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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, canlı bahis 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.

No time to admire his physic I was only interested in getting at his cock. I unbuckled his belt and flipped the button before unzipping his pants, Sliding his slacks down, leaving his boxers bahis siteleri in place. I regained a little composure and decided to tease him a little. I grabbed his bum and caressed it placing little kisses on his tummy and around the waistband of his boxers.

Enough of this teasing down to the crux of the matter. I slowly eased his boxers down exposing the base of his cock, it appeared thicker than Pete’s. I placed a little kiss on it and eased his boxers down further expecting his cock to leap out. I eased his boxers down a little further, and further and further. Jesus what had he got here? Without much ado I pulled his boxers right down past his knees. His cock leapt out springing upwards.

My eyes opened wide at the sight that greeted me, “Oh my God,” I managed as I stared in awe at the size of his dick.

Steve was looking at my reaction, “Sorry Jackie.” He apologised smiling, he had obviously seen this reaction before

I had never considered the male organ could be this large, believing Peter’s to be how they came. I couldn’t take my eyes from it. Almost scared to touch it, as it was pointing directly at my mouth. It seemed the obvious thing to do was use it on him. Slowly I moved forward and placed a kiss right on the end of his cock, it twitched in response.

“Mmmmmm,” He moaned

Taking Pete in my mouth had been alot easier than Steve as I soon discovered. My mouth struggled to accommodate his girth, I reached up and took him in my hand although I could only get about two thirds of the way around. I kissed up and down his shaft making him groan. Returning to the head I could get a couple of inches into my mouth, I coated the top of his cock in saliva and admired my work. I had always considered I gave a decent blow job.

Steve placed his hands on my shoulders and lifted me up onto the bed, I glanced down and saw his cock pointing towards my crutch, my wanton willing very wet crotch. Oh how I wanted him, to feel his cock inside me, his huge balls banging against my bum. I needed shagging and no mistake about it I needed shagging now. Steve moved forward holding his cock in one hand he rubbed his knob end along my wet slit. I opened my legs and lifted them towards my chest. His knob end entered my willing pussy, slowly he began to move into me.

Then we hit a problem, the size of his cock was stretching me unbelievably, I had never experienced anything like it, “Aaaaaaaah,” I screamed, “Stop! stop please stop!” Steve was full of apologies and stopped his advances. My pussy felt completely full, in fact overfull. I looked down between my legs and could see what must have been eight inches of his cock not in me, “Take it out,” I ordered, “For Gods sake, take it out.”

“Sorry Jackie,” He apologised again and slowly, obviously reluctantly withdrew his cock from me. I watched as he did so, surprised there was no blood on it. I felt relief as he withdrew completely.

There were tears in my eyes and I whispered, “Sorry.” Not knowing what reaction to expect.

“It’s me that’s sorry for subjecting you too…”

“Don’t be silly,” I stifled any further words with a kiss.

Steve lifted me up and laid me on the bed placing my head on the pillow, he slipped alongside me pulling the duvet over us. “Will you stay?” He asked almost pleading.

I was just relaxing again and getting that wonderful contented feeling after all I had just had the most intense orgasms of my life, I kissed him passionately before putting my head on his chest. I must have been asleep in seconds, a deep satisfied sleep..

When I opened my eyes it was morning, well I surmised it was morning because sunlight was streaming through the curtains. I gathered my thoughts and viewed my whereabouts. I analysed the situation, before I turned hopeful of finding Steve lying next to me. I was surprised to find myself alone. I heard presumably Steve moving about in the kitchen, lying on my back I took stock. I decided I was happy with my decision to spend the night here.

My mind quickly went back to the sexual activity of last night, or the lack of it you may say. I wondered if I had dreamt it, did men have cocks of that size or was it just a dream? My hand went down between my legs my pussy lips were puffy. I slipped a finger inside and discovered I was slightly sore. Moving my finger slowly my clit began to stir, this occurrence usually took much longer, I also found myself becoming aroused. It was then a sense of panic took over me. I had to face Steve and was unsure of what approach I should take?

As I was naked I needed to discover some of my cloths, I slipped out of bed and found my thong on the floor. Turning them the right way round I noticed the gusset was distinctly damp. Oh well, the only pair available so I slipped them on. My dress was in a heap also on the floor. Now where was my bra? Not to be found anywhere, well my boobs were firm enough to go without. I pulled my dress on and took a look in the mirror. My hair was a mess and my handbag could be anywhere, so no make up or hair brush. I scrunched my hair and it looked half decent. My dress looked really out of place. it looked as if I was ready to run home, the bahis şirketleri walk of shame. Not the impression I wished to give. I noticed Steve’s shirt was on the chair. I took off my dress and slipped on his shirt. The smell of his cologne almost sent my head spinning. I glanced in the mirror, I looked pretty raunchy if say so myself. I flipped another button open to reveal a bit more cleavage. Was I sending out the right message? Time to find out, I walked into the lounge and through to the kitchen.

Steve noticed me immediately, “Good Morning sleep well?”

“Very well thanks,” I was at ease almost at once.

“Coffee or tea?”

“Tea please.”

“Take a seat,” He gave me the once over and motioned for me to sit at the breakfast bar. I knew if I sat on the stool his shirt wouldn’t cover much of my modesty, he must have got an eyeful of my panty covered crutch has I sat down. He poured my tea and handed me a fresh croissant. After another cup of tea we were chatting away like old friends.

Steve broached the subject that was obviously on both our minds, “Jackie I’m so sorry about last night.”

“Don’t be silly.”

“No, no I plied you with drink and tried to take advantage.”

“I came here of my own free will, and didn’t put up a fight did I?”

“Well no but I feel…”

“Don’t feel anything,” I attempted to placate him.

“Well I do.”

“I expect you feel horny,” I could have shot myself for coming out with that stupid comment.

“Well now you mention it,” There was a big grin on his face, I blushed profusely not for the first time in our short relationship

“Sorry,” He apologised again, “I am sorry if I errr shall we say surprised you.”

“You did that alright,” I agreed, “In more ways than one.”


“I’m not very experienced,” I confessed, “If you know what I mean.”

“You weren’t a virgin?” Steve looked quizzically towards me.

“No I wasn’t,” I said firmly, “Just not very experienced,” I elaborated, “I had a boyfriend for two years but…”

“But sex wasn’t all that good I’m guessing?”

“I thought it was, we were both virgins.”

“Oh dear.”

“What do you mean, I loved him?”

“That’s as maybe but..”

“But what?”

“Well a beautiful woman needs and experienced lover.”

“Oh do they?” I tried not to show offence, he had called me a woman, the first person ever.

“You appeared to enjoy my early attentions last night.” He went on.

Again I blushed, I also felt my pussy beginning to tingle as I recalled vividly his attentions of the previous night. Once again my mouth appeared to have a mind of it’s own, “I cannot deny that,” I blurted out much to Steve’s amusement, “A shame we didn’t finish things off.”

“Can we try again?” He asked, almost begging I thought.

“I’m surprised you want to.”

“Oh Jackie, I want to very much and I don’t want to offend you.”

“When do you suggest we continue our relationship?” I asked with a girlish grin

Steve moved to me by the breakfast bar, he slipped his arms around me and said, “No time like the present. His hands cupped both my breasts, my nipples instantly responded, giving him my answer. He grabbed my hand and led me once again to the bedroom.

I turned and kissed him, “You get in bed I’ll freshen up a little,” I headed into the bathroom.

My mind was in turmoil, every inch of my body wanted sex and more of the treatment Steve had served up previously. But I was concerned that I had not imagined the size of his dick. The cock I couldn’t handle last night and that after a few drinks, what would it be like in the cold light of day.

I slipped into bed next to Steve, his shirt lasted about ten seconds. His kisses were urgent and wanting, his hand slipped into my thong. “Mmmmm,” He sighed as he discovered my wet pussy. Again his expert touch had me squirming, my clitty felt huge as he gentle played with her. He kissed down my body slipping my thong off a he approached my quim. He teased all around my pussy I was almost begging for him to lick me. Thankfully he couldn’t resist it for long.

“Yeeeeesssss,” I let out as his tongue found my clitty and worked me over brilliantly. “Jesus that’s it ahhhhhhh.” I came unashamedly with his expert tonguing

I recovered and now it was my turn to discover if I had been dreaming or was his cock really as big as I thought. I kissed down his chest slowly taking the duvet with me. Before I got to his navel I encountered the head of his cock. I pulled the duvet off him and just stared at his monster of a cock.

“That’s fucking huge,” All I could say. I didn’t usually swear but it was the only comment I could think of. I looked at his face a broad smile across is lips. His cock gave a twitch as if it was begging me for attention. He we go, I thought and placed my hand around him, this confirmed last nights findings. There must have been a two inch gap between my thumb and index finger. My mouth had to be wide and I mean wide open to accommodate him. Any of my misgivings soon disappeared and I went for broke. I gave it my best go, and after a couple of minutes of sucking, kissing and licking his cock all over I heard him groan. I decided to lick his balls. I had never tried this before and was more than impressed with the moaning reaction it produced. Steve’s balls were atleast twice the size of Pete’s.

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