Story Code: M/f, First time, Pay-for-play

I had known the Jackson family for some years and enjoyed their company on many social and party occasions. They were a lovely family...four great children, one boy and three girls, and I had watched them change and mature with amusement and joy. The youngest, Elizabeth was the one who caught my eye. She is about 5ft 4" high, and slim, some might say thin. I had met her first when she was a leggy 12 year old and now she was a leggy 17 and becoming a young woman. Blond shoulder length hair, blue eyes, pretty lips, pink clear skin, a pert bottom and small 32a breasts completed this vision of a lovely young girl, becoming a woman... She was brought up strictly, but when our families were together, she seemed always to have the time to come and talk to me about her life and the things happening to her. I always tried to be encouraging, and keep her spirits high, and in return I sometimes thought she was flirting slightly with me....but I felt it meant nothing...what could she see in me..? Our relationship was about to change.

Her parents asked if I could help them to teach her to drive, as they had a lot on their hands...I readily agreed, and honestly had no other motive than to help a nice family out...however, that was to alter. We had seven or eight lessons, with lots of chats, some quite confidential as she talked about her ambitions, and her friends. I asked if she had a boyfriend and she went a little thoughtful. She told me she hadn't, and slowly, carefully explained that she didn't want to be expected to have sex, as most girls and boys seemed to be doing. I asked her why not. She replied.." I want to save my virginity for someone who cares, is experienced and will make it memorable for me." I commended her on her good sense, and we finished the lesson. When she moved to get out of the car, she turned and, putting her hand on mine, said "That was between you and me, OK?" I smiled, "Of course.....same time tomorrow..?"

The next evening, I picked her up and she drove beautifully around our usual route, but she seemed quiet, almost withdrawn. I asked her why. She explained she had no money, but wanted to buy herself a car. Her parents had offered to help, but she wanted to earn it herself. I asked her how much she needed. 'About £1000' she replied. 'That's a lot of money' I said...and she answered and said that she had no idea how she would raise it...Before I knew what I was saying, I responded that I did. She turned and looked at me, 'How?' I was now regretting my impetuosity...I began to colour up, and stuttered..'Oh, forget I said that, just a silly thoughtless response'. She caught my arm..'No, tell me..I want to know, I'm quite desperate..., please..' . 'OK, but you must not mention this to anyone, agreed?'...She nodded. 'You are a virgin, right?' She nodded again. 'I have never taken a virginity in my life, and I would love to do so'...she Reddened and I stuttered on. "If you let me take you to bed, and make love to you, I will buy you a car"... there, I had said it. She looked at me "Really?" I nodded my head. I expected her to get out of the car and never talk to me again. But no, she was considering it. "Can I give it some thought?" she asked. "You mean, you might?" I asked...she smiled..."Let me think....I'll phone you" she smiled again, pecked me on the cheek, got out of the car and without a backward look she went into her home.

It was almost 24 hours later, when my mobile phone rang. Hesitantly, she asked me how I was, was I busy?.. just small talk really. Then she began to talk quickly but nervously..."Yes, I want to take you up on your offer"...I could hardly believe my ears...I smiled and said, "You will be fine young lady, don't worry about a thing.. you will love it and be £1000 richer at the end..." She thanked me for being kind (!) and we closed off the call. The deal was done....

Two days later as arranged, I was in the foyer of our city's best hotel. I had decided that only the best hotel room would be good enough to deflower such a lovely young lady. I had already been up to the room and unpacked a few things and was drinking a quiet coffee, when Elizabeth arrived. I stood, shook hands with her, and we sat down, and I smiled at her..."Feeling OK?" I asked softly... she dropped her eyes..."A bit frightened, to be honest...this is all so new to me..." she whispered. I took her hand, her instinct was to draw away, but she relaxed. "You will be fine, don't worry about a thing...you are in good hands"..."I know" she spoke so quietly "there is no one else I would trust to do this with.. one thing I ask..." and she gazed at me with those lovely innocent eyes "Please be gentle with me..." I smiled... "of course, OK, I'm going to leave you here, I'll go up to room 303, and wait for you there, give me five minutes.. no make it three!' She smiled..."You are so eager...." "I am indeed, young lady" ...and I left her.

Three minutes later, almost to the second, there came a quiet knock on the door. By now I had stripped to my boxers, and donned a hotel bathrobe. When I opened the door I was greeted by the sight of a very nervous looking young lady, who was obviously 'battling her inner demons'...I held out my hand and she placed hers in mine and I drew her into the room. She stood awkwardly, evading my eyes. I moved behind her and helped her off with her coat, placing it carefully over an armchair. "You like the room?" I asked. She nodded "Beautiful".. and it was.. the hotel's top suite.. nothing was too good for this little lady. "Shall we get the business over first?" I asked. I pointed to a plastic bag on the bedside table. "That contains £1000, which is yours at the end of today's date. Happy?". She nodded. "I think so...but you must know I'm nervous. You do promise not to hurt me don't you?" I smiled..."I cannot promise....there is always a little pain, the first time, but I will be gentle and take my time.. you are in good hands".... and I drew her into my arms and hugged her, stroking her back..... she seemed to lean into me and even raised her arms to place her hands on my hips. I hoped she could not feel my growing erection. I backed away slightly. I lifted her chin and looked directly into her eyes.. "Trust me?" She smiled and nodded. "OK, I am going to caress and stroke you, touch you in places you have not been touched by anyone else before...just relax and try and enjoy it..." I smiled and took her back in my arms..I slid my hands over her shoulders, arms, and back up again cupping her face in my hands I lowered my lips to hers and gently kissed her, pressing into her, and she responded.. but only slightly. I lowered my hands to her waist and held her, pulling her against me, rubbing my erection against her. My hands moved to her bottom.. and pulled her into me, sliding my fingers up and down the valley between her buttocks, alternating with a firm grip on the globes of her firm bottom....lovely!

I turned her round so that she was facing a full length mirror...with my hands on her waist, I waited until her eyes met mine in the reflection and then began to move my hands over her body. I moved first of all to her tummy and stroked her in increasing circles. Her hands were to 'at' her sides, and she made no attempt to protect herself, as I began to move more intimately around her body. I moved both hands up to her breasts and gently massaged the small firm mounds. I slid one hand slowly down her body to cup her mons and massaged the her mound, pressing pulling her against me. She gave her first moan. I took one of her hands and guided it around her back and to my cock.. at first she pulled away, but I persisted and she held me through the fabric of my dressing gown, and gently rubbed me... "I think it's time we got rid of some of these clothes, don't you?" and smiled at her. She nodded, and I backed away from her and climbed onto the bed. I lay with my head on the pillows, and smiled at her again.. "Would you undress for me, please, Elizabeth?" She nodded, and dropped her gaze, and slowly lifted her hands to the buttons of her blouse. Starting at the top she undid them all and slid the blouse from her shoulders revealing her white cotton bra. Her hands went to the belt of her jeans and she began to unbuckle... undid the zip and slid them off her hips and down her legs. She stepped out of them slipping off her shoes at the same time. She stood with her hands at her sides and looked pleadingly at me. "Carry on, Elizabeth, I want to see all of your body.." She sighed with embarrassment and pent up emotion, reached behind herself, undid her bra strap and slid the flimsy garment off her shoulders, trying to cover her pert breasts with her hands. I motioned with my hand, and she dropped her hands showing me her lovely young bosom...perfect nipples, breasts the size of grapefruit, begging to be squeezed. I again motioned, and her hands went to the elastic of her white cotton panties, and slid them down her thighs, down her legs and onto the floor. She made no attempt to cover herself this time, and I was able to enjoy the sight of a pubic triangle covered with untrimmed teenage blond hair....delectable...!

"You are lovely, Elizabeth, come here and let me touch you." She moved to stand next to the bed and I opened my bathrobe so she could see the effect her naked body was having on me. I took her right hand in my left, and reached out to her with my right hand and began to stroke her arm and shoulder, I brushed her breast as I allowed my hand to move to her tummy, and out to her hip. I drew her nearer and slid my hand across her to lightly cup her pubes. She started, and pulled away...I drew her back.."Don't struggle, darling, it's going to happen, so just relax"....I moved my hand, let go hers, and allowed both hands to caress her breasts, gently at first, and then firmer, grasping her, and tugging on her small pert nipples. She winced. But didn't try to pull away. I slid my hand down her chest, over her flat tummy, to her mound, inverted my hand so that its or my palm faced upwards and 'I' slid my middle finger into her slit.. very, very slowly, backwards and forwards. "It would help me a lot, Elizabeth, if you would move your feet about 18" apart..." she did so, slowly, allowing me easier access to her vagina. I eased my finger inside her slit moving to and fro, little at a time, until it was inside her to the first knuckle.. she was starting to moisten on reaction to my touch and I could feel her body responding to the pleasure I was giving her. "Turn round, darling" I asked her quietly, withdrawing my hands.. she did so. Her perfect bottom was before me. 'Would you be kind enough to lean slightly forward?' I asked her. 'Now, can you touch your toes?' This had the double joy of tightening up her already taut bottom, and forcing her to place her legs apart, opening up her anus and her vagina for my inspection....I was in heaven. Perfect. And untouched. I gently probed her bottom and slid my finger into her anus... she kept amazingly still, and even pressed slightly backwards onto my finger...I withdrew... that would be later, or another time....!

"Clime onto the bed, sweetie"...and as she climbed aboard, I slipped off my robe completely and lay back, as she knelt beside me. I stroked her body unhindered by her hands which hung to her side...she seemed to have lost all shyness and allowed me free access to anything I wanted to touch, her breasts, arms, back, thighs, calves, feet...all freely and easily available. I did not even attempt to ease her knees apart to touch her intimately...plenty of time for that! "Have you ever seen a man naked?" I asked, already knowing the answer. She shook her head. "Would you pull my boxers down for me please, Elizabeth?" She nodded and leaned forward, slipping her fingers under the elastic, and slid them down. My cock was half erect, and she fixed her eyes on it.." Would you like to touch me?" She nodded her head shyly. "Go ahead"..and I took her hand and guided it to my cock...she instinctively knew what to do and began to gently slide her hand up and down, sliding my foreskin back as she did so, and feeling me harden in her hand..."You like the feeling of that?" She nodded her head "It's so hot and hard, and yet soft and silky" she commented... so appreciative.

I kissed her. Gently. Then harder, sliding my tongue into her opening mouth. I put my hands on the side of her head and held her and kissed her hard. She kissed me back. I could not believe it. Something is wakening here. "Lie back on the bed, darling" I said, and she immediately lay down hands at her sides. I eased her legs apart, bent her knees and knelt between them then I began to kiss her inner thighs, tummy and groin...Then I eased her legs over my shoulders. "Open yourself for me". She reached down with both hands, knowing instinctively what I meant, she slipped her fingers either side of her labia, pulling her lips apart, showing me her sweet inner pinkness. I lowered my head and began to lap at her...slowly searching until I found her nub of sensitivity...I felt her body responding...she moved her hands to my head and began to press pull me to her forcing me into the position that gave her most pleasure. She was moaning, sighing, and beginning to lift her body to me, opening herself and lifting her legs resting them on my shoulders.....I felt her first orgasm rack her body as she gasped and whimpered...pushing herself hard into my non-yielding mouth....then she sank back, winded with the effort. "I never knew....that was, was, so good...." she caught her breath..."I never knew.." she said again, smiling... "I know, Elizabeth, I know...and there is more to come...but right now, I think it's time...." She frowned..."What do you want me to do?"

"Lie on your back and lift your bottom for me"....I placed a pillow under her hips and lifted her knees and spread them wide enough for me to get easy access to her vagina. I reached for a tube of lube I had left on the side, and, putting some on the tops of my fingers gently probed her labia, and vagina, sliding my fingers in and out going deeper gently until I encountered her hymen. I gently pushed and she winced and sucked her lips...I drew back and stroked her clit for a moment or two. She would never be more ready than she was now. I knelt between her legs with my cock lined with her opening..I leant forward, nestling the head in her opening. Pushing her legs up and open I probed her vagina with my penis until I could feel the resistance of her virginity. I leaned further over her, and told her "Breathe normally, relax and look into my eyes" . She looked at me, and I began to move inside her gently stretching her, then, when I could contain myself no longer, thrust firmly into her breaking through her membrane... she gasped, her vaginal muscles tightened.. "Just relax, sweetheart, it'll be OK now..." I steadied myself, and held my position... fully inside her, allowing her to adjust to my invasion of her body. "All right, now?" I asked as I sensed her relax...she nodded, with a weak smile...and I began the rhythmic movement of sex... to and fro, in and out.. gently at first and then gradually increasing the my pace as I felt her response. her eyes were closed, and her hands were on my shoulders, her legs drawn up and open, and her pelvis meeting my movement with hers, maintaining a steady and increasing thrusting....I was soon to cum, I felt it...I forgot all thought of her, revelling in the tightness of her vaginal wall, and feeling her clenching my cock and beginning the time-honoured technique of milking... "Open your eyes, Elizabeth and look into mine...I want you to see into me as I cum inside you..." She did so...fixed her eyes on mine as I jerked violently into her; one, two, three, four ropes of potent spend shot into her unprotected body....

I collapsed on to her, my head next to hers, gasping air into my lungs...but I managed to hear her say...."Thank you, that was wonderful"....I smiled at her, lifting my head, and kissed her.. "You were the one who was wonderful, my darling.."

2,996 Words

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