My First Proper Date

I thought I would try and tell the story of my first "proper" date.

How do I begin? Well, I suppose I should tell you a bit about myself first. I am 22 years old and just recently graduated from my local college and moved to the big city for my first real job. I am fairly shy and reserved which is probably due to a pretty strict upbringing. My mum and I lived with my grandparents since my Dad left us when I was 8. So I was glad to be able to start living my life away from my family. I have long red hair and stand about 5'5.

I wasn't a virgin, I had lost that to my college boyfriend a few years ago. We had broken up half way through our final year. He was romantic, tried very hard to please me but well he never really set my heart going. To be fair he never had a chance. I just never really fancied boys. Men on the other hand, much older men was a different story.

I had always found much older men attractive for as long as I had noticed the opposite sex. At college I had stumbled across a couple of sites of old men and teenage girls having sex and it's the only time I had ever managed to get myself off. It was just fantasy of course. Dating a much older man would have been unthinkable. For a start my family would have killed me.

But I was in the big city now, away from anyone who knew me, free to do what I wanted.

I woke up one Saturday morning slightly hungover. A colleague had set me up on a blind date the night before. He was a nice enough boy but as you will have guessed he was not my type. The wine had made the evening tolerable albeit a rather short and fruitless evening.

I grabbed myself a cup of coffee and got back into bed. I pulled the laptop up from the side of the bed and sipped my coffee waiting for it to finish loading. I needed to find a proper man. I wanted a relationship.

I had realised the internet was my best bet in finding the type of man I was looking for. Well I had after spending an evening fluttering my eyelashes at a fifty year old man across the bar only for him to come over and ask how much!

I opened the internet and started typing. It was not as easy as you would think. Most sites are for girls looking for sugar daddies which was something that wasn't quite right for me. I often get asked why then if it's not for the money. I suppose I like the power and control older men can radiate. There is also something wickedly dirty about giving yourself to someone much older and less attractive. After a few searches I found an interesting looking dating site for those looking for an age difference. I messaged a couple of the men and waited.

The responses were not great. Some were only interested in whether I would send them nudes. Others were unbelievably grateful that a young women might be interested.

One responses caught my eye. It was from an Adam Jenkins (well that's what I will call him for the purposes of the story), he appeared arrogant and sexist. So I did what every self-respecting women should not do and emailed him back. We exchanged a couple more emails and agreed to meet at a fancy French restaurant in the west end on Friday night.

I had been on dates before but not to anywhere posh. Besides did they even count as dates if they were only with boys? I couldn't remember ever feeling this nervous about a date before, I even took the day off work to get ready!

I was regretting the second glass of wine that I had while getting ready, as I balanced on my highest heels getting out of the taxi.

My date was already seated at a table near the door as I entered. He looked mid-fifties and had a grey beard and thinning hair. He was in a very expensive looking smart suit.

He signalled me over to the table. I was aware he was looking me up and down as I approached.

"Jessica?" he asked standing up.

"Mr Jenkins," I replied with a smile.

Should I have called him Adam? I had always been taught to refer to seniors formally and with respect. What was I thinking though? I was on a date with the man. Why were all these crazy thoughts going through my head? He must think I'm an idiot as I stand here with this stupid grin on my face.

"Please sit," he instructed.

I pulled the hem of my tight black dress down aware it was riding up to expose my stocking tops as I sat.

"You look lovely," he said as I noticed him staring down my cleavage.

"Thank you", I mouthed as I blushed at his compliment.

The waiter soon arrived to take our orders. I scanned the menu again as Mr Jenkins gave his order. I had no idea what half the things on the menu were, let alone how to pronounce them.

"The same for the lady," he told the waiter.

I had been five the last time someone had ordered for me. Part of me thought I should be offended but it felt nice for someone to take control and I heard myself quietly say thank you.

He talked a lot through dinner mainly about himself, his travels and his company. I felt in my 22 years of life I had little to add to the conversation. My life seemed boring compared to his. My few attempts at joining the conversation sounded embarrassingly pathetic to my own ears. I sat there staring into his eyes, smiling and nodding like the polite sophisticated dinner companion I was trying to be and not the silly girl at the grown up table I felt like.

When the bill came I reached for my purse. He shot me an offended look and firmly took the bill.

"Thank you Mr Jenkins for a wonderful dinner," I smiled.

Was I really still calling my date by his surname? I was sure he would be glad to be rid of his witless guest. You would never have guessed I had graduated with honours by tonight's performance.

"You are most welcome my dear," he replied. "My apartment is just round the corner why don't you come back for a night cap and you can thank me properly."

I was shocked as my companion had been a perfect gentleman all evening, well apart from staring at my breasts throughout dinner. I didn't want my first proper date to end, however, and just nodded.

"Excellent," he replied.

I took his arm as we made the short walk to his apartment. He smelled musky with a hint of tobacco. The concierge couldn't take his eyes off us as we entered the building. I turned to look at Mr Jenkins to see a smug proud look on his face as he smiled knowingly towards the concierge. His hand moved from the small of my back to my firm bottom as he let the concierge know I was his. There was something about the fact that here I was, a beautiful young women, giving myself to this old unattractive man. I squeezed his arm tighter and rested my head on his shoulder as he guided me into the lift.

I followed him into his apartment, my heart thumping in my chest. It smelled like its owner. He took off his jacket and sat himself down in the sat in the middle of one of those corner sofas.

"There is some scotch in the kitchen," he instructed. "Get me a glass and come and join me."

I found the glasses and scotch in the small kitchen. I filed the glass half full and quickly downed it before refilling the glass for him.

"You are an attractive young women," I told myself. "You want him and he wants you. You can do this."

I took a deep breath and went back into the lounge.

He patted his left knee as I handed him his glass. As I sat on his knee, I went to pull the hem down of my dress again, from exposing my stocking tops. I was immediately greeted with a light slap of my hand and a stern look. I looked down embarrassed about being chided. He lifted his chin with his hand and pushed his mouth towards mine. His beard tickled as he crushed his mouth against mine. My lips parted letting his tongue explore my mouth. He pulled me closer towards him and I could feel a hard lump under my bottom.

His hand moved from my chin down my neck and into the top of my dress. He groped my large firm breast as he roughly kissed me. His other hand went to the back of my neck under my long red hair. I heard the sound of a zip followed by the cold air on my chest as the top of my dress fell down. Unhindered by my dress his other hand moved into my bra exposing my left breast and cupping it. His thumb played with my nipple as he continued to kiss me.

His hand moved to my leg moving up and down my thigh before coming to rest at my stocking tops. Slowly his hand began to move upwards under my dress and to my knickers. He pushed his fingers under the elastic and found my slit. I let out a loud gasp. His calloused finger rubbed up and down my wet slip before it started to worm its way into my tight pussy. I was struggling for breath.

There was a hungry look on his face as he broke the kiss.

"Now my dear were you not going to thank me." It was more of a command than a question.

Taking his meaning I stood up. My dress slipped down my stocking covered legs to the floor. I stepped out of it and reached behind my back and unclasped my bra which also fell to the floor. I stood there in front of him in only my panties, stockings and heels.

I got down onto my knees. I slowly unzipped his trousers and gently slipped my soft hand into his trousers. From my limited experience of men I expected to find him rock hard and ready to burst. I was slightly disappointed to find him only semi hard. He must have been about 4 inches which was what my previous boyfriend was. I held him softly in my hands and gave his dick a long lick. I looked up at his expectant face before slowly taking him between my soft lips. I was pleased to hear him moan as I took him fully in my mouth. I could feel him grow and get harder as I sucked on his cock. It wasn't long before he was fully erect. I took him out of my mouth and admired my work. He was now a good two inches longer than my ex.

He stood up and grabbed my upper arm pulling me up onto my feet. He grabbed my hips and pulled me towards him. His bent and wrapped his mouth round my breast, sucking roughly. I moaned softly feeling his tongue over my nipple. He stood up and held my face in one wrinkled hand.

"Now my dear I should warn you," he said. "I've had a stressful week and I'm going to take the brunt of my frustrations out on that fine body of yours."

I stood in shock, I really was just a piece of meat to the man. I should have been offended but I had never been so turned on in my life.

"I'm yours," I replied.

"Lie down," he barked.

I lay down on the sofa bringing my heels towards my bottom and obediently I opened my legs for him.

He looked down at me as he took another drink of his whisky. Placing the glass down he then scrambled on top of me. The weight of his body pushing me into the sofa.

His wrinkled hands grabbed the gusset of my knickers and pulled them roughly to the side. I felt his cock wet, with my own saliva, move across to make its way to my entrance as he lined himself up. I let out a loud moan as he roughly pushed into my tight pussy in one long thrust. He was much bigger than I was used to and I wrapped my stocking covered legs round him, my heels clicking together as I locked my ankles behind his back.

He slammed into me again. I was struggling to get my breath as he pulled back before slamming hard into me. His balls bouncing off my bottom. I turned my head to the other side and could see our reflection on the side of a mirrored cabinet. I could see his saggy arse moving up and down as he ploughed into me again and again. I moved my legs down to the bed as he found his rhythm.

He stopped and leaned up taking each of my legs. He pulled them up into his shoulder. I bit my lip, as though it was uncomfortable, I didn't want him to know I wasn't a flexible young sex goddess.

He pushed forward again entering me roughly. My legs were pushed up towards my face. It was uncomfortable but he was in so so deep and he felt so good.

His face was red and covered in sweat as he pounded into me even harder than before. The image of him against my firm young body was incredible. "Mr Jenkins," I moaned. There was something dirty about calling him by his surname.

"Oh! Mr Jenkins," I moaned again. "Use me!"

He seemed to like that as he picked up his speed. He was fucking me as hard as he could now.

I cried out in pain as his hand behind my shoulder grabbed a handful of my long red hair and pulled.

My pain was mixed with excitement though and I felt myself getting close. His breathing was getting ragged and his strokes were losing rhythm. I moved my legs off his shoulder but kept them in the air wide apart. He let out a load moan and I felt him burst inside me. He collapsed on top of me, winding me, as his hot sperm slowly dripped out of me. I wrapped my legs round him and squeezed wanting to keep him as close as possible.