now stroking the cock on my right.

 I made room on the couch for me and knelt down in between the two guys and went back down on the guy on the left. I lifted up the back of my dress and with my butt facing the guy on the right I told him to shove his big cock in my ass.  I picked up my pace of sucking the big eight-inch cock as I heard the sound of spit behind me.  He must be lubricating his cock with his saliva, I thought. Then I felt the tip of his cock poke in my ass and I shoved back against it sliding the full length of his rod deep in my ass.  He grabbed my hips and started a piston movement of shoving his cock in and out of me as I continued to slurp and suck the other cock.

I removed my mouth from the big cock inside and started to stroke his hard dick so I could fully enjoy the hard ass fucking.  The loud slapping sounds of his pelvic hitting my ass when he thrust his big cock inside me filled the room.  I started licking the ball sack of the guy in front of me while I continued to stroke his cock and get my ass pounded.

“Oh, fuck baby.  I am going to cum so hard in your tight butt!” the guy behind me uttered.

I felt his hips slam against me and felt him hold my hips tight as he groaned and shot a hot load of cum deep in my ass.  He pulled out of me and I spun around and took his softening cock in my mouth to seep out the last of his cum.  Exposing my ass to the other guy, he took advantage of the situation as he grabbed his cock and slid the head of it in my cum filled ass.  Some new sounds entered the room as I saw the other two guys leave the bedroom and approach us.

“The other girl fell asleep.  I barely got to start to fuck her after Sean came in her pussy,” one of the guys was saying.

“I already fucked this one up the ass and now Tyler is doing the same,” replied the guy who had just shot his load in me.

“Fuck, here I cum!” said the guy as he really started to pound my ass with his huge cock.

I shoved my ass back to meet his strokes and felt him buried deep in me and then another shot of cum filled me again. 

“Who’s next, who wants to fuck my ass now,”  I moaned

I assume it was the guy who didn’t get to finish fucking Vicki who climbed on the couch behind me replacing the spent guy. He guided his cock into my well cum lubed asshole with little effort.  Soon he was pounding away fucking my ass and another cock appeared before my face.  I eagerly started sucking the other cock and then a second cock was beside it.  I stroked one while I sucked the other and felt the cock of the third guy entering deeper in my ass.  He had to be as big if not bigger by the feel of the deep penetration inside me. I altered between sucking the two cocks and stroking the other as the one behind me got into a rhythm of giving me long fucking strokes. Pulling his cock nearly all the way out and then holding my hips to thrust deep inside me.  I felt him rise up off of his knees and get to a standing position on the couch and pulled my hips up.  I had to let go of the other cocks to insure my small cock and balls were fully concealed as he started to fuck me incredibly hard with all the leverage, he created by standing.

My body was shaking from trying to hold my ass up with my hands on the couch and the powerful thrusts from him as he hammered my ass with his large dick. He must have shoved in and out of me thirty times until I felt his hardened dick explode in me.  He let me down so I was on my hands and knees and I was able to start shaking and control my breath. 

I pulled up to a sitting position and looked at the guys.  They were all pretty spent after all the fucking and drinking. 

“Wow, guys.  That was fun!” I said. “Let me go check on Vicki.” 

I grabbed my coat and handbag and went to the bedroom, closed the door behind me and looked at Vicki.  She was starting to wake up.  I told her to wait there I needed to wash up in the adjoining bathroom.  Feeling so slutty (in a good way), I took a plastic glass from the sink and proceeded to remove my gaffe.  I squeezed out of my ass and watched the glass I held underneath me slowly fill up with the loads of cum I had taken in my ass.  This action filled about one-fourth of the glass with white man juice.  I couldn’t resist, being such a slutty girl and chugged the glass down.  I could barely taste the flavor, but felt the creamy thick texture of my favorite substance as it slid down my throat.

I heard a knock on the door and I quickly slid my gaffe back in position.  Vicki was standing there, she had put her clothes back on and we worked together to make both of us presentable.  I told her I would take her to her room, but we would have to make the walk of shame first.  We strolled out of the bathroom and bedroom and into the living room of the suite.  By this time two of the guys had left and the two remaining were the first ones we met at the bar. 

“Thanks for the drinks and all the fun, boys!" I said. “Enjoy the rest of your stay in Boston.”

We left the room and went to Vicki’s.  She was feeling better, just tired.

“Cassie, I am so disappointed.  I barely got any action, here I am going to be slutty with two guys and I fall asleep, how embarrassing.  I was really looking forward to some fun,” she said.

I smiled and said “Well, it’s still early.”     

To be continued...