Cross Dressing Sailor

Let me start by giving you a little background. I have always liked to wear women’s clothing since I was about eighten years old. I used to like to put on my sisters clothes whenever I would be home alone. I liked to wear her panties and when she got older her bras. I would wear her bikinis and strut around the house like a slutty girl. As I got older I would wear my sister’s dresses and skirts. I bought my own panties and stockings.

When I graduated from high school I joined the Navy. When I got to my first boat I wanted to dress like a woman again. We had a three day weekend and I decided to get away and dress up again. I went to St Augustine for the weekend. This was away from base so I would not run into anyone from my boat or squadron. I went to the mall and bought some lingerie, I little black dress, heels, an auburn wig, a Black Hand bag, some makeup and a scarf. Then I got a hotel room.

I went in and shaved my legs, balls and ass. I am lucky as I only had to shave my face about once every three weeks. I have a slim build with a nice small waist. I sat in front of the mirror and began putting on my female face. I added some foundation and blush. I have nice blue eyes and applied eye liner and mascara to bring out the natural blue color. I finished up with some lip liner and lip gloss. I put on the wig and was pleasantly surprised how hot I looked.

I put on my lingerie, a black lacy piece with garters. I rolled on my stockings clipping them with the garters. I then pulled up my black lacy panties taking care to tuck my seven inch cock down. I added the breast enhancers to fill out my bra and slipped on my tight black dress. The dress fit great. It held close to my body and really showed off my figure. The dress fit tight and barely covered my ass and panties. I tied the silk scarf loosely around my neck. I was totally hot looking.

I decided to see if I could pass for a woman and headed out to one of the bars off old town. I notice a lot of heads turn to check me out as I walked from the parking lot. I went into a bar and quickly notice several guys were obviously in the Navy. They were wearing tee shirts with their ships or squadrons name on the front. I was nervous and a bit scared; but I was now committed. I sat down at the bar and a good looking guy came over and bought me a drink. I thanked him. He said his name is Nick and I said I am Amy. We talked for a while and I could not help but think this isn’t right. Nick started to put his hands on my thighs. I excused myself and went to the ladies room.

When I got to the ladies room I checked my makeup as several other women were doing the same. One of them, a cute blonde looked at me and said “you better be careful with Nick”. I asked why, thinking she had the hots for him. She said “he has herpes”. Some of the others agreed with her. I thanked her for the warning. She said her name was Jill and the others were Susan, Jenny and Brenda. I said I am Amy. They asked me if I wanted to go to another club with a nice dance floor. I thanked them and agreed to go with them.

As we walked to the other club we talked about Nick. My female intuition was right. Brenda was walking beside me and touched my arm to get my attention while slowing down. She asked me if I every fooled around with women. She said I was hot and would love to get to know me better. I smiled and blushed a bit. I wanted to pass for a woman; but to get a guy now another woman. I thanked Brenda and said I would think about it. I asked if this was a lesbian club. She said no mostly a college hang out.

We went in and the place was packed. I felt like every head turned as we walked in. We joined the others near the end of the bar. It did not take long for five hot women at the end of the bar to get the attention of most of the men in the club. I had a hot guy about 6’1” come over and ask me to dance. We went out on the dance floor and began dancing. He could move his body. I could see the nice outline of his dick in his tight jeans. It had to be at least eight inches. He was wearing a tight shirt which showed off his nice pecks and six pack abs.

When the song ended the next song was a slow dance. He asked me to stay out and I put my arms on his broad shoulders as he reached for my hips. He held me close and said his name was Chip. I said I am Amy. We talked a little as we danced. I felt his hands move to my ass as he pulled me closer. I could feel his cock press up against my stomach. I laid my head up on his shoulder and breathed in his manly smell. His cologne smelled great mixed with his sweat. I was getting horny and began to fear I might get an erection as the music stopped. Chip followed me back to the girls I came to the club with. Brenda did not look happy Chip was here. Brenda asked me to go the ladies room with her.

Once in the ladies room Brenda gave me a nice passionate kiss. I kissed back before pulling away. I told her I did not think we would work out. The others who were in the ladies room quickly left fearing a cat fight. Brenda looked upset and I quickly told her it is not her fault. She looked at me and I told her she would be very disappointed with me. She asked what I meant. I asked her if she could keep a secret. She said yes. I told her to reach up my dress. She looked confused at my request as she reached up my dress. She quickly pulled her hand back when she found my secret. Brenda said she was sorry I was a man because I really turned her on; but she is strictly lesbian. I asked if she would tell the others or Chip. She said no as we left the ladies room after touching up our makeup.

Chip was still there when we got back. I could tell the way Brenda was smiling she wanted me to get Chip in bed. I flirted with Chip some more while we danced. He asked me if I wanted to take a walk with him. I agreed. We walked out into the park. We stopped under the gazebo and kissed. His lips were nice and smooth. Chip was a great kisser. He ran his hands down my body stopping on my ass. His hands were strong as they cupped and rubbed my ass. I slid my hands down his body to his belt and began to undo his belt. I unbuttoned his jeans as I dropped to my knees. I reached into his pants and freed his throbbing ten inch cut cock. I kissed the head and flicked my tongue over his piss slit while taking in his musky smell. I slid his head through my lips into my eager mouth. I licked around the head of his cock as I began bobbing my head up and down his cock.

I pulled my mouth off his cock and licked his shaft. I moved down to his balls taking care to lick each one. I sucked each one into my mouth as I ran my tongue over it. I then moved back up to his shaft licking my way up one side and down the other side. I slid my lips over the head again taking him back into my mouth. I started t take him deeper in my mouth and I could feel the head of his cock pressing against the opening of my throat. I flattened my tongue and slid him deeper into my throat. I got him all the way down my throat. I pressed my nose into his pubic bush while his balls pressed into my chin. I started to bob my head on his dick faster while I sucked harder. I could tell he was getting closer to the point of no return. I swallowed his whole cock down my throat and held him as the head of his cock swelled. He shot the biggest load I stopped counting as his cock shot twelve spurts of cum down my throat. I needed air and slid my mouth off his cock so is could breath. I got to taste his cum as his cock finally finished its spasms. I licked the last of his cum off his cock. I stood up and Chip thanked me for the best blow job he ever had. We gave each other our phone numbers and walked me back to my car.

I drove back to the hotel with a smile on my face. I had passed myself off as a woman. I got home and jacked off thinking about fooling not only the men but women as well.

I woke up Saturday morning and decided to go shopping for some more clothes. I showered them put on some lace pink panties and a pair of short shorts. The shorts showed off my tight little ass. I put on a pink tee shirt then my makeup. I finished off with my wig. I drove to the mall to see what I could find.

I saw Jill and Brenda from the night before. We talked and shopped together. Most of the talk was about the night before with chip. Jill said he I a very nice guy not stuck on himself like most great looking guys. I told them how we went for a walk in the park and stopped at the gazebo. Brenda asked how far we got. I smiled and told them how far I went. I would have liked to go further but I was afraid Chip would have found out I am not a woman (I did not share the reason with them). Jill asked how well hung chip is I told her ten inches. She gasped saying she had never seen a cock that large. I said it was the first time I had seen or touched one that big also. Jill asked “how much ii was able to take”. I told them the whole thing. Jill asked “how do you get that much cock down your throat”. I said just get it really wet with saliva and relax, then flatten your tongue and as you start to gag swallow.

I found the cutest little pink dress with a slit up the right side and a cute little blue denim skirt. They looked totally hot on me. Jill found the perfect shoes to go with it. Brenda suggested I get a blonde wig to go with it. We had to try six stores to find a hand bag to match the dress. Brenda asked me what I was doing tonight. I said I had no plans. She asked me if I would like to go to a party with her. Jill said “Brenda maybe Amy would like to see Chip or another guy”. Jill told me Brenda is lesbian and thinks every cute girl is as well. Brenda said that she had already tried and was satisfied to know I am not interested in girl-girl. Jill said most of the guys at these parties are gay and the ones who are not are bi.

Jill asked if I would like to go clubbing with her and Susan tonight. I said I would think about it. We exchanged phone numbers so we could coordinate for the evening. I was torn between trying to fool every one at the club again and going for the safer bi and gay guys.

My phone rang, it was Chip. He asked to see me this afternoon. I agreed to meet him at the hotel. Jill teased now you can take him all the way. Neither one of us will be seeing Amy tonight. Brenda laughed and told me to go for it girl, fuck his brains out. She gave me a quick hug and kiss as I left to get ready for my afternoon with Chip.

I hurried to the hotel and changed into my skirt. I touched up my makeup and brushed my teeth to freshen up. Chip got to my room just as I finished. I opened the door. Chip said he had a great time last night and wanted to make sure he saw me today. He said he could not see me tonight because his brother was coming to town tonight. Chip said he really liked the skirt, it showed off my great butt. I blushed as he said this. He leaned in and kissed me. His tongue found its way into my mouth as we embraced. His hands began to explore my body. I did not want him to find out my secret so I stopped him. I said I wanted to take him right now; but I am on my period. I said my breasts are very tender as is my cunt and they hurt to be touched when I am on my period. He seemed to believe this excuse.

I told Chip I could either give him another blow job like last night or if he really wanted to fuck me he could fuck me in the ass. Chip looked shocked by the suggestion; but quickly recovered and asked to fuck me. I said I would be right back and went into the bathroom. I tucked my cock and balls up out of the way. I went back into the room with Chip and took off my panties. I took the tube of K.Y. and lubed up my ass. I then dropped to my knees and undid Chips pants pulling them down to his ankles in one motion. I slid his briefs down freeing his ten inch monster. I kissed the head and began to lick and suck his cock. He was fully erect in no time. I lubed his cock really well. As I stood up and turned away from Chip I guided his huge cock to my tight little man cunt. I slid his cock up and down my crack before placing it over my hole. Chip began to push into me. He pushed three times before the head of his cock pushed through my sphincter. I gasped as he entered me. He held still for me to get used to the large size. When I was ready for more I started to push back. Chip sensed my movement and pushed forward sinking another three inches into me. I felt intense pain for a second and groaned. Chip stopped to let me accommodate his cock. As I relaxed, the pain turned to pleasure. Chip pushed another three inches into me and waited for me to relax again. When I was ready for some more cock I pushed back taking the last of his huge dick into my now full ass.

Chip waited for a moment before he started to pull out of me. He slid out nice and slow then pushed slowly back into me. He gave me several nice long slow strokes before increasing the speed. The pleasure was so intense. He slid over my prostrate with each stroke. I was going nuts. I was also afraid I would blow my load all over my skirt and it would wet through and Chip would learn my secret. I reached a point where I no longer cared. I found myself pushing back harder to meet each thrust of Chip’s huge dick. He was now fucking my ass with everything he had. I could feel his cock deep in my ass. It felt like he was driving his cock into my chest it was so big. I felt him start to swell inside me. Chip asked where I wanted him to cum. I was gone to lust by this time. I just kept pushing back onto his massive dick. I felt his orgasm blast into my insides. Chip must have cum for minutes. When he finally finished he collapsed on top of me. We were both very sweaty and out of breath.

When Chip caught his breath he said he wished his brother were not coming to see him =, he would rather stay with me. I asked where his brother was coming from. Chip said his brother was in the Navy in Georgia and was going to sea soon. I almost chocked when I heard this. I knew my boat was the next to set to sea. He said his brother’s name is Charles but every one called him Chucky. I could not believe it Chips brother is my leading Petty Officer (LPO). Chip said they would be out and he hoped they would run into me. Fear washed over me. I swallowed hard and said I would like very much to meet Chucky. Chip then kissed me and said he had to run to meet his brother.