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My First Time - I think!

That special moment when a man finally made me a woman!
I left my very expensive and very well known Ladies College in June 2001 due to begin Uni in Southampton in September and was totally in the dark about guys. It now seems crazy to admit that at the age of eighteen the extent of my knowledge consisted of gossipy tales (probably made up) of sexual encounters passed around the girls in my dorm, no doubt embellished and dramatised along the way. Then I met Jonny, a leather jacket and everything black kind of guy, a little on the dangerous side and very moody and my very first sexual encounter quickly followed.

Jonny was older than me and very cocksure which was strange because, as I was about to find out, his cock was much less than I had expected from such a macho type and when it came down to it, he didn’t really know how to use it! What followed was disappointing to say the least and in the dreary confines of the back of his dad’s car, he jerked off almost the instant he found where to put it leaving me with my skirt in a mess and the feeling that this surely couldn’t have been my first time!

I decided to discount it. Like most girls I had dreamed of giving my ‘little cherry’ to a sweet, loving guy with flowers, gifts and champagne to subtle music with sexy lighting on a massive luxury bed. Cue Uncle Theo!

Uncle Theo wasn’t really my uncle at all but a lifelong friend of my Dad; he had been there all my life and gave me lovely presents at every birthday and Christmas and any other significant occasion. My Dad and Theo had business interests together and both had been very successful, giving me a very privileged upbringing for which I will be eternally grateful. I knew he had been looking at me in a very different way for the last couple of years, not as a girl but as a young woman and oddly I began to see him more as a mature but handsome man rather than ‘uncle’.

The disappointment with Jonny left me reeling, I had really fancied him, still did in fact, his macho dark features just what I had been looking for so I continued to go out with him but no way was I going to bed with him again. We went clubbing often, usually ending up in some dark alleyway, his hand fumbling around up my skirt and mine down his trousers giving him a handjob which seemed to satisfy him. How long could I go without getting some of the real action instead of his hot cream oozing between my fingers whilst he grunted in my ear?

I was certain Theo was the answer; I had stopped calling him ‘uncle’ when I was sixteen at his insistence and now I was going to go for him. Whenever I went up to London he would insist on taking me to lunch, having time-out from his busy and very plush office in the City and whilst it had all been very innocent, this time for me at least, was much, much different.

‘Hi Little Princess,’ Theo had chirped when I arrived, he had always called me that and I had always liked it, but not today, I wanted to be something other than his ‘little girl sort of niece’.

He had ordered a taxi and off we went to a very smart hotel just off Park Lane, all glass and steel, shimmering in the midday sun as we glided up to the main entrance. A concierge in navy blue and gold expertly timed our arrival and swished open the door for me, standing politely as I emerged trying not to show him my knickers as I slid from the back seat.

The maitre’d showed us to a small but nicely placed table by a massive window and held my chair as I sat down, noticing other diners swivelling their heads around to observe our passage through the restaurant. I had been to restaurants with him on many occasions but this time was very different and I could see that Theo was uncomfortable with the looks we were attracting.

‘You look different today, Nikki,’ he said politely.

I certainly did. I had specifically chosen my deep blue satin dress for its figure hugging design, clinging to every part of my like a second skin, a perfect fit even over my prominent bottom. My bare tanned legs tapered from my fairly short hem to a pair of gold strappy Jimmy Choo’s with four inch heels, ironically another gift from ‘uncle’. Underneath I had carefully chosen midnight blue lace and satin bra and panties, not a thong but a high-leg, a bit of a compromise between a touch of VPL and something for his eye if I got my way and he finally unwrapped me. My dress was lined which minimised the effect my panties had across my bottom and as a bit of an extra ‘swished’ sexily when I crossed my legs.

‘Do you like it?’ I responded.

‘Of course, you look really stunning little Princess.’

‘Please don’t call me that!’ I snapped without thinking. His face displayed a hurt that suddenly pierced my heart. ‘Sorry Theo,’ I added quickly. ‘I didn’t mean to be rude but I’m not a little girl anymore, and I don’t call you ‘uncle’ now do I?’

The hurt quickly disappeared. ‘I’m sorry,’ he said. ‘I didn’t intend to be patronizing and yes, you are definitely no longer a little girl. You are a very pretty young woman, Nikki, I can obviously see that.’

‘Am I?’ I said fishing openly.

‘Of course,’ he said predictably. ‘You are without doubt the prettiest woman I have had the pleasure of taking to lunch in many, many years.’ He laughed and I joined in.

‘Why have you never married?’ I quizzed, shifting up a gear. ‘You are a very attractive and very successful man and yet hardly any women.’

‘Am I?’ now it was him doing the fishing.

I looked into his deep azure eyes and assured face, slightly tanned with jet black hair, neatly trimmed at the sides but slightly long at the back. He is six foot minimum, not lean or skinny but solid with a healthy, slightly muscular body. ‘Oh God, yes,’ I breathed and immediately blushed, did I really intend saying that. I had shifted up yet another gear. I cleared my throat and changed into reverse. ‘So why no wife?’

I could tell he was assimilating my previous statement whilst answering the last. ‘The woman I loved married another guy,’ he said suddenly slightly downbeat.

‘Oh God, that’s really sad,’ I said almost in a cry.

‘No it’s not,’ he answered quickly. ‘She is very happy and with the guy she really loves.’

I wanted to ask more but felt I had already delved into some tricky territory. I had to get back on track. ‘Any particular woman at the moment?’ I ventured.

‘No,’ he said simply, ploughing a fork through the Caesar Salad we had both ordered. ‘Why?’

Oh. I tuned the salad over with my fork like mixing something, not eating it as that was not what I was here for. What could I say, ‘Hey Theo, I think I’m still a virgin can you take me to a room and fuck the heck out of me?’

‘I’m still a virgin,’ I blurted.

Theo nearly choked on his lettuce. ‘You can’t be,’ he said in a much too louder voice. Then realising that ears were nearby he leaned over his plate towards me. ‘Nikki, you’re eighteen. What are you fucking around at?’

‘Well, for one thing, I’m obviously NOT fucking around, or I wouldn’t be a fucking virgin.’ Ears twisted in our direction like satellite dishes.

‘Why are you telling me?’

I somehow managed to answer him without words and I watched his face as the penny dropped.

‘You are joking, right?’ he was stunned and so was I. I thought he would jump at the chance to jump me! I motioned my hands over my dress and gave him a sexy pout; well at least I thought it was. ‘Jeeez,’ he whistled. ‘You’re not joking are you?’ Yep, the pout must have been sexy. ‘What’s wrong with a boy your own age?’

‘You said it, ‘boy’. I need a man. Theo, I need you!’ There, I’ve said it; no going back now. I didn’t want to.

‘What’s the plan?’ he began. ‘You want me to get a room and take you to bed, give you a fucking like some hotel hooker?’ His voice indicated both annoyance and some disapproval of me. Suddenly I was mortified.

‘Yes.... No!’ I shrieked, other diners were logging onto our conversation. ‘I’m not a hotel hooker,’ I squeaked, now it was my turn to wear the hurt face. I downed my fork and prepared to leave, retrieving my handbag from the floor by the chair.

‘No you don’t young lady,’ he said forcefully reaching across the table and grabbing my wrist. ‘We need to talk.’ We dumped the meal and headed for the lounge much to the relief, or possibly disappointment of the other guests.

Theo ordered drinks and we sat in a quiet corner. ‘What’s this all about Nikki?’ he ordered.

Time to come clean. ‘I fancy you,’ I squeaked stupidly. No that wasn’t it. Try again. ‘I don’t love you or anything like that.’ No, no, no, that’s not right, try again. ‘I love you, but not like that...’ Hopeless!

‘Nikki,’ he said in a very commanding voice snapping me out of my witless rantings. ‘What do you want?’

I looked at him like a vamp yet felt like a silly girl. ‘I want you to take my virginity. I want a real man who I respect and admire; it just has to be you Theo,’ I finally said in a very confidant and assured voice.

‘What about your parents?’

‘I’m not about to discuss losing my virginity with them am I. They don’t need to know.’

‘There can be no future for us,’ he said laying it on the line. ‘Pretty as you are Nikki, you are not the woman of my dreams for marriage and beyond.’

‘Oh, god no,’ I squealed. ‘No way, you’re way too old for me.’ I really didn’t mean to say that, but it was true. Luckily he didn’t pick up on it.

‘Good. Now we agree on that I’ll get us a room. Okay?’

‘Oh god, yes please,’ I oozed, my words seemingly melting on my lips.

My stomach churned wildly and my pussy tingled in a way I had never felt before as the elevator glided upwards. The bell clanked and the doors slid open almost silently, Theo leading me by the hand along the thickly carpeted corridor. Anyone passing would think, old man with hotel hooker, but I didn’t care, in fact that added to the excitement. He swiped the lock and swept me inside the sumptuous room. My panties felt damp as the door swung shut behind us.

This was no time for small talk but a bottle of Champagne sat on ice in a tripod bucket by the bed. He was very thoughtful; I had the big luxury bed, the bubbly, a sweet mature guy, but no music. Fuck the music, I thought as the cork banged out of the neck of the bottle, he handed me a glass and I downed it in one, discarding it on the dresser then reaching behind me to unclasp my dress I pulled the zip and down it went. The midnight-blue satin swooshed down my body into a heap around my Jimmy Choo’s and Theo’s eyes popped forward as he homed in on my matching lingerie.

Had I overdone the perfume? The scent from my ‘Touch of Pink’ seemed to fill the room but if Theo minded he certainly didn’t show it, removing his suit jacket to the back of a chair then going for his quite jazzy silk tie. I stepped forward right up to him and took over the pleasure of slipping the knot for him, my fingers trembling as I fumbled with the buttons on his crisp white shirt, he pulled it from his waistband and slipped it off his shoulders.

I had seen him topless before at countless swimming lessons and parties as I was growing up but this was different, so very different! Never before had I noticed his fairly trim torso, almost a six-pack sheathed in a lightly tanned skin and looking much younger than his years. I felt my nipples harden inside my bra and my pussy ached for some action, this was IT!

Theo ran his hands over me, lightly feeling my skin which tingled sensually beneath his palms, I shook my almost waist length hair to straighten it down my back and stuck out by breasts, wanting him to admire me as a woman and not a girl. He leaned forward and kissed me gently, fully on the lips and I melted like butter on a griddle, sizzling and full of fizz, my hand went straight to the front of his trousers, I really needed to know if I was turning him on.

OMG! He was huge, and I mean really huge! How could I not have known he was so big, all those years on beaches and swimming pools and I never knew, my fingers seemed to go on and on tracing his length inside his neatly pressed trousers; I unzipped him and delved inside. It was so hard and hot yet felt soft and warm as I attempted to wrap my hand around it to pull him out. His cock popped from his opening and splayed out fully in my palm and I just had to get a look at it.

I sucked in breath as if I was going under water as I took in its beauty, slightly dark pink with a helmet of almost purple standing elegantly from its cropped shaft, no foreskin just pure cock! The only reference point I had was that of Jonny’s feeble offering less than half the size with nothing attractive about it.

‘Would you like me to suck you?’ I said in a voice I just didn’t recognise, looking up into his gorgeous eyes. He nodded and I sank to my knees not caring if I scuffed my precious JC’s keeping them on to enhance the curves of my legs. It was only then as I confronted his erection bobbing gently in front of my face that it occurred to me, I had never sucked off a guy before! I had seen the porno films in the girls’ dorm and we had all giggled and played with ourselves over them but would I do him justice, or would I look a prize idiot?

I needn’t have worried, looking up I could see he was enjoying it as I popped the purple head into my mouth, lips enclosing it just behind the flange, cheeks sucking in to vacuum pack his man-meat. I bobbed back and forth slowly at first then picked up a slightly faster rhythm as his hand began to stroke the back of my head, this was just Heaven. He tasted so good! I hadn’t known what to expect but it was just awesome, the feel of him in my mouth just made me want more, the slightly sweet yet salty taste tantalising every part of me.

I couldn’t believe how much cock I could get inside my throat yet his generous length had all but disappeared between my lips, my nose getting tickled against his surrounding pubic hair and now I was sucking him like a whore. I felt like a whore and at that moment wanted to be a hotel hooker and be treated like one! Reaching behind me with both hands I unclasped my bra without breaking stride on his cock and looped it from my shoulders discarding it to one side, Theo immediately reached down and caressed them with his strong hands, fingers tweaking my rock hard nipples.

My panties were soaking when I slipped a hand between my legs to rub my pussy and nearly came at the lightest touch of my fingers, I wondered how I would do when Theo finally slid into me. I was about to find out, his hands left my breasts and egged me up by my shoulders, raising my head to kiss him, hands working my panties over my bottom and down my legs.

‘Keep your shoes on,’ he husked as I kicked off the panties, he had already removed his and his trousers were going the same way as my pants, his shorts and socks seemed to have vanished in a blur and he was laying me on my back, spreading my legs as I went. His head disappeared from my view and then a rush of ecstasy as his tongue flicked against my wet pussy sending me dizzy in a way I had never before experienced. He was on the hard nub of my clit and my vision blurred, the ceiling dancing back and forth then I felt his fingers probing me and I squealed before realising it, trying to keep to some kind of dignified moan but it was no use, fuck anyone listening in the next room!

Theo was coming up me, licking my tummy then my breasts as he surfaced, the hard heat of his cock trailing behind him, tickling my thigh as he headed for my womanhood, then he took me! This was what it had all been about, losing my virginity in a sensual encounter and in a moment his rock hard cock had parted my pussy lips; that purple angry looking head pushing into me. I was shrieking uncontrollably, hands clenching Theo’s back as his cock sank further into me, my virginity, if it had been there, gone at last!

Now it was Theo making sounds as his lower half pounded against me, using his erection to full effect inside me then I bit his ear as I jerked out of control, my juices streaming into the void between my channel and his cock.

‘My god Nikki, you’re so hot and tight, just like your mother,’ he whispered.

His words buzzed in my head then I suddenly froze, did he say ‘just like your mother?’ I was writhing beneath him struggling to get from under but he was too strong and held my arms pinned to the mattress, he withdrew from me gently. His face seemed shocked at my sudden reaction. ‘You said just like my mother,’ I shrieked, struggling again, this time he released me and I got onto my side. ‘You and MUM!’ I squealed.

The realisation suddenly hit him. ‘No, Nikki. You don’t understand,’ he said softly trying to placate me but I wasn’t having any, I tried to get off the bed but he held me, firmly but not harshly. ‘Your mother would never cheat on your father, NEVER!’ he said raising his voice.


‘No buts, Nikki,’ he reacted. ‘I knew your mum before she met your father, in Brazil when me and your father went out in the early days to get some contacts for our new business. He had to come back here to look after things and I stayed and met your mother and we got close,’ he began. I noticed his eyes becoming misty with the recollection. ‘I intended marrying her and bringing her back to England then your father returned and I introduced him to her and she fell for him in an instant. He brought her back and married her and the rest as they say...’

‘So how did you...’

‘We slept together before she even knew your father, in fact she was a virgin, just like you, eager and in love, or so she thought and we made plans but when she met him it was all over.’

Suddenly a veil lifted. ‘Oh god,’ I squeaked. ‘She’s the one you talked about, the woman of your dreams. Oh Theo that’s really sad.’ I suddenly felt like crying but he reached out and held me.

‘Like I said earlier,’ he husked. ‘Your mum is very happy; she is in love and not with me. Yes I did love her, in fact I still do but in a very different way. She would never, and I repeat, never go with another man, your father is her one and only true love and I am very happy for them both.’

‘You took mum’s virginity?’

He nodded, embarrassed and suddenly unhappy. He let go of my arms and began to get off the bed.

‘No,’ I said quickly, reaching out for his hand. ‘I don’t want you to go,’ I said softly knowing what I wanted. ‘You haven’t finished yet.’ I smiled pointing to his wilting erection.

‘I don’t think its right .....’

I stopped him with my finger across his lips. ‘Fuck me Theo,’ I husked reaching for his cock, massaging him tenderly. He grew quickly between my fingers and I lay back waiting for him to take me again, hovering above me he said quietly ‘are you sure?’ I nodded and he entered me once more and I squealed as he worked me towards another climax. It was strange having a man take me just as he had my mother all those years before but somehow it heightened my experience and I flooded him quickly, he reacted with several jerks between my legs, pumping his cream into me with a passion I knew was for her rather than me!

This story is protected by International Copyright Law, by the author, all rights reserved. If found posted anywhere other than with this note attached, it has been posted without my permission.

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