A Trip to Remember Ch. 04

I made some weak statement about changing my clothes but she would have none of that. During her earlier search of my room she came across my two purses and she told me that I should pick one to maintain the proper illusion.

I chose my red fake Louis Vuitton purse and Judy exclaimed "That purse actually has style."

I certainly agreed. How can you go wrong with a fake Louis Vuitton? I had crossed a lot of lines today and I was about to cross another. I put a minimal amount of items in my purse and we left the room.

I wanted to go down the steps but Judy insisted that we use the elevator. I stood next to Judy looking at my reflection in the elevator. My hair looked fine, my blouse was tucked into my skirt and my face was made up decently. My fake tits gave me a respectable figure.

The handles of handbag were at the crook of my elbow. I thought this the most glamorous and feminine way to carry a purse. In the elevator I realized that I could make the look more feminine by bending my wrist, so I did. We rode the elevator down and it opened on the main floor. I would have liked to have gone to the ground floor but Judy was making a point.

People were everywhere and the room was lit as if it were day. Judy gave my elbow a shove and we walked out of the elevator together. We oriented ourselves, or I should say Judy oriented herself and I was just looking around to see if anyone was pointing at me. No one was.

I stopped hyperventilating and Judy pointed our way to the proper stairs. We walked down the stairs, me being careful to hang on to the banister rail, ever aware of my heels. We made it to the ground floor and exited the proper door and we were off once again down the River Walk. This time my heels were clicking on the asphalt and I could feel the cool air up my legs to my panties. My purse was at my elbow, my wrist was bent and I allowed my arm to swing slightly to the left and right as we walked. I was ever so feminine.

Our walk was reasonably uneventful. Two men started walking with us but Judy was able to discourage them from giving us any further attention by telling them that we were lesbians and not interested in them. They made some comment about being able to turn us but we walked on.

Through the whole walk I was thinking that I would have to do the walk alone back to the hotel. At Judy's insistence we stopped in at a bar and had a drink, appeltini's again, they were quite good. Thankfully no one hit on us.

We left the bar and finally reached her hotel. Judy was saying goodbye and I told her that she was forgetting something. "Oh, I don't think so" she said. I pointed out that she hadn't given me back the key for my chastity. Her answer was "Oh that's right. Give me your telephone number so I can text you." We exchanged numbers and she then said "I'll see you tomorrow." Off she went with my desired key, into her hotel. I tried to follow her but she was quickly lost in the humanity.

I made my way uneventfully back to my hotel. When I got to my room I was exhausted. I still hadn't cum and I couldn't get my chastity off but at least the safe was open. I went to the safe and discovered it was locked. I knew it had been open because Judy had my chastity key.

I texted Judy:

To Judy:

Judy safe is locked. Did you lock it again? What is combination?

The reply:

To me and one other:

"The slut is back up in room 705. She says that she needs her safe unlocked. Do you think you have the time or are you too busy?"

I received a second message soon after:

"I am a busy man and would need to be convinced that opening the safe is worth my effort."

This time I didn't need any convincing. I had given this man a blowjob and discovered that sucking on a real penis was more fun than sucking on a store bought plastic one. I was prepared to blow him again.

I also knew that sucking on a real cock wasn't the only thing that I was interested in. I felt like a high school girl going to her prom knowing beforehand that she was would be "going all the way."

I fixed up my makeup and made other preparations and then texted back:

"Come and get it. Open my safe and I will suck you dry. Knock twice and I will let you in. Hurry, this bitch can't wait to service your penis."

In short order I received two replies:

From the hotel employee "I am on my way."

And from Judy:

"Why you horny little sissy tramp."

I was a tramp and I was going to prove it. This time I didn't use my blindfold. I wasn't going to be coy, I was on a mission. I was going to suck some guy's penis while I looked directly at his face and then I wanted him to stick that same penis up my ass pussy and let him pound me until he ejaculated. I was looking forward to it.

I soon heard knocks and I opened the door. He was taller than me, even though I was still wearing heels. He was good looking enough and he seemed shocked that I was alone and he seemed apprehensive.

He stammered something and looked around and asked if the other woman was around. I told him that I was alone and that I was pleased that he had come to help me. He stood outside the door, unsure of what to do and then I realized our dynamics had changed. I was the one wearing a skirt and heels and had boobs pressed against my semi-sheer blouse. I was the one who was going to be used sexually and yet these were all my decisions and I was controlling the situation. I told him to come in and take care of my safe and then I would take care of him. He smiled and then awkwardly stepped around me.

A short time later the safe was open and I told him to take off his shoes and to come to the middle of the room. He did as I requested and I then moved in front of him and dropped to my knees. I loosened his belt and unzipped his zipper and finally unbuttoned his pants. I lowered his pants slowly moving my hands down his thighs looking up at his face the entire time. I saw him inhale briskly as the sensations began to overload his senses.

I had him step out of his pants and then spread his feet apart and my hands now moved up his inner thighs until my hands met at the base of his crotch. My one hand then gently cupped his testicles as my other hand felt his hard throbbing penis through his thin cotton briefs. I looked up at his face and I could see that his breath had accelerated.

I refocused on the job at hand. I carefully and slowly pulled his briefs down as I gazed into his eyes.

He stepped out of his shorts and I again slowly ran my hands up the inside of his legs. One hand gently held his balls as my other hand slid up his erect penis. When my hand finally reached the tip of his cock I bent his member towards my face and licked the tip of his cock to lubricate it. I then slowly circled the head of his cock with my finger while I ran my tongue along the sensitive nerve of his penis from the base of his tool all the way to the head of his cock. I then directed the head of his penis towards my face and ever so slowly opened my mouth to accept his swollen member.

I encircled his penis with my painted lips and slowly accepted more and more of his cock into my mouth. I knew that I could deep throat him and I was determined to do so. My mouth saliva provided the lubrication necessary to entertain his tool.

My mouth disengaged and I looked up at his face. He looked ecstatic and I knew that he was approaching orgasm and I needed to slow him down. I took a condom that I had previously unwrapped and slid it over the head of his penis and then down to the base of his cock. He moaned saying "Oh god, please don't stop." I had every intention of stopping.

I released his cock from my mouth and took some lubricant and rubbed it over his penis and then told him to follow me to the bed.

I knelt at the edge of the bed and laid my body face down on the bed. I pulled up my skirt and as discretely as possible I removed the lubricated anal plug that I had inserted into my ass before he came to my room. Its removal was made easier because I was wearing crotch less panties and I was wearing them backwards. By doing so my ass was more easily accessed and my imprisoned cock was covered with the maximum amount of material afforded by the thin pink panties.

I said "Come over here and finish me off. I want to feel your big strong penis in my ass pussy."

I didn't see it but I think he ran to me. He mentioned how sexy my panties were and then he proceeded to push his penis into my pussy. The entrance was easy because my ass had been abused numerous times today finally being stretched by my anal plug.

He began to pound my ass. I knew that he wouldn't last long because he was already close to coming when I was on my knees blowing him. He was grunting and groaning and telling me that I had a "real tight pussy."

I told him that it should be tight since he was the first man to ever fuck me. He then drove hard into me and his penis pulsated as he came in my ass. He finally collapsed down atop me.

When his penis deflated he slowly got off me. I stood up brushing down my clothes and making myself as respectable as possible. I expected him to remove his condom but he didn't. He just put on his briefs, then his pants and sat down on the chair and put on his shoes.

He then said "That was nice. Uh, we need to do this again. Uh, well I guess I better go. It was good seeing you again. Thanks for everything." He then headed out the door.

Thanks for everything. He made it sound like I bought him lunch or something. For god sakes I probably gave him the best blowjob he ever had and maybe the best fuck he ever had and he says "Thanks for everything." Sheesh, some men.

Well I had spent a day sexually satisfying a woman and a man giving the man two blowjobs and letting him fuck me and I was still sexually unsatisfied. My penis was still locked up and I was horny and I wasn't sure when I was going to get the key to release my imprisoned cock.

I was thinking of again assaulting my ass with a dildo, knowing that I could release my sperm if I properly milked my prostate. I also knew that while I would release the fluid, I would not receive the normal pleasure of sexual release. I would still be horny.

I then got a text to me from Judy saying I should meet her at her hotel tomorrow at 5 PM and we would go out for dinner at a CD restaurant and then go later to a lesbian bar. I was told that I should dress "Slutty".

To remove the lock on my penis I had two choices, get to a hardware store and purchase some kind of cutting tool and cut off and ruin my chastity device; or dress slutty and look forward to another night of debauchery. I started choosing my clothes for tomorrow.