Family Friend

Hope you enjoy the story and hope to hear what you thought.

This story is about a guy called jack who finally got his first taste of a woman at the age of 22, and with a woman 25 years is senior.

Let me start by saying that it is a mystery how someone as good looking as me is still a virgin at 22. That might sound a little arrogant, but its the truth and I am told this on a regular basis by many women, not just by me mother. For some reason, I have gained this reputation for being some kind of Casanova with the ladies and I don't think any one would believe the truth about my virginity. My main problem is that I don't think I will be able to measure up in the bedroom department and this fear is not helped by the fact that I think I'm a little small downstairs at just under 6 inches.

Every year I would tell myself that this would be my year and I would finally pluck up the courage and just go for it. At this point, I didn't even care with whom, I just wanted to be able to experience what it felt like to be with a woman.

I knew I had the house to myself for the weekend, cause my parents were still away on holiday, so this was my perfect opportunity to just go out with my friends to a club, get drunk and find someone to bring home and just get it over with. I know it sounds romantic, but I really don't care anymore.

Once at the club, we started hitting back the tequilas like there was no tomorrow, In my case it was for courage. After about an hour I’d had enough drink to loosen myself up and was ready to show my moves on the dance floor. Straight away this cute little brunette caught my eye and we hooked up right there in a scene which resembled the one in Dirty Dancing, this however was much more steamier. This girl was all over me, she was like an untamed tiger clawing at her prey. I thought she was going to rape me right there on the dance floor. “Lets go to the bathroom”, she shouted in my ear.

You don't have to tell me twice, its finally going to happen I was thinking.

As we made our way through the packed club, I’d just realised that I hadn't brought the condoms with me. Maybe she wouldn't care, she was too out of it to even know.

After what seemed like an eternity, we finally made our way to the ladies bathroom, she leading me into the nearest un used cubicle, looking the door firmly shut behind us. We started kissing wildly, her hands immediately going for my belt buckle as my hands grabbed her ass pulling her firmly to my fully erect waiting cock. My belt was off in a second, followed by her hand inside my pants. This was it, would she be disgusted by my small size I was thinking. Finally she grasped it and let out a mmm sound which really boosted my confidence. Maybe I wasn't as small as I thought, she seemed to be enjoying herself as she jacked me off, still kissing me, but her lips were now firmly planted on my neck. I was really getting into this and knew I was about to fuck this wild woman, when I heard the music go off in the club and voices yelling outside the cubicle.

“Police, open the door now”. Fuck I thought, what the hell is going on. I had the police screaming outside the door and this girl was still nibbling away at my neck with her hand still firmly around my cock. I pushed her away and pulled my pants back up, trying to get composed and ready to face the cops. As soon as we stepped out from the cubicle we were frisked by the cops and searched for drugs. I wasn't worried cause I knew I was clean, I never touch the stuff, well, I did smoke pot back in summer camp, but that was a long time ago. I was clean, but the girl I was with wasn’t. She had a bag full of pills with her, probably ecstasy, and she was taken away by the cops. No wonder why she was acting like a wild woman, she had been drugged up to the max.

Just my luck, just when I was about to finally get somewhere with a girl and this happens, what are the fucking odds ? I was totally gutted and felt pretty pissed on the way back to my empty house where I would spend the night all alone.

Arriving at the driveway to the house, I saw lights on in the lounge, which was strange because my parents were not due back for another 2 days. I walked through the front door a little cautious, “mum, is that you ?”. No reply, but I heard a crying sound coming from the kitchen. “Who’s there”, I shouted as I entered the kitchen.

Sitting at the kitchen table crying away was Fiona, a friend of my mother’s. “Fiona, what’s the matter”, I said, as I sat down beside her. “I’m sorry Jack, I used the key under the doormat to let myself in, I didn’t think there would be anyone in, I just wanted to be alone away from everything”.

“But why are you crying Fiona, what's happened ?” I really hated seeing this woman crying, she was one of the nicest people you could ever meet and we had always been very close. “Jack, you don't want to hear a stupid old woman’s problems, you should be out enjoying yourself”. I put my arm on her shoulder and told her, “firstly, don't ever think that your stupid and secondly you are definitely not old”. That last word got a little smile from her. “Thank you Jack , you have always been a sweet talker and you know how make a woman feel special”

“So are you going to tell me what it is that has upset you ?” “Its pretty stupid, but the reason I was so upset is because I was supposed to meet this guy for dinner at Salvo’s and the jerk didn’t show up and couldn’t even be bothered to ring me to let me know. So I came here to get a drink, since I drank my last bottle of vodka last night”.

She certainly did like to drink her Vodka. I knew this from looking at the half empty bottle on the kitchen table.

“Fiona, I’m sorry to hear that you got stood up. The guy is obviously a fucking twat to do that to such a sweet lady like you”. She returned my compliment by moving closer to me and kissed me softly on the cheek, leaving her lips touching my skin longer than a usual friendly kiss should. I figured it was just the amount of drink that she had consumed and didn’t think much of it.

“I think I should make you a coffee so you can sober up before you go back home”, I said as I rose to go to the kitchen sink. I must admit, Fiona did look different in some way tonight and you could even say she looked sexy. Id never really thought about Fiona in a sexual way before tonight, but with the amount of tequilas I’d had and the fact that I was still feeling horny from earlier on, she was looking sexier by the minute, even if she was 47 years old, the same age as my mother.

If I were to describe her, I would say she was quite pretty, short blonde hair, blue eyes, petit body with small breasts but overall very good for her age. This particular evening she was wearing a short black skirt and a white blouse which did nothing for her figure.

Turning around to ask her if she took sugar, I was slightly shocked to see that she had moved from the chair and was now sitting on the table with a seductive look on her face. “Jack, can you come over here please”. I thought for a second and went over to her. She got off the table as I approached her and met me half way, our eyes never leaving each other. We both knew what was going to happen, and we both wanted it to as we embraced each other passionately with our first of many kisses.

She smelled so sweet and tasted even better, just like a vintage wine that has matured over the years. Her hands were running through my hair as our tongues continued to play with each other, my own hands now resting firmly on her petit behind.

I broke our embrace and lifted her onto the table, positioning myself closer to her in between her legs which were now hanging either side of me. I was now in control of the situation and she realised this, which I believe turned her on even more. Her hard nipples that were piercing through her blouse were evidence of this and her lust could not be denied.

Seeing this older sexy woman in this position before me obviously had an effect on me and I don’t know what came over me but I had the urge to rip her blouse open, the buttons flying across the kitchen. She looked shocked by my action and her breathing increased slightly, but I saw the look in her eyes that told me she liked it.

She wasn’t wearing a bra underneath and her bare breasts were now in full view to my adoring eyes. They might have been quite small, but her nipples were the biggest protruding things you could ever imagine. I placed both hands on each breast and massaged her nipples with my thumb, back and forth, hardening even more to my touch. She arched her head back and sighed deeply, encouraging me to continue, but this time replacing my hands with my lips. I lay kisses around her nipples , going from breast to breast, listening to her very soft moans which turned to a groan as I sucked on her nipple. I continued milking on these beautiful things, adding a few playful bites in, which seemed to do the trick because she wrapped both hands around my neck, forcing me to carry on.

“Jack, I cant wait any longer, I need you to fuck me right now”. That was all I needed to hear. I Stepped back from her and started unbuckling my belt as fast as I possible could as she fumbled with the buttons on my shirt. My pants were around my ankles, my shirt was open and we were both pulling down her skirt and panties. This was it, I climbed onto the table, positioning myself over her naked, waiting body as she grasped a hold of my cock and guided me into my first pussy. I thought jacking off was the best feeling you could ever experience, boy was I wrong, this was amazing. Each thrust into her made us both moan in pleasure, I wanted to last a long time, but I knew I wouldn’t be able to control myself. Fiona had now wrapped both her legs around me and I was about to cum, so I started fucking her harder than before. I could tell by her moans that she was having an orgasm, or I hoped she was, and that's when I started to cum, shooting deep inside her warm body, continuing to thrust into her until I shot my last load of cum.

We both laid entwined together on top of the table until our breathing returned back to it’s normal state. “I’m sorry Fiona that I didn’t last long, its just that you made me so excited I couldn't control myself any longer”.

“What are you saying sorry for Jack ? That was the best sexual encounter of my life, Know one as ever made me cum as hard as that before. And besides, this is only the beginning for us”.

I couldn’t believe my luck, she wanted us to have sex again. Maybe next time I will receive my first blowjob.......................