The Very Stupid Boy Ch. 03

After I had driven home to my one bedroom apartment in North West England I unpacked, threw my dirty clothes in the washing basket then had a good long shower before pulling on a pair of jogging bottoms and a t-shirt.

In the shower when I was washing myself and my fingers grazed my hole, I shivered but went no further.

I sat on my sofa and wondered what was happening to me.

'Was I gay?' Of course not. I liked girls. I had a girlfriend!

I decided it must have been a one-off and as I doubt I would ever be in Birmingham alone again. It would remain a one-off and a secret.

Suddenly my phone rang.

'Hiya babe! Did you miss me?'

'Oh hi Amber. Seeing as I spoke to you every night I think missing you was not an option.'

'Want me to come over or will you come out with the guys tonight? We're going to the pub.'

I cried off, telling her I was too knackered from the drive back. We agreed she would stay over the following night and I would cook dinner.

I sat back, had another sip of wine before turning on the television and surfing the channels.

The next day I went out shopping and prepared a dinner of Coq au Van with green vegetables.

I set the table, placed a candle on it and opened a bottle of Merlot in time for her arrival

Amber is crazy, lovely but crazy. She is about five feet four, eight and a half stone with full breasts and a peachy arse. She is a typical blue eyed blond.

She is far more sexually experienced than me and initially I was surprised she wanted to be with me. She was a friend of a friend and soon hung around with our 'gang' that comprised of both sexes.

Apparently she thought I was nice as well as cute and she said she'd had enough of dating arseholes.

The dinner went well and we snuggled up oh the sofa with our wine and watched a romantic comedy before going to bed.

'Oh babe, I've really missed you. I hope you're not going to be too tired for me as we've got a lot of catching up to do!'

I started well. I know she loves it when I give her oral sex so I made sure she came three times before I let her return the complement. She didn't bring me off as she said I lose interest once I've cum.

She rode me to another orgasm then I took her doggy style lovingly watching her cute white bum moving over my rock hard cock.

I took her in the missionary position so I could feast on her perky but full C sized tits.

As I was pounding into her I could feel her hands cup my arse cheeks then she dug her long manicured nails into my fleshy orbs. I moaned!

'Fuck! Don't do that or I'll come!' I panted.

'What about this then!' she replied.

Without warning she slid the middle finger of her right hand deep inside my arse.

'Oh fuck!' I cried as I exploded inside her grasping cunt.

Her legs wrapped around my waist as I came and came triggering yet another orgasm for her.

I flopped on the bed, my chest heaving and my eyes closed.

When I'd recovered I looked to see her lying on her side, elbow on the bed and her head propped up by the palm of her hand with the biggest shit-faced grin I had ever seen on her.

'Trudy said I should do that!'

'What!' I gasped incredulously.

'Trudy. She used to do it to Brian all the time. She even bought a strap-on so she could fuck him in the arse!'

'What?' I said again.

'Yeah, she said plenty of guys love it. Hey, maybe I can borrow it now she's split up with Brian. What do you think?'

'Er.... maybe that's not a good idea.' I managed to croak.

'We'll see, night babe!'

I didn't argue so I turned off the light and fell asleep.

We had a nice day on Sunday just pottering about the apartment then she went home as we both had work the next morning, me at the bank and her at the beauticians,

The week dragged but each night my thoughts were all about Kim's cock and Amber with a strap-on. Did I really want to go there? I knew I wouldn't go with another guy but could I enjoy a fake cock in my arse?

On Wednesday Amber called.

'Babe, I'm sorry I meant to tell you on Saturday but we were having too much fun and it completely slipped my mind on Sunday and....'

'Amber! What is it?'

'Oh yeah. Listen I can't see you this weekend. It's Vicky's hen night in Blackpool and I'll be staying over at Tracey's house on Friday night as it's an early start on Saturday. We've booked a guest house for the whole twelve of us, three to a room but it should be fun so I won't be back until late Sunday afternoon.'

I told her that she would have a blast and I would probably go out with the boys on Friday night.

It was a good night as we trailed around a few of our favourite pubs, some wanted to go onto a club but I said I was heading back at midnight.

I was lying in bed on Saturday morning stroking my inevitable morning hard on wondering what I was going to do.

I thought about searching for massage parlours thinking I might just get a happy ending if I chose the right one when I suddenly thought about Kim's sister.

I got her card out of my work suit jacket pocket and noticed she was based in Manchester which was only about twenty or thirty minutes away by car, depending on traffic.

It was eleven o'clock by the time I built up my nerve to call her.

When she answered I told her that her brother had given me her card and said I should call her.

'Ah!, you cute boy. Kim told me about you. He say you would call. You want come and see me?'

I asked if she was working that day.

'No, I not work weekends.' My heart sank! 'So good time for you to come today as friend, not customer!'

'Really? Wow! That would be great.'

We agreed a time and she texted me her address which was in the city centre so I decided to go by train instead of driving.

I found her apartment complex, very new and very smart. I called her to say I was downstairs and she told me how to gain access.

Apartment five on the fifth flour. I knocked and waited. Less than twenty seconds later the door opened and a voice behind the door invited me in.

When she closed the door and I saw what she was wearing I nearly groaned out aloud, instead I just caught my breath.

She was beautiful. Long black hair hanging down straight to the small of her back, high cheek bones, large oval brown eyes, a cute nose with a full mouth and gloriously white teeth. I thought she was about my age, maybe a year younger.

It was really what she was wearing that had taken my breath away.

She stood at my height, five feet eight but that could have been because of the five inch high patent leather shiny black heels with ankle straps.

She was slim with her breasts pressed together by a latex half cup bra.

On her body she was wearing a shiny black latex corset that was tucked inside a long black latex skirt that went down to her ankles.

I thought that it was a funny thing to wear to massage me.

'You come!' she said as she led me into her lounge.

'Sit!' she said pointing at a black leather armchair while she sat in the middle of her three seat black leather sofa.

As she crossed her legs her latex skirt slid to one side revealing a dark gray thigh high stocking clad leg. My cock grew even harder in my shorts.

'So Kim fuck you, cutie boy?'

I was so embarrassed that my eyes looked down at my feet and I just mumbled something and nodded my head.

'He say you have nice tight arse. You good fuck. I like that.'

I looked at her and saw she had a huge grin on her face. Was she playing with me? I smiled back at her.

'So you come to see Ladyboy Ling! What do you think?'

I told her I thought she was stunning and that I was looking forward to receiving a massage from her.

She frowned for a second then shrieked with laughter.

'You no read my card?'

'Yes!' I said and fished the card out of my pocket.

'No! I retorted and instantly felt very stupid.

On the back of her card was her name and telephone number and on the front was her picture but at the bottom, obscured by my thumb was writing. I held the card at the side and read the word 'Dominatrix'.

'Bu..but Kim said......'

'Kim thinks I do massage. I did but this makes more money. He no know what dominatrix mean so think I still do massage.'

'Bu.. but I er....how much?' I realised I didn't have a lot of cash on me.

'No money. You come as friend of Kim.'

'But I've never...I have no idea...'

'Cutie boy, you just do what I tell you to do. OK?'

I wasn't sure I wanted to be dominated.

'I say OK. You understand?'

'Ye...yeah.'

'You understand?' she asked a lot more forcefully.

'Yes. Yes, I understand,' I replied anxiously.

'Good. Now take off all clothes and leave by your chair.'

When I was naked she told me to follow her and headed towards another door.

The door opened outwards and I noticed a dark room lit by small lamps in each corner of the room, the windows must have been blacked out.

There was a large black vinyl padded mattress on the floor and at the end of it was the second leather armchair.

She closed the door.

'Kneel!' she ordered.

As I went to bend down she walked past me and sat in the chair.

'Crawl to me!'

As I shuffled along the mattress she crossed her legs once again and once again her skirt split open giving me an even greater view of her shapely legs.

She just gazed down at me and when I followed her gaze I noticed my cock was rock hard.

She smiled then said, 'Kiss my shoe!'

With one leg over the other the shoe came to the height of my face.

I hesitantly placed a small kiss on the tip of the shoe.

'Kiss it like you mean it!'

I must have kissed it to her satisfaction as she ordered where to plant my other kisses.

'Kiss my heel!'

Her five inch heel was stiletto thin.

'Suck my heel. Just like Kim's cock, yes? Nice and slim.'

To this she gave a little laugh as I sucked the black shiny heel into my mouth. I thought it was lucky she didn't wear the shoes outside but then I wondered how many other 'slaves' had done the same thing.

She uncrossed and recrossed her legs again so I could do the same to her other shoe.

When she was satisfied to told me to sit back. I rested on my haunches.

She then stood up in front of me and unclipped her long black latex skirt, throwing it to one side.

I marveled as she stood wearing only her latex bra, shiny black latex corset, her hold up stockings and a black latex thong that bulged ominously at the front.

'Take off my panties!'

I gulped then gingerly reached up and took hold of the sides of her thong and slowly dragged it down over her cock and down her thighs then off.

Her cock swayed but it didn't look fully hard. Even in that state I guessed it was as long and as thick as my own seven inch cock.

I looked up at her and marveled.

'How can a beautiful, feminine, soft spoken woman have a man-sized cock?' I wondered.

She started to slowly stroke it as I watched it grow to maximum effect.

'You like, cutie boy?'

I just stared at it as her fist went up and down its length then over the cut head that was shaped like a bullet, a dark pink bullet. I was intrigued as my cock is uncut.

Then she walked behind me and I could feel her kneel as she wrapped her arms around me. I could feel her hard, hot cock press into my back as with one hand she took hold of my cock and with the other she stroked my left nipple.

'I am going to enjoy having you cutie boy!' she said as she squeezed both my cock and my teat. I groaned.

'Turn around!'

I shuffled so I was facing her. Her right hand went to the back of my head as she pulled me in for a passionate kiss. As her tongue found mine her left hand sought out my cock.

I moaned into her mouth as she gently stroked me.

Her right hand swept down my neck, along my cheek and down between us. She broke the kiss and looked at me, staring into my eyes.

Her left hand easily pulled back my foreskin as pre-cum dripped down over her fingers.

I moaned as I felt the head of her cock rub against my own.

She used the head of her cock to rub around and around the head of mine as she stroked me harder. The feeling was incredible as she kept up the pressure with the head of her tool.

I looked into her eyes then down to her latex clad breasts.

'Oh fuck!' I cried as she teased me to within a second of cumming.

She whispered in my ear, 'If you cum on my cock cutie boy you will have to lick it all up!' As she said that she gently bit my ear.

'Oh shit. Of fuck. No!' I cried as I exploded all over her shaven crotch.

She leaned back with her hands holding her ankles. I looked at her cock and small hard balls covered in my cum.

'Clean!'

I bent down to where most of my secretion had landed and almost lovingly licked and sucked my cum from her throbbing cock. She moaned as I sucked her balls clean which prompted me to lick her shaved pubic area.

We made eye contact as she smiled then reached behind to remover her shiny latex bra.

Her perfect thirty four B cup breasts stood up proud on her chest with her prominent thick, suckable nipples standing to attention.

She nodded down to her cock.

I knew what to do as I opened my mouth and my lips descended onto it.

I sucked it gently at first before practically making love to it with my mouth.

Still leaning back she placed her hands either side of my head to hold it still then proceeded to face fuck me hard, drool leaking out of my lips and causing me to gag on several occasions.

'You have nice mouth cutie boy! Now I think I fuck you.'

She had me lie down on my back as she picked up a tube of lube which she worked into my arse with her middle finger.

When she added her forefinger as well I was moaning constantly. By the time she added a third I was practically hyperventilating,

Once she thought I was loose enough I saw her take a condom, rip its wrapper off and stroke it down over her rock hard cock. She added more lube over her rubber coated tool and told me to grab my thighs and hold them up as high as I could.

I held my breath and bit my lip as the head of her cock touched my hole. I was glad it didn't have a mushroom end so the first inch slipped in quite easily.

She then eased more of her meat into my arse as I groaned, not in pain but definitely in pleasure. She looked so beautiful as she concentrated on fully entering me without hurting me.

When she bottomed out she began to fuck me slowly, by now my feet were on the floor with my legs wide open.

Her strokes were getting stronger, rubbing over my prostate and increasing the sound of my groans.

I could see my now hard again cock bouncing as she plowed me so I took hold of it with my right fist and pumped it as she pumped me, the feeling was incredible.

After a few minutes of her fucking me and me looking at her, her breasts heaving and her beautiful face which seemed to be engrossed in pure pleasure I could feel my balls starting to churn.

'Oh God Ling, I'm going to cum!' I cried.

'Good. I fuck the cum out of you!' she replied between grunts as she upped the pace.

'Oh shit!' I erupted over my chest and fingers as they flew up and down my rod. It just kept cumming as she kept fucking my arse.

Eventually my hand dropped to my side, I felt drained but Ling didn't stop.

'I think time Ling cum!' she stated as she pulled out of me and ripped the condom off before throwing it to the floor.

Still stroking her cock she made her way over my body until she was kneeling over my face.

'Suck my balls!'

I licked and sucked her cute little balls as I absentmindedly took hold of my cock again. It felt amazing as it tingled in my hand.

'Open mouth and stick out tongue!

She was now masturbating furiously inches from my face as I started to wank myself faster.

'Here comes!'

The first blast hit my cheek, the second spurt went into my mouth and the third landed on my tongue. Suddenly she pushed her spasming cock into my mouth as I groaned around it when I had a third but weaker orgasm, my cum dribbling out of me as I sucked the cum out of her and swallowed it.

We both lay side by side for a few minutes to get our breath back.

Eventually Ling said we should both shower and led me into an en-suite where she gently soaped me. I took the hint and did the same to her, sponging her breasts.

She handed me a towel and told me to get dressed. I dried myself, made my way to her lounge and pulled on my shorts and polo shirt.

I was sitting in the armchair when Ling came back in. She still looked gorgeous wearing a large fluffy white dressing gown, her long jet black hair still wet as she padded over to the sofa in her bare feet.

'Come sit!' she told me.

We sat with me with my arm around her as she cuddled up to me.

'You want to stay here tonight?' she asked as she looked at me with those big brown eyes.

I really didn't know what to say. Part of me never wanted to leave but then I thought of Amber and suddenly I was flooded with guilt.

'I er.. I can't.' I said weakly.

'You have girlfriend?' she asked. I nodded quietly.

'I understand.'

She suddenly looked sullen.

'Ling will never be girlfriend.' she said sadly, looking down at her crotch.

I told her she was a beautiful woman and that one day a lucky guy would sweep her off her feet.

This cheered her up.

'Maybe I can be your ladyboyfriend?' she said with a giggle.

I gently kissed her on the lips which turned into a full on snog.

'Yes, you can be my ladyboyfriend.' to which she screamed and thrust her arms around me, hugging me tight.

I left soon after but not before Ling reminded me that she had my number and made me promise to keep in touch on WhatsApp.

I wandered around Manchester City Centre before finding a bar on Deansgate that did tapas. After a couple of glasses of chilled white wine and a few small tapas I decided to go home.

It was early evening when I eventually got home so I ordered a pizza, opened a bottle of wine and tried without luck to watch a movie on Netflix.

That night in bed my mind was in a whirl and it took me a while to get to sleep.

Sunday morning was a quiet affair with me pottering around the apartment.

At five o'clock my phone rang and a very tired and hung over Amber groaned out a 'hi babe!'

She began to tell me about her weekend and how much they had all enjoyed it. How she didn't pull but could have and telling me she missed me. I felt so much love for her just then.

'Oh and babe! I bought us something.'

I hardly dare ask.

'The was an Ann Summers shop near our bed and breakfast so I popped in and bought us a really lifelike strap on. We're going to have so much fun!'

I groaned, she laughed then we said our goodbyes and agreed to meet midweek.

On Tuesday as I was on my break at work my phone pinged. I saw it was a message from Ling so I took myself to the toilet to open it.

All it said was 'Miss me?'

I quickly answered back.

'Yes!'