I had been at sea about a month when my ship pulled into Naples, Italy. The only action I had seen had been slipping away to my hiding place on the ship to jack my dick on a regular basis. I was ready to find some Italian pussy.
I was slim about 6' with blonde hair and a fat 7" cock that would get hard when the wind blew. I was eighteen and from the south. Somehow I knew the small town I was from wasn't for me so I joined the navy and found myself overseas.
Anyway I got some leave, about four days worth, in Naples. I started out drinking with some of my friends. Steve this horndog I knew, who was always talking about scoring some pussy, said that the whores could be found by the castle in the middle of town. The castle was unmistakable, in fact you could see from where the ship was docked. Not wanting to admit I was hard up enough to pay for pussy, I let them go there separate ways. I continued to drink hoping for some luck with the local women.
Since I was on leave I was able to remain ashore when most of the sailors had to return to the ship. I waited until late in the evening and that was when I made my move to the castle. I sat on a bench outside the castle for awhile watching the whores come and go. When the most beautiful Italian woman with long black hair and dark complexion came sauntering up to me. She said "hi sexy are you looking for a date." She was incredible. I was horny so I said yes. She told me her name was Alexandra. She hailed a cab and we were off to her place.
While in the cab Alexandra placed her hand on my erect dick and a sly smile came to her lips. She then leaned over and we kissed a long hot sloppy kiss. She asked me how long I would be in Naples. I told her I had four days leave. Then Alexandra told me the night was on the house because she was finished working so I was just for fun.
The thought of fucking this beautiful woman made my hard dick become stone and the rest of the cab ride was very uncomfortable. When we got to Alexandra's place I paid the cab driver and as he pulled off I felt her hands on my cock. She rubbed my dick through my pants. Then right out in front of her house she went to her knees and undid my pants. Alexandra then pulled out my erection.
She looked me in the eyes and asked if I wanted her to suck my huge cock. I was nervous about being in public but you don't say no to a beautiful women on her knees with your cock in her hand. I said, " please suck my hard cock." She licked and teased the head with her tongue before working down the shaft to my balls. Alexandra sucked my balls, then with one quick motion engulfed my entire 7" cock. I almost came right then but she sensed I was too hot and backed off.
She stood up and smiled. This bitch was hot. She then led me into the house and offered me a shot of some clear black licorice tasting liquor. I downed it and she poured another. Then Alexandra told me to help my self and to get comfortable. She then went and took a shower. Leaving me horny and nervous. I had a couple of shots before she returned in a tight robe that showed her body, especially her large tits. My head was spinning from the drinks but I still had my hardon.
Alexandra was mad at me. She ordered me to strip, which I quickly did because I didn't want to screw up my chance to get laid. Then she ordered me to stand with my feet apart. I did what she told me to do and the smile returned to her face. Alexandra then took my cock in her hand and began to stroke it with her other hand she began to rub my ass. She started saying things like "Baby has a big cock, its so hard, I bet you want me to suck your fat hard cock, I bet you would like to fuck my tight asshole."
Then she bent over and took my dick into her hot mouth. I reach her tits and began to rub them. Alexandra began to deepthroat my cock. With her hand she began to work a finger into my tight asshole. I grabbed her head and face fucked her, shoving my dick all the way down her hot throat until my balls were on her chin. Then I pulled completely out. I plunged my dick in to the base again and began stroking this bitch's mouth. I worked until my balls began to tighten and I was ready to cum. I pick up my pace and soon I was cumming.
Alexandra took everything I had and continued to suck on my cock until my spasms subsided. Before I realized what she was doing Alexandra was up and kissing me. She shared my cum with me and I had no choice but to take my load and swapping between us.
I backed off and she said "fuck that was good did you enjoy get your cock suck and fucking my face." I said "your hot, I want to eat your hot pussy." She stood and I knelt. Alexandra looked down at me and smiled a cum soaked smile and opened her robe.
Hanging just inches from my face was the biggest cock I had ever seen. Alexandra was a man, no she had huge tits, but she had a ten-inch cock. I didn't know what to do. I wanted to run but part of me reminded me of how good it felt when she was sucking my dick. Alexandra grabbed my chin in one hand and her cock in the other and put the head to my lips. She said "please honey suck my dick, I need to get off, I got you off, now it's your turn." I stopped thinking and opened my mouth. Alexandra's cock entered my mouth and just like that I was cocksucker. It was strange the image in mind of this huge cock growing hard in my mouth and then to open my eyes and see it and feel it on my tongue. My dick got hard again.
Alexandra sensed my change in attitude and began to encourage me. She said " that's lick that cock make me hard baby." Her dick grew and became hard in my mouth. I tried but couldn't handle all of it. Alexandra told me to take as much of her cock as I could. I gagged and had to back off. She smiled at me and said "my sexy cocksucker, your doing so good I want you to fuck my tight ass." I was thrilled at the thought of pumping Alexandra's hot ass full of my cum but I wanted to suck her cock some more first. I worked my tongue and the head and lap up the precum dripping like it was some salty life giving elixir. I pumped her cock as I sucked the head. Alexandra moaned and started face fucking me slowly at first. Then she grabbed my head and pulled me off her cock. She said she wanted to save her orgasm for something special she had in mind for me.
I stood. Alexandra lubed my cock and bent over placing her hands on the coffee table, exposing her ass for me to fuck. She looked incredible bent over with her cock hanging between her legs and that tight hot asshole begging for my hard dick. I push the head of my cock into her hole and she moaned. Her ass muscles gripped my cock like a vice but I continued to pry her open as I inched my fat dick farther in until I was up to my balls in her ass. I then inched out slowly until I was completely out. I forced my cock back into her closing asshole and she moaned and begged me to fuck her harder. I plunged to the hilt quickly the next time and began to pound her hot ass.
Alexandra began to mutter in Italian. I couldn't understand but I was sure she didn't want me to stop. Soon we were fucking at a frenzied pace and I couldn't hold out any longer. I dumped a huge load of cum deep in Alexandra's guts.
I pulled out and started to rest but Alexandra began to lick my spent cock and her finger found my asshole. First she inserted one finger and then another. Soon she was fucking my ass with three fingers and sucking reviving cock. This was new to me I had never had any girl play with my asshole before and it felt great.
Alexandra then told me she wanted to fuck me with her huge cock. I asked her to be gentle. Then Alexandra bent me over the table slowly worked her monster cockhead into my virgin asshole. I thought I was going to die from the pain and begged her to stop. She paused for a moment and began her assault on my asshole anew. Soon she was working in and out of my ass steadily.
The pain eased and Alexandra fucked me harder. As she fucked me Alexandra leaned over and said, "How does my cock feel up your hot ass. You sailors are all the same. You say you want pussy but when I reveal my fat cock you're on your knees sucking it and begging me to fuck your hot navy ass. Say it, you fuck slut, tell me what you want."
I was having the best sex ever and knew I would do whatever she wanted. I pleaded "please, fuck me harder with that big Italian sausage. Fuck my hot ass and then I want to taste your cum." Alexandra stroked my well-worked ass for a few more minutes and pulled out. I licked her nasty cock until she blasted my face with her wad.
Alexandra looked down and my cum soaked face licking her cock and asked, "did you like getting fucked and sucking my cock." I smiled and continued to suck her cock.
We had sex again that night and she fucked my ass until I came. I found out I like sucking cock and loved the taste of cum. We fell asleep in each other's arms.
I awoke the next day hungover and alone. There was a note on the mirror that said "You were a great little cocksucker last night. I left you something to wear. You will wear what I left! Go to the hotel and get your things. I have a surprise for you but you must do as I say. I have another copy." I didn't know what she was talking about until I found a lacey bra and panty set. There was a sexy red dress and a blonde wig for me. Next to the things I found a videotape. I played the tape and found it was of Alexandra and me having sex. She was blackmailing me I had no choice.
I went into the bathroom and found a razor and shaved as close as possible and put on makeup I found on the counter. Then I dressed stuffing my bra with tissue. Finally I put on the wig and was surprised at how passable I was. I was actually cute. My cock began to grow in my black lacey panties. I was scared as hell when the cab arrived to take me to the hotel.
I entered the hotel and made my way to my room as gracefully as possible. Nobody paid me much attention except two sailors I didn't know whistled and checked me out. My cock became harder and I'm sure it showed a bulge in the front of the tight red dress. But I managed to make it to my room.
I opened the door to find a young dark handsome Italian sitting on my bed. He smiled and said that Alexandra had sent him to give me the other copy of the tape. I thanked him. He said he had watched the tape and I must suck his cock for his silence.
I closed the door and started to take off my wig when he stopped me and told me he wanted a blowjob from a sexy blonde slut. I went to my knees and reached to open his pants. I undid his pants and pulled out a massive 11-inch cock that I had to hold with two hands.
I jacked his growing dick and lick his balls. Then I work my way up to the head and twirled my tongue around it. I took his cock into my mouth and sucked it. I certainly was a long ways from my small town home there on my knees dressed like a woman sucking on this massive young mans cock. I realized I was a cock sucking cum loving slut and this thought turned me on and I began to really suck and lick his cock with abandon. He moaned and cursed "suck my big manmeat you whore. You bitch your going to make me cum." With that his massive fire hose let loose and he unloaded into my hot lipsticked mouth. When he finished he stood up and put his dick away. He tossed me the video tape and left me there on my knees licking the cum off my fingers.
I gathered my composure and my things and left the room. When I returned to Alexandra's she wasn't there but a friend was. She said her name was Anna and I looked adorable.
Anna was smaller than Alexandra with short black hair and pert little tits. She looked to be 17 and Anna was hot. I was still in my red dress but I wanted to change badly because this sexy little nymph made me feel like a man. I then had a thought did Anna have a cock like Alexandra. That made my cock harden in my panties.
Anna offered me a drink and told me Alexandra would be in and out most of the day with customers and we were to stay out of the way unless she ask for us. She then led me to her room.
Anna then kissed me while her hand found my growing cock. We kissed as she rubbed my hardness through the dress. My hand went to her crotch to find a big dick waiting for me there. I was a happy sailor. Anna stepped out of her dress and I removed mine. She had on only black garters and a nightie. I removed my bra. Anna pulled my cock from my panties and took it into her mouth.
She looked like a little girl with a lollipop. Anna sucked cock like a pro and she loved it. I worked my way around so could suck her big dick while blew me. We suck each other in a 69 for a while until she came in my mouth. Her cum was delicious. I told I wanted to fuck her cute tight ass. She giggled and rolled over.
I spit on her asshole and worked my finger into Anna's sweet young ass. I removed my finger and shoved my hard cock into that teen shemale's awaiting asshole. She grunted and squirmed but loved every minute of it. I long stroked her tight shithole until she squealed in delight.
Just then Alexandra came in and from where she had been watching and shoved her hard cock in my face. I sucked that fat cock and fucked Anna like a stud. Alexandra said, " suck my cock you bitch and fuck her ass." That was more than I could stand I blew my load into Anna sweet young ass.
Alexandra was getting close but had a customer waiting so she didn't want to cum yet. She told Anna and me to get dressed and come play with her new friend.
I put the red dress back on and Anna helped me fix my makeup and we went into the main room. I was shocked to see Alexandra sitting on the couch with my friend Steve on her lap riding her fat cock. Steve the smug asshole who was so gun-ho about getting some pussy was taking it up the ass.
Alexandra noticed we had entered the room and she paused from fucking Steve to introduce us. She said my name was Nikki and I liked to suck cock. Steve said hi and look puzzled. Alexandra introduced Steve as her cock-sucking bitch he smiled uncomfortably with her huge cock buried to the hilt up his ass.
Anna walked over and went down on Steve's cock. I joined her and we took turn sucking his 7" cock. After a few minutes I stood and pulled up the front of my dress and offered my unsuspecting friend my hard dick. Which he readily took to licking and jacking.
Alexandra continued to fuck his ass while Steve sucked my cock. Anna sucked on Steve until He couldn't take it any longer and came in her mouth. I wanted to fuck my navy pal's hot ass so I suggested Alexandra and I switch. She consented and soon my fat navy cock was fucking Steve's unsuspecting asshole. Steve took turns sucking on beautiful Alexandra's cock and hot Anna's cock.
Alexandra came first all over his face. She was followed by Anna dumping her hot load on Steve's lips. This drove me to a frenzied pace and Just as I was cumming I ripped my wig and called for Steve to look at me. The look of fear and realization on Steve's cum soaked face caused me to blast off into his hot fucking ass.
I said to Steve I can't believe your are such good piece of ass and quite the cocksucker. Steve realized we were both in the same trouble if anyone found out, relaxed and wiggled his ass on my spent cock. We all had a good laugh and a few drinks. Steve and I became best friends over the next few days.