The First Date
My name is Jackie, I'm now twenty nine years old, however my story begins when I was just turned eighteen. I was always a skinny girl and preferred sporting activities to dating boys, probably because I didn't start to mature until I was just over sixteen. Yeah I was pretty flat chested, and could have passed for a smallish boy until then. When my body changes began I kept my petite stature, I did however developed a nice pair of breasts, and thankfully my bum filled out to become most attractive, especially in tight jeans. Naturally boys began to take an interest. At first I shunned any advances, but a lad called Pete won me over and I agreed to go out on a date. We were both pretty naive, and a quick kiss after going to the cinema was all we managed on our first date. But that kiss sent a shiver down my body that I will never forget. It was of course the start of me becoming a woman. I also discovered the delights of masturbation, my fingers created fantastic sensations that racked my body on a very regular basis, sometimes four or five times a day.
Pete made tentative advancements and over the next couple of months we got more and more adventurous, from kissing to heavier petting, we were both learning as we went. Pete got his hands inside my panties one night, it was a bit awkward and not a great experience for me although he seemed to enjoy his efforts. A week later we had my parents house to ourselves and I took the plunge and got his cock out of his pants. It was hard and appeared very big to me. It seemed only natural to move my hand up and down it and after a few strokes he groaned and shot his load. I was fascinated and felt I needed to take things further. Pete was walking on air, a permanent smile on his face. A month later we had had full sex half a dozen times and considered we were becoming good at it. Pete didn't come quite so quickly, I didn't reach a climax during sex but would certainly make up for it in my bed later in the evening.
Just before my nineteenth birthday Pete and I fell out. After pledging our undying love for each other after sex one evening just a short while ago he told me he didn't love me anymore and wanted to move on. To say I was devastated was an understatement, heartbroken, my life didn't seem worth living, I cried alot. I considered begging him to reconsider. My Manageress at work realised I wasn't myself and I opened up to her over a drink after work. Her words of wisdom telling me to move on, I was nice looking, fabulous figure, she tried to cheer me up, it didn't work to well. But I did think about what she had said later and decided to move on from Pete. Pete who incidentally was going out with a right little tramp from the local council estate.
Anyway decision made, I was going to move on. I concentrated on work and bought myself a whole new wardrobe. Men didn't figure in my plans I'd been hurt and didn't fancy going down that path again. In fairness a couple of the girls at work became good friends and we started going out, just for a drink at first then someone suggested a nightclub. Sure we all got plenty of male attention but kept them all at arms length. Apart from one night when Kathy had sex with a guy she fancied we had a giggle about it when she described how small the guys willy was, and how quickly he finished.
After six or seven months of having a great time I was becoming restless, I needed a boyfriend. I discussed my feelings with my two mates and fortunately they both had similar feelings, so we made a pact. We wouldn't go out on the pull, we'd just see what happened, who comes along. Well our first two nights out after our pact only produced a string of idiots trying it on after too many drinks. None of us appreciated a hand thrust up our skirts in the middle of the dance floor. On our third night out Tracey pulled a bit of a catch, Kathy and I were both slightly jealous if the truth was told. Kathy was dancing with her tall good looking guy when I spotted a chap at the bar. I know it's a well used cliché, but our eyes meet across a fairly crowded room. Ten minutes later he had brought me a drink and we were chatting, a couple of dances and another drink unfortunately the club was closing. Kathy and some bloke came over to check if I was okay. It was obvious they were going to get it together and didn't want my company for what they had got planned. Steve came to my rescue offering me a lift I accepted a little too quickly. I regretted it immediately not wishing to appear easy. Steve smiled and was the perfect gentleman, we left the club with Kathy and Brett. I watched as they walked to his car hand in hand. Steve escorted me to his car, a very nice top of the range BMW, pure luxury.
"Where too madam?" He asked. I was lost for a reply not wishing to say the nearest bedroom and appear as if I was gagging for it. Again he put me at ease, "Well I fancy a bite to eat."
"Sounds good," I managed a sensible reply this time.
"Italian okay?"
"Mmmmmm." Ten minutes later we arrived at a very suave Italian restaurant, we were shown to a window table by a waitress. The next couple of hours flew by, everything was absolutely perfect, the food, the company, the wine, everything, absolutely everything Now time to leave, and move on to presumably the next stage. Steve opened the car door for me and ushered me inside.
"Night cap?" He asked
"Mmmmmmm that would be nice," Again I was too eager.
"Your place or mine?"
There was only one answer to that question, my parents wouldn't have been to impressed with me arriving home at this hour with a stranger in tow. "Yours," I ventured, "But just a nightcap."
"Of course, what kind of chap do you think I am?"
"That's a leading question isn't it?" We both laughed, a couple of minutes later we were in a private underground car park. We took a lift from the car park to the penthouse apartment. "Wow this is nice," I said admiring the view over the city from his very impressive flat.
"Glad you like it." Steve handed me a glass of chilled white wine.
"Thanks." I looked at him and knew when he made his move I would not resist his advances, if I was honest I couldn't wait. I had a tingling in my pussy I hadn't felt for several months.
Jackie wanted sex, and Jackie wanted it badly, hard and fast, and I wanted with this gorgeous man. I looked at Steve, estimated him to be twenty four or five. He caught me looking, he didn't say a word just moved towards me and took me in his arms. Our lips met, our tongues entwined and danced together. If I had any resistance, and it was a big if, it was rapidly disappearing, Steve moved me towards the bedroom. An equally impressive bedroom with a huge bed.
Our lips never left one another's until he gently sat me on the edge of the bed, he leant forward and we were kissing again. This time he kissed down my neck, he nibbled my ear. He moved towards my breasts. I sighed deeply as he slipped my dress from my shoulders, expert fingers unclipped my bra I did not resist.
His lips found my embarrassingly hard nipples, Steve was so gentle and taking his time. Unlike Pete who was rough and urgent in all he did concerning sex. My dress was now down to my waist and had ridden high up my thighs, I suspected my panties were in full view.
I was used to Pete diving straight in, heading right for my pussy. Steve was just the opposite, kissing down my tummy then returning to my tits. I groaned in appreciation as he teased my nipples again, occasionally biting them gently with his teeth. His hands ran up my thighs stroking gently as he went higher and higher. He arrived at the crutch of my thong, if it was damp I wouldn't have been surprised or embarrassed Steve had me swooning.
I had never been treated like this and I loved it. Steve's fingers were working around the crutch of my thong gently turning me on even more, if that was possible. After a few minutes of this treatment my breathing was heavy. My backside was moving attempting to get my pussy onto his fingers, he teased all around my pussy. God there was no sense of urgency in his actions, just teasing. I moaned when he got his finger into the back of my thong and gave a little pull causing it to rub against my clit.
Another surprise came next when Steve moved down and began to kiss my inner thighs, moving upwards slowly towards his target. Again expertly he pulled my thong to one side. This time his kisses found my wet pussy, he moaned his appreciation as he ran his tongue along my pussy lips. My bum was certainly off the bed at this stage.
Pete had attempted oral sex on me but I have to admit his technique didn't do much for me. This was a completely different ball game, I had never felt such sensations. The feelings coming from between my legs was controlling every inch of my body and mind. Steve found my clitty, she had conveniently come out to play and that was it, I had my first orgasm induced by someone other than myself.
Unashamedly I grabbed his head and ground my crutch hard onto his lashing tongue, my orgasm intensified. Steve grabbed my legs and pushed them upwards towards my chest, this exposed my pussy fully to him.
Did I care? Was I embarrassed? Not one iota. Steve somewhat mercilessly worked my clit, he slipped a finger into my wet pussy, my orgasm went on and on. I knew I was screaming loudly but didn't care.
I felt my orgasm subsiding and I began to relax when Steve attacked my clitty with renewed vigour, my subsiding orgasm reared its head again taking me back to the dizzy heights once more. Jesus could I take this anymore? Another orgasm racked my body and mind. I was just at the top of my orgasm when Steve slipped his little finger up my bum. This new sensation enhanced my pleasure beyond belief, I may have even passed out for a few moments, passed out through the sheer pleasure this man had given me.
I had no idea how long he had performed on me. I was regaining my senses when it dawned on me I had been totally selfish. I intended to make amends and attacked his shirt unbuttoning it somewhat expertly.
