Brittany's Holiday Encounter

I will start off by saying that I am a 42-year-old married, successful businessman that travels four to five times a year each trip typically last three or four days. And did I say I am a closet cross dresser? I've never ventured out in public- and I don't maintain a dressing stash or keep any clothes at the house. If caught I would most likely lose everything I cherish.

So I limit my cross dressing activities for my business trips. On each of my trips, I start by shopping when I arrive in the city. I shop the high-end stores for my lingerie, and my favorite stockings, which are usually fine quality silk nylons. I guess my fetish for lingerie goes back to days of Sears's catalogs and Sunday fliers with women in gorgeous foundation garments.

This trip would be no different except that it was close to the holidays and cold in the city. I have never been to this city, but as with all my adventures, I do some preliminary research. So I found the location of the nearest mall for shopping, and drug stores for my makeup. On my flight into town I fantasized on how Brittany would be dressed for the week, was she going to be "naughty or nice?" I opted for nice since this was only three days before Christmas. My fantasies while becoming Brittany are getting stronger, it must be that all those hypno-videos are working. I've decided that that I would make my first official public appearance as Brittany. I also fantasized about going to an adult bookstore and sucking my first cock through a gloryhole.

The shopping was fabulous, my cock was erect nearly the whole time, the ladies in the lingerie departments were all extremely helpful, I must say shopping at the holiday time made shopping easier by saying the items were Christmas gifts. I am not sure they all believed me. But the staffs were courteous and more than willing to help. Listening to the holiday music was getting me in the holiday mood and assured me that dressing "nice" would be the right move. The excitement was getting to point it was overwhelming me. My outfit for tomorrow would be a combination of red and white lace bra, red panties, red garter belt, white stockings with small red bows, and a pair of red peep toe, ankle strap, stiletto heels, with the heels longer than my cock. My dress was red with a crisscross top and just covered the tops of my stockings.

I returned to the hotel and laid out clothes for tomorrow on the bed. Just looking at my selection made my cock so hard I had to relieve myself, just as I was ready to cum I stopped, I thought bringing myself to edge might make tomorrow even more exciting. The next day at work was extremely difficult for me during my meetings, I couldn't stop thinking the night's activities and what they might bring. I rushed to the hotel, stopping at the bar I downed two double Tanqueray and tonics and then headed up to the room for my transformation.

I jumped into the tub to relax, I shaved my balls and removed a few stray hairs from my cock. No, I didn't shave my legs, which would have been a dead giveaway to my wife when I got home Christmas eve. The bath was relaxing, I played with my cock with anticipation but was careful not cum. In the tub I attached my red press-on nails, the gin had me totally relaxed. After fixing my nails, I got out of the tub and dried off.

In the bedroom I put on a pair of tan sheer panty hose to hide my hairy legs and to help keep my cock in place. I then put on my garter belt, and slowly pulled up my stockings and attached the garter straps, after fighting with the back straps, I straitened my stockings. Gosh the excitement was driving me nuts, I rubbed my stocking clad legs together increasing my excitement. Next came the panties and bra. I then moved to the bathroom to apply my makeup and brunette wig. Brittany was beginning to take form, I applied a wonderful red lipstick and gloss, I thought to myself Taylor Swift you have nothing on me.

Finally I slipped into my dress and put on my catch-me-fuck me shoes. The transformation was complete, I looked in the full-length mirror and was pleased with my total look- a "nice" respectful girl. Now for the moment of truth, my first adventure outside a hotel room. I would go back to the hotel bar and see if there was any action.

When I went up to the bar the same female bartender was there but she didn't seem to recognize me. I ordered a cosmopolitan and waited for some action. The bartender and I were the only people in the bar. After twenty minutes and two Cosmo's, my, or should I say Brittany's, urges were uncontrollable. I wanted to try a real cock and there was still no one in the bar. The closest adult bookstore was twelve miles away. I decided actually Brittany decided it was time to get in the car and go.

The bookstore had a good rating as far as gloryhole activity. Driving up it was not a seedy location and appeared to be an upscale facility. Walking in I was amazed at the crowd, it was busy hub of activity. I decided to look around the bookstore for DVDs and toys. I found a pair of nipple clamps that had a small chain and bells on them, I thought they would make an outstanding addition to my outfit.

I went back to the theater section, paid my cover charge, and bought the required amount of tokens. Finally a booth opened. Once inside I didn't know which emotion was in control- I was nervous, excited, scared, and horny not knowing what I would do when facing my first real cock. I have been practicing for weeks with my wife's black cock vibrator whether it be sucking it, forcing back gag reflexes or squatting over it and taking a good eight inches up my rectum. Physically I felt that I was ready, in my head I was still fighting with the with the old adage build a thousand bridges and suck one cock and you will always be remembered as a cock sucker. I guess it's time to be known as a cocksucker.

I started the DVD player watching an interracial movie with a tranny sucking and fucking two large black cocks. My cock was straining against my pantyhose. I removed my dress, took off my bra and attached the nipple bell clamps. I loved the joyous noise they made. I noticed some activity in the room next to me, but when I peered through the hole all I could see was a pale white body sporting a small cock resembling a gherkin more than the large monster cock that I had anticipated. I hoped that he would go to the other hole and not the one I was facing, sure enough he must have seen me peering in. He headed in my direction sticking his small cock through the hole.

I guess I could have blocked the hole and hoped something better would come along. Then I got to thinking what if someone rejected me at the gloryhole. After all, I was nice Brittany, I might as well give this cock a thrill. Now it was time fish or cut bait. I have fantasized about sucking cock for over a year and now I have this opportunity, take it or walk away. I thought if I don't do it now I will never know what a strange cock would taste like. As it came through the hole, I began to kiss the small head, and lick the shaft if you could call it a shaft. I easily took the entire cock in my mouth, as it stiffened it did improve in size to a near average cock. I remembered that humming was a sensation that I enjoyed once when my wife sucked my cock and since holiday's carols filled my head, I started humming "Santa Claus is Coming to Town" on the strangers' cock. Before I even finished with the first verse his cock exploded in my mouth with more cum than I thought was possible. I swallowed hard and repeatedly. I did manage to capture all the cum. As I started re-sucking the cock it suddenly pulled out, the light went out in the cubical, and he was gone.

As I was reapplying my lipstick and sitting there in my stockings and panties I was thinking to myself it's not gay if you are dressed as girl and wearing lipstick and stockings "right?" Before I could collect my thoughts, the light reappeared. Looking in I gasped, it was that 9 or 10- inch black cock I had wished for, I didn't have a measuring tape but it didn't matter, it was the largest and blackest cock I have ever seen. It started to come through the hole, I took a deep breath, thinking to myself that this was my good karma for sucking the smaller cock.

I kissed the crown as it approached, I flicked the tip gently, my tongue moving slowly around the head. Then slowly I started taking the cock into my mouth. The cock was so huge I didn't know how I was to going to be able to suck it. I slid my tongue up and down the sides repeatedly. I could almost take his pulse by the blood pumping through the huge veins. Now that his cock was moist with my saliva I tried to swallow it whole, I must have been down about four inches when I was starting to gag. Remembering a video I had seen on line about putting your left thumb into your fist and squeeze tightly it would help stop the gagging reflex, unbelievably it works- I was able to push my head down deeper and relax my throat enough that I could feel the base of his cock butting up against my nose.

As I continued, he said very few women have ever been able to deep throat him. As with the other cock, I started humming, this time it was Jingle Bells and I swear my nipple clamps were ringing to the beat. He asked if he could join me in the booth, that he wanted to be able to see me suck his cock. I knew I shouldn't but I was thoroughly enjoying the thought of pleasing such a cock. I didn't want to release his cock from my mouth but I did just long enough to unbolt the door to the cubical.

He was a giant compared to me, somewhere about 6'5" I guessed. Once in the cubical, he dropped his pants and his cock sprang back to life, I was there on my knees making passionate love to a huge black man with my mouth, staring up in to his face, he smiled back at me. He started a more forceful rhythm, grabbing the back of my head he was pounding away and this was starting not to be as much fun. Just then I felt the presence of another person in the cubical. He left the door open and someone else was in there with us. I felt another cock beating me in the face as to say it wanted attention. Just then the cock in my mouth was starting to throb, I felt the cum beginning to surge and it hit with a strong force in the back of my throat, the man pulled out of my mouth and another large stream of warm cum hit me in the face. I turned to the other cock, it was smaller and thinner than the other one, but I happily took it in my eager mouth. I was working this one harder and faster- I wanted to finish it off quickly and be done, my jaws were beginning to ache.

The person's whose cock I had just sucked, moved behind me and pulled my panties aside, I tried to cry out but it was impossible with the cock in my throat and hands against my head. I felt the cool sensation of something being applied to my asshole, it must have been lubricant, I felt a strong pressure on my back side, and I knew the pain I was feeling was from another cock. It pressed deeply inside me, tears were running down my face, I wanted to fight back but I couldn't. His thrusts were creating a new pressure sensation on my prostrate, I couldn't help myself, I could feel my cum dribbling out my cock and into my panties. After a few minutes of steady pounding, I felt another strange sensation in my ass the man began cumming in my ass. Laughing the man with his cock in my mouth pulled out shooting a long warm slick wad of cum near my eye that slowly slid down the side of my face. The man in my ass pulled out also, as he started to stand he reached down and grabbed my purse, coat and dress and both men ran out of the cubical down toward the entrance.

Without thinking I got to my feet as fast as I could and tried to run down the hall. The high heels made running impossible. I quickly took them off and kept them in my left hand as I headed toward the front of the shop. I yelled for someone to stop them but it was too late they were already gone. So here I was standing in an adult bookstore, I must have look ridiculous standing there in my garter, nylons, panties, high heels in hand, a face full of cum, more cum running down my legs and a pair of bells clamped to my nipples. I mustered as much dignity as I could muster and walked back down to the cubical to see if I could find my car keys. Fortunately my keys were there on the ground.

I headed back out to the front, which had cleared out. The proprietor informed me that he called the police for me and they would be here in about ten minutes to take a report. I looked around for something to wear or to cover me up but there was really nothing, I walked out to the car and got in and started the engine. I just sat there and started to cry. How was I going to get back in the hotel looking like I did, what was I going to tell the police, would they arrest me for lewd behavior? What would I tell my wife if she found out? I decided to leave the area, I didn't want to talk to the police. After all, they had only gotten away with a dress that I was going throw away and a few dollars. I had left all my identification, hotel key, and credit cards in the car. I decided I would drive to the hotel and wait until activity quieted down and try to sneak in a side door and hope that no one sees me.

I was just getting on the freeway ramp when I felt the right rear tire blow. I got out to assess the damage. The tire was completely flat so I couldn't drive on it, I would have to change it. Great, what else could go wrong this evening? I opened the trunk got out the jack and spare. At least the ramp was somewhat secluded and not much traffic. As I started to change the tire, here came a set of headlights, I couldn't make out the car as it pulled close. I prayed it wasn't the police. I thought to myself this is all I need. I heard the car door open and because of the light I could not make out the figure approaching. I just froze trying to cover myself with the spare tire.

The stranger handed me a box and said, "Merry Christmas, I thought you could use this!" I just looked down at beautifully wrapped package.

"Open it," he said as he turned away.

Inside the box was a pair of gray sweats, in my size.

I said, "thank you," as he started walking away. He didn't respond, however, I could distinctly hear him humming "Santa Claus is Coming to Town."

As he drove off I tried to see what the man looked like, but it was too dark and the headlights were too bright. All I could determine was that he was driving a red car, a make that I had never seen before. As it drove past me I saw his vanity plates "PRANCER".