My Quest for the Ultimate Sexual Goal - Something New

I packed all I could carry into a large wheeled holdall and grabbed my phone and charges and walked to the door. Mum never said a word. Dad hugged me and slipped some money into my hand. I will phone you he whispered, take care Samantha, I will always love you. I love you too dad I said and left the house for ever.

I went to the station and boarded a train for the city. I didn't know what I was going to do or where I would sleep. I took the money dad had given me out of my jacket pocket £300. I welled up and silently thanked him.
There was a guy sat opposite me and he asked me if I was OK? Fine I replied wiping a tear from my cheek. I have just left home, long story I said and now I have to find a job and some where to stay.
I might be able to help you he said. My name is Giles and I have a two bedroom apartment in the city where I live with my wife, no kids.
My heart sank because he was so hot.
My name is Samantha I replied but I don't want to trouble you and your wife.
He took his phone out and rang her.
Hi baby he said, I am bringing a friend Sam home for a few days. No, gorgeous and very cute. He hung up, settled then you have a bed for the night.
Thank you so much Giles, I am so grateful. We chatted about our lives in general. He was the manager of several fashion stores and visited them each week. I told him that I had just left school, I had actually been excluded for fighting.
We arrived at our destination and Giles offered to take my bag off the train. He hailed a taxi and we were soon at his apartment.
He lived on the 10th floor.
We went in and he shouted I'm home babe as we went into the lounge.
A door opened and a naked guy walked in. He had a wonderful uncut cock that swayed when he walked. His body was totally devoid of hair apart from his eye lashes. They did a long passionate kiss. Fuck, trust me to get the gay guys.
When they finally came up for air, Giles introduced me to Jenson. This is Samantha, Sam for short babe. Jenson walked over to me and I held my hand out. He put his hand up my skirt and ran his fingers over my crotch. You're no good to me love he said, no cock and balls. He kissed my cheek and went back to Giles.
Sam let me show you your room Giles said. And keep your hands off him bitch Jenson said. I held my hands up and then followed Giles into the bedroom.
There was a window running the full length of one side. The view was spectacular, the city below and the hills in the distance.
Make yourself at home Giles said. I noticed four pairs of handcuffs attached to the head and foot boards of the bed. They're for when Jenson is out of control, I chain him up and let him calm down.
He left me to unpack and when I had finished I returned to the lounge were Giles was also naked, sat on the sofa with Jenson sucking his wonderful cock.
I got a tingle in my pussy.
Jenson was lying on his side, his semi hard cock dangling over his thigh while he dealt with Giles. I knew I shouldn't but I had to, so I knelt down and took Jenson's large cock in my mouth.
Jenson tried to get up but Giles seeing what I was doing pushed Jenson's head further onto his cock leaving me to enjoy Jenson's now expanding cock.
I bobbed my head until he was touching my throat. I needed to make Jenson like me so I took a deep breath and forced my mouth down his cock. I felt it go into my throat and his balls touch my chin.
I didn't panic and lifted my head slightly and then back down. I slowly moved further up his cock until I was sliding its the full length in and out of my throat.
Fucking hell Gavin said , letting go of Jenson's head and moving to see what I was doing.
Get the bitch of me Jenson cried, I don't want her dirty fucking mouth anywhere near my cock.
Have you seen what she is doing to it Giles said? Jenson opened his eyes and shouted she is fucking swallowing it all. Nobody has ever done that to me before.
Two more downward strokes and Jenson unloaded his balls into my mouth and throat.
He was moaning and saying thing like he had lost his virginity to a whore. Shut up you drama queen Giles said. I would love Sam to do me like that.
OK I said, sit on that chair. Giles did and I did the same to him. He was more difficult because his cock was fatter and slightly longer.
After Giles had cum and I mean cum he asked if there was anything he could do for me? Food would be nice I said. Weirdo Jenson said but hugged me. How can you be hungry after two loads of protein he said? I am a growing girl I said.
Why don't you show us what you're got then I will order pizza Giles said?
You mean take my clothes off I replied? Yes Giles said, you have seen us two naked and tasted us Jenson said and without my permission too. You loved Giles said and slapped Jenson's ass playfully.
OK I replied and I slowly removed all my clothes. They watched in silence like the y had never seen a girl strip off before. I stood with my hands on my hips and my head slightly cocked to one side.

Jenson was the first to move. He stood up and came over to me and grabbed my boobs. Giles darling I want these he squealed they are perfect and started kissing and licking them.
What size are they Giles asked as though he could just buy them? 34C I replied why? Jenson wants to have a boob job and has been looking for the perfect breasts for ages.
Thank you sweet I said and kissed him. Don't do that he might enjoy it Giles said.
Giles ordered pizza and even went to the stark naked to pay for it.
Has we ate we chatted about our lives and ambitions.
Giles ran a chain of boutiques catering mainly for men who like dress up as women. He said the garments were of larger sizes and he could get customers designs made up. We can supply any female garments to fit males. We even help when a client has breast augmentations. Like chicks with dicks I said?
I wish you were a chick with a dick and then this, pointing to his splendid cock would go right up your arse Jenson interrupted. Any time you like big I replied even though I had never had anal sex.
What about you Jenson I asked?
My family disowned me when I came out so I worked as a male prostitute. I found Giles, he proposed and we have lived together 6 years.
Now you Giles said.
I have been interested in sex since we did biology at school. Some boys were rude and would flash there cocks under the desks in class. I thought it would be fun to do it too so I would take my knickers off and sit with my skirt pulled up and my legs wide open. I got caught and was expelled so I would walk around town watching men and women kiss, dogs fuck or during bad weather watch my dad's porn stash. Some of the things they did in those films looked impossible but since I lost my cherry to my dad I want the greatest sexual experience ever.
So what do you think that will be Giles asked? I don't know until it happens I said. I did enjoy your cocks though. That's the first time I have ever got one down my throat.
God that's the first time I have ever been number one Jenson said and clapped his hands together.

Right Giles said shall we go out for a drink? Great Jenson said you know how long it takes me to get ready so I will be staying in.
I could help you with your make up. It might be below your high standards but I can make you look feminine.
How the hell can a sex maniac school girl make me look gorgeous?
The least you can do is let her try Giles said.
Jenson and I went into their bedroom and I said put your makeup on and then I can see the problems if there are any.
I think I know how to apply makeup lady he said so I sat on the bed and watched as he spread the makeup on.

After 20 minutes he pulled on a blonde wig and turned around. I did my best not to laugh; he looked like a drag queen. Come with me I said and we went to see Gavin.
Jenni you look lovely Gavin said as I stood behind her pulling faces and putting my hand over my mouth pretending to laugh.
Come on Jenni the drag queen take all that shit off your face and I will transform you.
You cheeky bastard Jenson screamed, I was going makeup before you were even born so don't tell me how to do it.
Fine go out looking like 6 to fucking gargoyle then. He lunged at me but Gavin grabbed him.
I'm going to kill that fucking bitch he screamed.

Baby let Sam have a go and if you don't like it you can do it again your own way. I'm still going to fucking kill her he said and went into the bathroom.
He came back and I said what a fantastic blank canvas. Piss off Jenson said. I walked to him and squeezed one of his arse cheeks and said I think you are a kissed him on the lips. Grabbing his cock I led him into the bedroom.
I turned the chair around so Jenson could not look in the mirror as I turned him into a woman.
He sat down and put the makeup on the table behind him. We were still naked and when I straddled his legs he said don't put your cunt anywhere near me.
Shut up and let me do my magic I replied.
I sat on facing him and I rubbed my pussy on his cock. I took his hands and placed them on my butt. Do not remove them from there or I will bash you.
I took a very long look at his facial features and said I think slightly Oriental.

I started with a light foundation, brushing away from his nose. Then I applied a pale straw colour which was my base for the rest of the makeup.
I pencilled his eyebrows on quite thin with a gentle up curve that the outer ends. I applied a very thin black line under the eyes and short stroke of black to make them look a slight almond shape. A very pale shade of pink was put on his eyelids and because he had wonderfully long eyelashes I applied mascara so they fanned out. I applied lip gloss with my finger so that the features of his lips were visible. I didn’t want the Geisha Girl look.
A short black wig in the style of a bob completed the look.
I got off his lap and Jenson said you have dribbled on me. That's because you look sexy. I sat on the bed waiting for him to look in the mirror.
Jenson turned round and gasped. What have you done you bitch, I look like a real woman. So you like it then I said? Yes, his voice trembling with joy. Don't you fucking dare cry I said because you will ruin it.
He hugged me then put his hand on my pussy and said all I need now is one of these and slowly inserted his middle finger into me. I kissed him and grabbed his cock. Jenni will you fuck me later, you can pretend you're a woman with a strap on. We'll see he said.
Let’s go and show Gavin I said. You wait here and I will call you.

I went to the lounge and stood behind Gavin and covered his eyes with my hands.
OK Jenni I shouted and out of the bedroom she emerged.
I uncovered Gavin's eyes and he let out a low whistle. Jesus that is fantastic, what a transformation, they kissed and then Gavin hugged me and said thank you for that.

We dressed, wore a pink strapless dress and heels, no underwear because I intended to get fucked several times at least.
Each person we talked to I was introduced as Jenni's sister.
In one bar a tall black guy asked if he could buy me a drink. I had a white wine. We stood in a corner and fondled each other. It was obvious that he was very well endowed so I suggested that we went somewhere else.
I took his hand and led him into the gent’s toilets.
We went into a cubicle and I sat down on the toilet and undid his jeans. I pulled out his huge black cock and licked the head. I slid it into my mouth and undid the button on his jeans and let them fall to the floor. I lifted his T shirt and ran my fingers over his six pack torso and down to his tightly curled pubic hair.
He removed his shirt and I could see that he worked out, his body was fabulously muscular. My pussy started to salivate at the thought of me pressing against it.
As I stood up I Iet my tongue glide over his body. I kissed his chin and unzipped my dress and hung it on the back of the door.
Fuck me I whispered and threw my arms around his neck. He grabbed my arse cheeks and lifted and turned me and pressed me against the tiled wall. Shit it was cold and my nipples were rock hard. I gently bit his thick black lips and occasionally slipping my tongue between them.
His intensely dark eyes were burrowing into my soul as he lined up the head of his cock with my dripping pussy.
He gripped my arse cheeks hard and thrust into me, all the air rushed from my lungs. I didn't realize how big he was. It was tearing my vagina to pieces, God it hurt but in a good way. He slid one of his fat fingers into my arsehole and I had an orgasm. I bit on his shoulder to stop me from screaming. This made him drive harder into my hole. He was now smashing my womb to bits.
He pushed the finger in as far as it would go and then I felt his scalding hot seed spraying right up into my body. He did several hard thrusts and pinned me hard against the wall, my breasts were flattened by his chest.
I was totally overwhelmed and I started crying. I kept saying thank you over and over as my tears dripped off my face and onto his chest.

When he had come down from his climax he kissed me and lifted me off his softening cock and placed me back on the toilet.
I started licking his cock and balls clean and I could feel some of his cum dripping out of my massively stretched pussy.


As he bent down to pull his jeans up he licked some of his cum off my lips and then put the finger he had fucked my arse with in my mouth. It tasted bitter but I suppose it was a new experience.
He put his T shirt back on and unlocked the door. Bye baby he said and left. I reached out and relocked the door.
I sat back on the toilet, my pussy was throbbing so I reached between my legs with my right hand and felt it. I put one then two fingers in, god it had been stretched. I tried three then four, I was ruined I said to myself.
I lifted my fingers to my mouth and tasted his cum. It was salty with a hint of spices. I put my hand back and pushed more cum into the palm of my hand, then licked my hand clean. It was the best cum I had ever tasted.
I stood up, my legs were still weak, and put on my dress.
I walked from the cubicle and went to wash my hands. I looked to my right and there were three guys pissing into the urinals. Two of the guys were old and their piss was colourless but the guy nearest to me had a golden yellow stream and his foreskin was rolled back to display a wonderfully pink head. It looked so yummy. He looked at me and I licked my lips and smiled.
I swiftly moved to the hand dryer with was between the sinks and urinals. The other two guys had finished pissing but stood holding their cocks and watching me.
I let my hand slowly go through his golden flow, it was hot and then I put my fingers into my mouth. It tasted bitter but not unpleasant.
One of the older guys said than is discussing young lady, zipped his flies and went out without washing his hands. I whispered to the young guy not to move and went to the remaining guy and turned him around to face me. I lifted my tight dress and crouched down and took his cut cock in my mouth. He groaned and a small amount of piss ran into my mouth which I gladly swallowed. His cock was small but hard so I sucked and licked him until he came. He was gasping for his breath and he was shaking like a leaf.
I made such I got all his cum and stood up. Thank you he gasped, you have made an old man very happy he said. I kissed him full on the lips and giggled.
He washed and dried his hands and went to the door. Excuse me I shouted, he turned and I pointed to his cock still sticking out of his trousers. Oops he said and we both laughed.

I turned to the younger guy who was still stood with his cock out at the urinals. Good boy I said even though he was older than me. I took hold of his cock and lee him into a cubicle when I sat on the toilet and took his growing cock into my mouth.
I pulled the top of my dress down so he could fondle my breasts which he did with great skill.
I let my lips and tongue travel the length of his wonderful cock and he was puling and twisting my nipples hard. It hurt but I like some pain.
He gave out a guttural groan and his thick and hot salty cum spewed down my throat.
After the last morsels of cum drained from his I removed it from my mouth and rolled the foreskin back over his glands, making sure I licked the last bits of cum of the end as it dripped out.
I stood and put my breasts back into my dress. I kissed him on the lips and licked them knowing that some of his cum would be left on his soft lips.

I left the cubicle and went back into the main bar, I had been missing for far too long and I needed a drink. As I ordered I felt a hand on my left ass cheek. I turned and saw it was the old guy I had blown in the toilets. I'll get that he said then whispered in my ear after such a wonderful blow job.

He asked me what a young lady was doing in a bar like this. I told him about my quest for the ultimate sexual experience. His eyebrows lifted in astonishment and said that was some goal. I told him about my life and how I was now staying with Jules and Jenson until I got some place of my own.
Then he dropped a bomb shell, come and meet my wife he said.
What, I had just given him a blow job and now he wanted me to meet his wife. It totally scrambled my mine.
Come on she doesn't bite unless you want her to he said and led me over to a table where a stocky woman was sat.
Mary, this is the young lady I was telling you about he said. I nearly fucking died, he had told her I had sucked him off, shit. You were right Sid she is very pretty she replied.
She stood up and kissed me. She had huge grandma type boobs that sagged slightly and her arse was large too. She was wearing a tweed suit, the jacket pushed her boobs together to from a big cleavage and her skirt went just below her knees like an old fashioned school mistress.
Sit down child she said and tell me a bit about yourself. I sat and she held my hand close to her crotch. Sid sat on the other side of me and placed his hand on my right thigh just above my knee.
I told her all about my goal and how I was homeless. She listened without once saying anything. I suddenly felt fingers creeping under the hem of my dress. It was Sid's hand, I never even felt him move up my thigh.
Mary took my head in her hands and kissed me so passionately I was fighting for my breath. Sid's hand touched my mons and I squealed softly. There child Mary said, Sid only wants to return the favour.
He is not going down and eating my pussy in public I said to her. Let's go back to our place then she said. OK I replied, I will just tell my friend were I am going.
I walked around the place until I found Jules and told him where I was going. WOW you've hit the jackpot there he said. S and M's . That will certainly take you to a new sexual level he said. Think of an easy to remember word and tell them. That is your safe word if it gets too much for you. He kissed me and said enjoy and I hope to see you tomorrow at some point. Thank you and you will I replied and went back to Sid and Mary.

Little did I know what I had gotten into.