I hope you enjoy Sandy's continuing adventures. Please comment and let me know if I should include the next two chapters. Chapter 9: Joe’s Pizza
Sunday morning I got up pretty early. I decided to call a cab and go over and pick up my van from Glenn and John’s. After I got back I decided to do some sit ups, as I had not been exercising as much lately. A quick shower after my exercises and then I decided to get ready for my trip.
I spent a couple of hours packing as I was going to be gone for at least ten days. First I packed up all of my samples that I needed for my work appointments. Secondly I packed all my work clothes that required hangers in a garment bag. Next I packed a duffel bag that carried all my socks, underwear, jeans and toiletries. Lastly, I packed a suitcase with several of my “Sandy” outfits. In this suitcase I put all my sex toys I wanted to bring and my camera.
I got a call from Collette the girl I met last Saturday night and she wondered if I wanted to have a late lunch or early dinner. Since it was 1:00 and I had all my chores done, we agreed to meet at 3:30 for appetizers at a restaurant near where we met last weekend.
I had a couple of hours to kill and I decided to do my new favorite hobby, shopping. Whenever I had any free time from work, I would always go shopping and buy little items or new outfits. I was totally addicted to shopping in cheap stores trying to find bargains to expand Sandy’s wardrobe. So I took all my suitcases and sample cases down to the garage and loaded them into the van. I put everything in the back and this left both front seats open and the bench seat (middle row) of the van clear.
Today I went into an adult book store, because there was something I needed to have for my adventures. I stopped at a drug store and picked up more rubbers, KY, fingernail polish remover and a couple of make up items. Next stop was a small mall in Alhambra a town next to mine where Diane the bartender lived. I knew they had a photography store there and I picked up a tri-pod. Then I browsed some stores and I picked up a couple of new outfits between the stores. I packed up all the goodies into my suitcases except for the two new outfits and drove home.
I returned at 3:00, just in time to wash up and walk down to the restaurant to meet Collette. I arrived a few minutes early at the restaurant, a really nice place called The Tea Room. There was no one else in the bar except for a bartender and waitress so I sat down at the middle stool and ordered a beer. Collette walked in the door a few minutes later. She looked much better than I remembered. She was probably 40 years old, with long black curly hair, a very curvy body, with an incredible set of legs.
She was wearing a white denim skirt with a fuchsia sweater. The sweater fit tight across her chest showing off her incredible set of tits. She was wearing flat beaded sandals so her legs just went on forever. I stood up as she approached and gave her a kiss on the cheek.
“Hi Collette, you look fantastic!” I said. “I am so glad you called, I have been wanting to see you.”
“Thanks Tony, same with me. I thought we had a fun time the other night.” She replied.
Collette ordered a cosmopolitan. I loved these drinks, but never ordered them as they were very feminine. I did take a sip of hers, and within an half an hour she was on her third cosmo and I had joined her and was on my second. We had potato skins as an appetizer and then a spinach dip as well and were now full and were on our way to a nice buzz.
We talked about a lot of stuff; I explained that I was kind of a free spirit, not looking for relationships or commitments right now. She was separated from her husband for almost a year and was also enjoying the single life. We enjoyed a few more drinks and it was almost 5:30. I told her I had to go home, as I was leaving tomorrow. She offered to give me a ride home, but I knew she lived only a couple of blocks away, so I told her no.
I walked her to her car which was located in the second floor of a parking garage behind the restaurant. As she opened the door to her car, she turned to me and we kissed. It started out innocent, but in seconds we were really kissing hard. My tongue was in her mouth and hers in mine and we were holding each other very tight. She opened her back door and told me to come inside with her.
She had a big car with a huge back seat. We immediately started kissing and I stuck my hand on her thigh and rubbed up her leg. She spread her legs wider and I slid my hand up underneath her white skirt and felt her black thighs while maintaining a lip lock on her. I slid around so that my knees were on the floor of the back seat and slid her skirt up all the way to her waist. I slid down her white panties all the way down her legs and over her sandalized feet. I stuck my head between her legs and starting licking Collette’s pussy with my tongue. I went right at her clit and found a big thick clit that felt wet from her dripping cunt.
I continued to lick her clit and moved my hand up her thigh until I found her pussy and inserted my index finger inside her cunt. Her moaning increased as I continued to lick and nibble on her clit as my finger went in and out of her sticky and very moist pussy.
“Tony, that feels so good, don’t stop. Keep eating my pussy! She panted out between moans.
I didn’t stop; I picked up the pace and inserted a second finger inside her. I tried to mix my licking with a gentle bite of her clit. This sent shivers throughout her entire body and she grabbed my head with both hands and shoved my face right into her wet pussy. I shifted my position and started to lick the bottom of her cunt and crept my tongue into her ass crack and I felt her lift her butt up so that my tongue could find her puckered asshole.
When I found my target I moved my middle finger inside her pussy to try to find her “g spot”. At the same time I started sticking my tongue into her asshole. This time her shiver shook her body so severely Collette let out a huge pant and moan.
“Fuck Tony, what are you doing to me?” She screamed.
I kept working my fingers and looked up to see Collette pulling up her sweater and unfastening her red lacy bra. I kept my attention on licking her ass and repeatedly sticking my tongue inside her asshole. It was so tight and clean. Even though the light was dim, I could see her black skin and pink pussy and taste and feel the warm juices flowing from her cunt. I stuck my tongue as far as I could up her ass again and worked my middle finger inside her cunt and hit the magic spot.
Collette started pinching her beautiful big black tits and started moaning in ecstasy. “Fuck me baby, fuck me now.” She screamed in the car.
“No baby, I want you to come all over my mouth.” I said.
Seconds later Collette exploded in an orgasm. She had both hands on the back of my head and shoved my mouth into her ass and my tongue reached further inside her. My two fingers were going along for the ride as her whole body buckled and twisted and she moaned.
“Yes, fucking yes! Fuck I am cumming, so hard. I am still cumming. I can’t stop! Fuck my ass with your tongue, baby! Make me keep cumming.”
She was in an uncontrollable state for about thirty seconds, bucking and twisting on the car seat. I slid my head up and started playing with her tits with both my hands and lips. I had to taste and feel these beautiful big breasts. As I was kissing her, I felt her hands go down to my crotch and unbutton my pants. We shifted positions so that I was on the car seat and Collette wasted no time in stripping my pants down to my ankles and without a word came up and sat on my stiff cock.
My dick slid into her pussy so easy and she whispered in my ear. “I had to have your cock inside me. Now fuck me good we need to get out of here before we get caught.”
It didn’t take much as we were both so hot. She rode my cock and I bucked my hips so that she could feel my entire dick inside her pussy. We only lasted about two minutes and I could feel my cock ready to spurt a huge load of cum. Collette was in the middle of her second intense orgasm and it was sending me over the edge.
“Baby, I am going to cum so hard.” I said.
She immediately climbed of my cock and put my dick in her mouth to finish the job. In seconds I was shooting a big load of cum into her mouth. Collette was pulling on my cock to drain every last drop of cum out of me.
“How was that for a first date, honey?” She asked.
“I can’t wait for the second, baby.” I replied.
My first thought was I have another fuck buddy! This has been a good week for finding girls to have casual sex! But my second thought was she was the hottest girl I had fucked in a long time. She had the most beautiful skin, great body, perfect personality and didn’t want to get in a relationship. We kissed good bye, I promised to call her in a couple of weeks when I got back and I was gone.
I left Collette and started my walk home. It was just past sundown and I enjoyed the short walk home after a great fuck session with a new hottie. I arrived at my apartment and took a hot shower shaving my body all over to get ready for my trip. It was about 7:00 PM when I got out of the shower and I dried off and spread powder all over my body. I had never used powder before, but since I started shaving, I loved the fresh feeling it gave to my body after a shower.
I couldn’t wait to try on my new outfits I bought earlier. I poured myself a scotch and had a couple of sips. The first one I tried on looked very sexy. I had been inspired by the look that Jules had worn to Tango’s last night. I bought a short red and black plaid mini skirt and a white button down top that I could tie at my waist line. I liked how it looked with my new white bra and white tank top that I wore underneath. I also found some frilly white ankle socks and white patent high heel pumps during my shopping. I thought I looked very cute and sexy in my new outfit. I put it back in my shopping bag and tried on the second outfit. It was a denim mini skirt with a blue chambray button down shirt. I also bought short cowboy boots and a red bandana to tie around my neck.
When I started trying this outfit on, I knew I had to go all the way. I refilled my drink and I put on all the accessories including my new “hide the dick sheath”, panties, nude color thigh highs and tons of silver jewelry. I put on my make up and wig and was fully dressed up. I looked at myself in the mirror and was amazed that I looked better each time I dressed up. I poured another drink and thought of what I was going to do for dinner. I didn’t want a late night as I had to leave rather early tomorrow on my trip, so I decided I would order pizza. When I thought of pizza, I thought of my first adventure with Carlos, but I wanted something different.
I thought of a great idea. I grabbed a grocery bag and put in my bottle of scotch, a big baggie filled with ice and put my handbag on my shoulder and strolled out of my apartment. I remembered I had to return Sheila’s key to her apartment and I thought I would make a little adventure out of it.
I walked upstairs seeing no one in the hallways and opened up the door to Sheila’s apartment. It was exactly as I had left it yesterday. I put down my things and then I looked for her phone book. I found a delivery place I had never called before, I called placed the order and sat back to wait to see if I would get lucky again.
I passed the time by snooping around Sheila’s apartment. I did a more thorough job of looking through her lingerie and found a couple of items I missed the first time. Wow, I would love to see her in a couple of these items. But even more than that, I wanted to try them on myself. But that was going to have to wait for some other time.
When the intercom buzzer rang, my heart started to beat fast and I couldn’t wait to find out who was delivering my pizza. The voice on the other end of the intercom was very bland and I couldn’t tell anything about him. I gave him directions to the apartment and buzzed him through. Two minutes later there was a knock on the door and I opened it to see a very tall and young black man. He looked to be about 18 years old and was at least 6’ 2” tall.
“Hi, come on in.” I said.
I turned my back and started walking towards the dining room table. I could hear him step in and I turned around and saw him watching my legs in my short denim skirt. I instructed him to put the pizza down on the table and he looked down at me and said “Twelve dollars even for the pizza, ma’am.”
This was a first someone calling me ma’am. I gave him a twenty dollar bill and like Carlos the first time, I asked for three dollars back.
“I am sorry ma’am, but I only have a one a five and a ten.” He said.
“That’s fine, I will take the one. A nice young man like you deserves a big tip.” I said.
“Thank you.” He said.
He handed me the one dollar bill and again, I pretended to accidentally drop in on the floor. This time I bent over to pick it up so he could see all of my legs from the back. I could feel my excitement rising as I knew he was checking me out. I picked up the dollar and when I turned around I “accidentally” bumped into his hip with my shoulder.
“Excuse me.” I said. “I am so clumsy. I have already broken two glasses tonight and this is my friend’s apartment, not mine. She is going to pissed when she sees her glasses missing.” I giggled after saying this and picked up my drink and took a swig. “Maybe it is because I had too many of these, te hee.”
“Thank you again, ma’am for the tip. You are a very beautiful woman.” He said.
I set my drink down and walked by him towards the front door, when I brushed by him, I could see he either had the start of one, or was already posting a hard on. I remembered myself at that age and I got hard when I looked at a girl, so with my little show, I was sure he was getting excited.
I got to the front door, but he was not following me. He was watching me walk away.
“What are you looking at young man?” I said.
“I am sorry ma’am, but I was just looking at you.” He said.
I closed the door half way and looked at him. “Come here.” I said.
He walked over towards me with a very nervous look on his face. He was still carrying the “keep warm” box the pizza was carried in and he was carrying it in front of him at his waist line.
“What is your name?” I asked as he approached me and the door.
“Joe” he replied.
“What are you hiding, Joe?” I asked. “Are you getting excited watching me?”
“Yes ma’am. I should be leaving, I am sorry.” He stuttered.
“It’s ok, baby. Do you want to leave right now? I don’t think so.” I said. I leaned against the door and gently shut the door. “How old are you Joe?”
“I just turned 18.” He said.
“Really?” I asked in a very inquisitive voice.
“No, I am 17” he stuttered.
“Have you ever been with a girl?” I asked.
“Well, I have played around some.” He said.
I took the carrying box from his hands and threw it on the floor. I could see the conversation had not taken down his excitement level. I came up close to him and whispered “Do you want me to make you cum?”
“Yes, please.” He said.
I took him by the hand and let him to Sheila’s bed. I sat him down on the edge of the bed and unfastened his blue jeans and slid them down to his ankles, he kicked off his tennis shoes, so that I could take them all the way off. He was not wearing underwear and I could see the most magnificent cock in my life. It was so smooth black and shiny. It was like a rocket ship about 8” long and very thin. I couldn’t wait to suck it.
I laid him down on the bed and he was very quiet. I could tell how nervous he was, but also how excited. I spoke in a very authorative but feminine voice. “Relax baby, but promise me one thing. This is our little secret, I don’t live here and I can’t let people find out I was sucking cock of a minor in my friend’s apartment.”
“Yes ma’am, I won’t tell anyone.” He said this as I started stroking his cock. “Oh, wow, that is so good.”
I couldn’t believe the length it continued to get longer as I stroked it. I crawled up on the bed beside him and kissed Joe’s mouth. He didn’t kiss very well, but after about 30 seconds, he was getting the hang of it. His mouth started to anticipate my tongue and he started to wrap his tongue into my mouth. Throughout the long kiss, I continued to stroke his long cock up and down. He took is right hand and started to untuck my shirt from my skirt and I let him as I stroked his cock. He kept his hand on my stomach and then slid it under my bra.
“Sorry baby, I have small tits, but you can play with them if you want.” I said.
I stood up and unbuttoned my shirt and unfastened my padded bra that gave the appearance of tits. I left my shirt and bra on my shoulders and in the dim light, I was sure Joe could not tell he was about to suck on a man’s set of nipples.
He went on them like a baby starving for milk. He kissed them, sucked them squeezed them and his cock was getting ready to shoot. I wanted this cock so bad in my mouth that I pushed his hands off of my chest and his mouth as well and crawled down to his crotch. I placed his cock between my tits and used my hands to create a look of breasts rubbing up and down on his cock. His face was in ecstasy and he was ready to come.
I went down further and put his monster cock in my mouth and went down as far as I could on the first plunge. He was so ready to cum and I could feel it.
“Baby, I want you to shoot your cum all over my tits, ok?” I said.
I didn’t have to wait long as I lay down on my back and he straddled me and started to stroke his cock. After two strokes I got to see this big rod shoot a load of white cum all over my tits, chest and finally my mouth. I slurped up his sweet cum from the edge of my mouth and then scooped up a big load on my left tit and swallowed it
“Thank you, honey. I was so horny and you just gave me what I needed. How was that for a secret to keep? I asked.
“That was great ma’am. I have never had that before.” He said.
“Well if you ever get a delivery request for Sandy, you might get even more next time.” I said as I was licking off the last of his cum from the tip of his dick.
When I was doing this, I noticed he was getting hard again, but I knew I could not do anymore right now.
I pulled up his pants and he got dressed, I walked him to the door and gave him a big kiss. “Don’t forget you pizza case and don’t forget this is our secret.” I said as I escorted him out the door.
“Yes, ma’am.” He said.
And then he was gone. I washed all the rest of Joe's cum off my chest with one of Sheila’s dirty towels. I did a quick inspection that I did not leave anything. I packed up my bag with my scotch and ice and glass and my pizza and left her apartment. I locked the door then slid her key underneath the door and walked down to my apartment. I knew for sure that I was going to have an excellent road trip! Chapter 10: Drinking at the Hotel Bar
I felt very refreshed Monday morning and was very anxious to start my road trip. I knew I was going to be successful on my trip as the new line of product I received in New York was perfect for the customers I was showing this week in San Diego and Phoenix. I packed up my briefcase with all of my work papers. I grabbed a couple of beach towels, a blanket, my half empty bottle of scotch and my shopping bag with my two new outfits.
My Monday was uneventful. I had two appointments one in Carlsbad (north of San Diego) and one in La Jolla (very close to San Diego). I checked into a Holiday Inn in San Diego. At the check in desk I told the agent behind the desk my fiancé would be arriving later and would like her name on the room as well. I told them her name was Sandy Stirling. This was something I was going to do at all the places I stayed, in case I wanted someone I met as Sandy to call me at my hotel.
I borrowed a luggage cart and went to my room with all my suitcases. I got to my room and unpacked all of my suitcases. I couldn’t believe how many things I had brought, I had a full closet and two drawers were filled. I spent about a half an hour getting things together from my work day and headed downstairs. I had the front desk fax all my orders to the corporate office and I went to the bar in the hotel.
It was a nice small bar kind of dimly lit and featured a bar with about ten stools, three booths and a three pub style tables. There were about six guys in the bar at different places all with shirts and ties, a group of traveling salesmen like myself. I had a beer and an appetizer and then left. I stopped by the front desk to pick up the faxes I sent and went back to my room.
I took a shower and then selected an outfit to wear. I poured a drink as I chose and lay out a conservative outfit, but with some sexy elements. I wore a black skirt that went just below my knees, but featured a long slit in the back that went half way up the back of my thighs. I wore black fishnet stockings that were kept on with a black lacy garter belt. I chose high heel black boots that went up to the hem of the skirt. My top was a black wool sweater that was loose fitting in the top but tight at the waist. Underneath I had a black lace bra with a matching camisole and black lace panties with my “secret keeper”. I wore my black patent belt with matching buckle, gold jewelry and my henna wig.
I finished my third drink in my room and then I grabbed my black handbag with all my necessary items and walked to the elevator. I went to the lobby and entered the bar I drank in earlier. It was now about 9:30 and there were only two groups of guys left in the bar. They all looked pretty drunk, as they had been drinking for at least two hours watching a football game on the television. I strolled in and sat down at the bar stool at the end of the bar and closest to the entrance. Even though I knew I was totally passable, I still wanted to sit in a dimly lit section and a place for a fast exit, as this was my first time out in a public place by myself, other than a walk around the streets.
The bartender came over to me and was very nice. I noticed for the first time what a difference the treatment a woman gets in a bar versus a guy.
“What can I get you young lady?” he asked.
This was the same bartender that served me earlier and he had no idea I was the same person.
“Do you make a good martini?” I asked, batting my eyes a little.
“Sure, how would you like it?” He replied.
“I will take a Cosmopolitan with Stoli vodka.” I said.
“You got it beautiful.” He said this and turned away to prepare my drink.
I pulled out a newspaper that I brought down with me and opened it up to pretend I was reading. This gave me the opportunity to see what the two groups of guys were doing. There were two guys that were sitting at a table in the opposite corner from me and when I took a small spin in the barstool to look at them, they were watching the TV on the wall and really not looking in my direction. As I spun back to face forward, I checked out the two guys sitting about four barstools down on my right.
The one closest to me was looking at the TV, which was showing highlights of the completed football game, but the guy next to him made eye contact with me and smiled. I smiled back and then my drink arrived.
“Here is your cosmo, I hope you enjoy it. My name is Larry, if you need anything just ask” The bartender said. “Would you like to open a tab?”
“Sure, my room number is 312. The name is Stirling.” I said.
I sipped my drink and sent my compliments to the bartender for making a perfect cosmo. I read an article in the newspaper and had a couple of innocent smile connections with the guy further down the bar. The last smile was from both he and his friend. They were both around 45 to 50 and appeared to be drinking scotch or bourbon. There voices were loud but not obnoxious as they carried on a conversation about football and other “guy” subjects.
I lay down my newspaper and took another sip of my drink. It was going down very smoothly and as I got about ¾ done, Larry was back in front of me striking up a conversation about the hotel, how long was I staying, my name and other tidbits. I was polite in return and took the last sip of my drink when he suggested I have another.
“Sure, I would love another one, they are so good. Where is the ladies room? I will go while you make my drink.” I asked.
“Back out in the lobby turn right and you will see the sign in the hallway on the left.” He replied.
I stood up straightened my skirt so that I knew the slit in the back was lined up correctly and then strutted out of the bar into the lobby. As I turned to the right, I looked back to see both of the guys at the bar checking me out, but I pretended not to notice. I went to the bathroom and relieved myself in the first stall. It is a little challenge to do this, as I have to untuck my dick from the pocket and then re-engineer everything before leaving the stall. After finishing I touched up my mascara and lipstick before returning to the bar. When I arrived, Larry placed my drink in front of me.
“Sandy that drink is the compliments of the two men sitting at the bar.” Larry said.
I picked up the martini glass and looked down the bar. Both guys were looking at me and raised their glass. I said thank you and took a big sip of my cosmo. Larry made a very strong drink, the liquid only had a very pale shade of red tint. Obviously 90% of this martini was Stoli Vodka, another advantage of being a woman at a bar.
As I set my drink down the guys both got of their bar stool and walked down towards me together. I spun my chair to face them upon their arrival and the first one said “Hi, I am Bob and this is my partner Stan.”
“Hi Bob, Stan, I am Sandy. It’s very nice to meet you.” I said. “Thank you for the drink.”
When I extended my hand Bob took it in his and shook it gently, then Stan did the same. “Can we join you for a minute, Sandy?” Stan said.
“On one condition, you both need new drinks, you are empty.” I said.
They had no problem meeting my request and it was scotch they were drinking as Larry pulled over a bottle of Johnnie Walker Black label and fixed them two new drinks. I learned that Larry and Stan were in the communications business and they explained what they did, but I was paying no attention to this as I drank my cosmo very quickly. Before I even finished my second drink a new one was placed in front of me.
We carried on for about 25 minutes, I was now on my fourth cosmo, and they had each drank two more scotches since the moved down the bar. I suggested we have a shot and I thought Stan was going to fall down laughing.
“I am already shit-faced, Sandy.” He said. “A shot might do me in, but if you insist.”
We all laughed very hard at Stan’s joke.
“Larry, I want three Stoli kamikazes!” I said.
Larry was over at the table in the corner where the other two guys were signing their check and getting ready to leave. Larry came back behind the bar and started making the kamikazes. This is a shot that has chilled vodka and lime juice, very tasty and very powerful. He actually poured four shots and joined us.
“To my last customers!” Larry said and raised his glass.
We all chugged the drinks and smiled and laughed when finished.
Bob was now standing behind my barstool with his hands on my shoulders and Stan was on the barstool next to me on my right and his left hand was on my thigh as we laughed.
I rubbed my shoulders under Bob’s hands and he started to gently rub them as I asked them how long they were staying. I learned they were leaving tomorrow morning back to Dallas where they lived.
Bob was the more handsome of the two, but neither was fabulous. Stan was an average looking guy around 5’ 10 about 200 pounds, Bob was probably a little taller and thinner. Both wore sports coats and slacks and had dispatched with their ties long ago. Both had black hair with a touch of grey Stan was balding and Bob had a full head of curly hair.
Stan shifted his stool so that he was facing me and sitting sideways to the bar. This allowed him to change hands and in doing so he slid his right hand under the hem of my skirt and was touching my fishnet hose on the inside of my knee. I could see a bulge in his crotch as obviously he was enjoying the action. Bob was also trying to take some liberties and was sneaking his left hand down the arm of my sweater and rubbing the back of my left hand.
“I am sorry, but I have to go to the bathroom.” Stan said.
“Me too.” I said. As I stood up I grabbed Stan’s hand from under my skirt and led him out of the bar.
As we walking out the door I asked him “Did you like the feel of my leg, honey?”
He looked at me and smiled as we approached the alcove the restrooms were in. We were out of view from the hallway and I leaned against the wall and looked at my new very drunk friend.
“So are you going to kiss me?” I asked.
I didn’t have to ask again, as Stan walked forward and pressed his body against mine. He kissed me hard shoving his tongue in my mouth. His hands immediately slid between my ass and the wall and then tried to slide up my skirt so he could feel more. I slid his hands away and back as I kissed him passionately.
“Wait baby, good things come to those who wait.” I said. “I know you are married, are you sure that you want me?”
“Oh, Sandy, You are so hot, I wanted to fuck you the minute I saw you.” Stan said.
“Well let’s see what happens, you may get lucky, but I want to party for a while.” I replied. With this, I turned and went into the bathroom.
When I came out of the bathroom a few minutes later the alcove was empty and I walked back to the bar. Bob was sitting on my stool and I did not see Stan or Larry. But there were three new fresh drinks and three new kamikazes.
“Where’s Larry the bartender?” I asked.
“He is in the back doing some of his closing chores. They close in 30 minutes.” Bob said.
I walked up to him on the stool and whispered in his ear. “Your friend Stan wants to fuck me and he may be too drunk, what do you want to do?”
He turned my face towards his and kissed me on the lips and grabbed my ass cheeks through my skirt and pulled me closer throughout the kiss. I stepped back and smiled at Bob and I removed my lipstick from my bag. I touched up my lips and grabbed a napkin off the bar and placed it between my lips to leave a “kiss” on the napkin and remove the excess lipstick. Then I dipped a corner of the napkin in one of the drinks and wiped off the lipstick on Bob’s mouth from our kiss.
Stan returned a few seconds later and I handed him a kamikaze, then gave one to Bob and said “Cheers.”
We chugged the drinks and I could tell that I was a lot better off than my two friends. They were equally drunk and if the bar was not closing soon, I am sure Larry would cut them off. Speaking of Larry he was now back behind the bar and taking stock of the situation.
I sat down at the stool next to Bob and Stan sat down on my right. I felt Bob put his arm around my back and felt Stan try to put his hand in his favorite place up my skirt and stroke the inside of my thigh. They were both doing it very discreetly like they were trying to hide the fact they were trying to see how much they could do to me in a covert manner. I smiled at Larry and shifted my body so that Stan had better access to my leg and leaned closer to Bob.
Larry asked us if we wanted another round and I replied for everyone. “Yes the night is still young, I will have another and so will my new friends. Stan and Bob, you are falling behind, drink your drinks.”
Larry laughed and turned around to prepare the drinks. “You guys are so nice, buying me these drinks. I would only have had one or two, but you guys treat me like a princess.” I said this and then I leaned over to my left careful to place my hand on the inner thigh of Bob and gave him a big kiss on the lips. I could feel his crotch stirring as I kissed and grazed my hand between his legs. I turned to my right and kissed Stan, but instead of grabbing his crotch, I grabbed his hand under my skirt and slid it up so that it was feeling my bare skin above my stockings but below my panties.
After I kissed Stan I looked at his crotch and I could tell he had a big hard on. Larry returned with the drinks and I thanked him and took a big swig of my cosmo. Bob stood up and excused himself as he was going to go to the bathroom. He kind of stumbled so I said I would help him. I linked my left arm under his right arm and escorted him down the same path Stan and I had just walked.
When we reached the bathroom, I led him to the men’s room door and told him to do his business. He tried to kiss me, but I told him to wait for later. I returned to the bar and sat next to Stan and took a sip of my drink. Larry approached and said “Sandy, last call do you want one more, I am cutting off your friends.”
“No I am fine.” I said as I still had almost a full drink.
Larry brought the bill to Stan and he signed the tab to his room and must have left a generous tip to Larry based on the reaction from the bartender when he saw the tip.
“What’s your room number?” I whispered in Stan’s ear.
“218.” he replied.
I told Stan I would meet him in his room in 15 minutes, but would only be able stay a little while. He left after I assured him Bob would be fine. I kissed Stan on the cheek, thanked him again for the drinks and gave him a wink. Larry came over and thanked me for coming in and he hoped I would come down tomorrow night too. I leaned over the bar and gave him a kiss and told him I would get Bob up to his room.
I left the bar and headed for the hall way with the bathrooms and sure enough Bob was just walking back.
“The bar is closed and Stan paid the bill and went upstairs.” I said as I approached him.
A big smile spread across his face and I half pushed him and led him back into the hallway. I grabbed his hand and went further down the hall and saw an open door on the right. I entered the room and found a small conference room that was very dark. Bob followed me and I closed door leaving it only open about an inch so that a little light was in the room.
I immediately gave Bob a kiss and then went down on my knees and unbuckled his belt and undid his fly. I pulled his cock out of his underwear and started giving him a blow job for the ages. I went all the way down on his cock so that my lips were touching the base of his cock. It was about a six inch cock and felt wonderful in my mouth.
My tongue was all over his love shaft as I sucked him faster and faster. Up and down with my mouth wide open on the way down until I licked the base of the underside of his cock. Slowly I raised my mouth and sucked in on his cock as I raised my lips up the entire length of his shaft. Bob was moaning in delight and I replaced my mouth with my hand and started to gently jerk his cock up and down giving him an enjoyable hand job.
This freed up my mouth to take some time on his balls. I stroked his cock with my right hand and held up his hairy balls with my left and started to lick his ball sack and then underneath so that my tongue was almost up the crack of his ass. I licked back towards his balls and then very gently put one of his balls in my mouth and gently licked his ball while it stayed in my mouth. I let it slip out of my mouth and went back down on his cock. I stroked the base of it with my right hand and shoved it into my mouth as I went down on his shaft. His cock was starting to twitch and I knew he was going to cum.
“Are you ready, baby?” I asked.
I pulled my mouth away and stroked his cock and could feel the explosion coming. Bob’s cock started shooting cum all over my face as I stroked so all of his cum would shoot all over my face. Then I started to suck and lick all the cum that was still on his dick. I used my hand to scoop up some of the cum on my face and licked it all of my fingers.
Bob was exhausted and sat down on the floor of the conference room and actually lay down. I snuck over to him kissed him on the cheek and said good night, while he started to fall asleep with his pants around his ankles and his head under a table in the conference room. I slipped out of the room and went in the girls room across the hall way. I went to the sink and cleaned up my face, brushed my hair and applied some lipstick.
When I came out of the bathroom there was no one to be seen. I saw a stairway entrance at the end of the hall and I opened the door and climbed the stairs to the second floor. I found room 218 and gently knocked on the door. Stan opened the door with the security chain attached and looked out.
“Hi baby, are you going to invite me in?” I asked.
“Sure” he said. He removed the security chain and opened the door.
Stan had taken off his sport coat and his shoes. I turned off the overhead light and led him over to his bed where I gave him a gentle push so that he fell on to the bed. The bedroom lamp was not too bright, so I decided to take advantage of that and the fact that Stan was almost passed out drunk.
“I was trying to stay awake”. Stan said. “Why is a hottie like you coming to my room?”
“Things are not as they always appear, Stanley.” I replied.
I had Stan sit up on the side of the bed and I unbuttoned his shirt and slipped it off his body. I kissed him on the side of his face and slipped his t-shirt over his head. I started kissing his chest and downward to his belly button where I unbuckled his belt. Then I unbuttoned his pants and unzipped his fly. I pulled down his pants and underpants and slipped them down around his ankles and off of each foot. Then I pulled his socks off and let him sit on the side of the bed.
He was really tired, so instead of sitting, he lay on his side on the bed, but looking at me. I unzipped my boots and pulled them off and Stan sat up to get a better look. I took a few steps away so the light was not as good as I slipped my sweater over my head and took if off of my arms. Next I unzipped the side zipper of my skirt and let it slide down my body. Here I was in a black cami with black lace panties and garter belt with black fish net stockings standing in front of a man.
Stan’s cock was rock hard and standing straight up. It was a great looking cock, big and fat and was calling my name. I took a step towards Stan and he lay down on the bed again and looked at me with total lust. I took a couple more steps forward and asked him “Do I look ok?”
“Oh my god baby, I have never been with a woman like you. You look so sexy.” He replied.
I came up to him on the bed and lay right on top of him and gave him a deep kiss. I slid my tongue in his mouth and licked the roof of his mouth with my tongue. I was wondering if he could taste the cum of Bob in my mouth, but I think he was beyond making that connection. I stopped the kiss and moved my tongue to his ear and stuck it in his ear. He was moaning with pleasure and was trying to grab my ass. I was being careful that he would not feel my own cock as I wanted to keep him unknowing the truth.
I reached over and turned off the lamp and now the room was very dark. I slid down on him so that my ass was straddling his waist and rubbing against his hard cock. I bit one of his nipples on his very hairy chest and sucked on it as he started to rock his cock against me. I could feel the friction of his cock against my panties and could feel his cock getting closer to my ass. I slid down past his cock and started to lick his stomach and then I put his cock in my mouth.
Now I could feel how long of a cock he had. It was wide and hard to get my lips all the way around it and I had to work slowly on it. The first time down I only went down about three inches and then I stopped. I started stroking his big fat dick with my left hand and putting my mouth around his head. I slowly lowered my mouth down again and this time I went down about half way his massive cock. I stopped there and used my tongue on his shaft and tried to get a breath in. I went down farther another half an inch or so and moaned in ecstasy as his shaft was close to being in my throat. I looked up at Stan and his looked like he couldn’t believe what was happening.
I rose up and looked at him. “Am I your slut, Stan? Am I your cock sucking bitch? Tell me what I am baby.”
Stan got the message and told me “Shut up you fucking whore and suck my cock!”
I was getting so hot I could barely stand it. I honestly felt like a woman with a very wet pussy, I wanted cock so bad, I couldn’t stand it. I took my mouth opened it wide and took at least six inches of his cock in my mouth. I could still feel part of my hand at the base of his cock, so his dick was probably 8 to 9 inches. I shoved my mouth down farther and her Stan gasp.
“Fuck, that feels so good. I have never been blown like that. Take it all!” He said.
I went up for air and moaned as loud as I could as I attacked his huge cock again with my mouth. I took as much as I could and I felt his cock touch the back of my mouth. I slid my mouth sideways and let his cock go down my throat a tiny bit at a time. I kept swallowing and trying not to gag, I was determined to take it all in. I sucked a little bit of air and then I went down a little further and his cock was buried in my mouth. I slowly raised my mouth about two inches got some air and went down again a little faster than last time. I could only imagine what this looked like; I had 8 inches of cock buried in my mouth and wanted the world to see me. I sucked loudly on his cock and raised myself up.
“Don’t stop!” he said as I raised my mouth up and left his cock there. “I am almost ready to cum.”
I motioned him to stay still and I could see he was almost passed out as I got off the couch. He started to doze off as I reached into my bag and brought out an extra long condom, my small dildo and my KY Jelly. I lubed my asshole up thoroughly and came back to the bed. I could see his cock was a little softer than when I left so I started stroking it with my left hand as I put the dildo in my ass with my right. I could feel my ass stretching out as the dildo slipped into my ass. I pulled it out dropped in on the floor and then I whispered in Stan’s ear. “Honey, it’s my time of the month, but I am going to take care of you all right?”
“Sure honey.” He said. But I felt I was losing him to sleep due to all the alcohol
I slipped off my panties and started sucking his cock to get it hard again. I slipped the condom on his cock and then I climbed back and straddled his waist with my back to him. I felt his hard cock and I knew that I had to have it in my ass. The tip of his cock started to push against my asshole as I lowered myself down on the tip of his cock. I held the base of it with my right hand guiding his cock into me. When his cock first entered my ass it felt like my ass was being split in two, but instantly the feeling changed to pure joy.
”Yes” I gasped as I lowered my ass down and took the first inch of his cock in my pussy.
I started to moan as I went further down on his cock and now I could let go of his cock and I couldn’t help but to grab my own cock as I was getting so hard with this big fucking dick now at least two inches deep into my ass. I gently went down a little further and now I had half of his cock in my ass.
“Oh my god.” I gasped again. “Fuck!”
I could feel Stan rising to the occasion. I felt him rise up and gently grab my waist from behind. I looked over my left shoulder to see and he was resting on his elbow, not his back to get some leverage to put his cock in me further. He pulled my waist down gently and another inch of his cock when further into my ass.
“Baby, fuck me.” I moaned. “Please fuck me.”
I was hoping he would not see my cock in front of me, but at this point I was in such ecstasy that I didn’t care. I met his next surge by lowering my ass the same time he was pushing it in and I felt a shot of pain then pleasure as another couple inches went inside me. I raised my ass up and he lowered his hips and then we met each other again and I slid all the way down on his cock and could feel his balls brush up against mine.
“Oh baby, I am cumming.” He yelled.
I had no idea he was so close to cumming as I was in my own private pleasure palace in my mind. I felt him shove his cock all the way up as my ass rested down on him and he bucked his hips up and down causing me to start stroking my cock again.
“Fuck me baby.” I said. “I want to feel you cum deep inside me.”
He shot his load fiercely as he moaned out for at least 20 seconds. When he finished, I slipped my ass off of his cock and I felt like I had just lost a part of me. I couldn’t wait until the next time I had a cock up my ass, because it felt almost as good as fucking a tight wet pussy.
I slipped off the bed gathered my things including the dildo on the floor and went into the bathroom. I was back out in five minutes all dressed and put together. Stan was sound asleep, so I slipped out the door and in two minutes I was in my own hotel room. I stripped off my skirt and panties, took my big dildo out and started fucking my ass with it. It was easy now to take the entire length thanks to Stan breaking me in. I shoved in deeply as I stroked my own cock to an amazing orgasm. It wasn’t as good as the real thing, but it had to do.
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<a href="https://www.lushstories.com/stories/crossdressing/confessions-of-a-sex-crazy-cross-3.aspx">Confessions of a Sex Crazy Cross Dresser Part 5</a>