Samantha Makes Skipper a Man

This is a continuation of the stories of my sexual encounters and a follow on from my story 'At the hands of Sam'.

I had been 18 for almost a year now, but still hadn't done more than received that wonderful handjob from Samantha at work.

The weekend was coming and it was also the plan to go for a few drinks with people from work as a lady from the shoe department was retiring. As Friday night approached, I began thinking, hoping I would be able to pull in the nightclub and hopefully lose my cherry. This was something I hoped for every night I went out!

The night began with a meal at a local restaurant, and then off out for some drinks, with the party splitting up into some smaller groups as the night went on. If truth be told, I wasn't having a great time, town was quiet, and it just wasn't a great night out. But then things took an unexpected, but very welcome turn for the better.

I was coming out of the toilets, when I felt a hand grab mine and pull me to the side,

"Hey there sexy!" Sam said to me.

Sam was here! When did that happen? What? How? I was confused at first and then remembered that she was out with some friends and said she may bump into everyone from work. It certainly made my night improve seeing her. She was wearing a short red dress, it's lightweight, silky material clinging to every curve of her delicious body. It was low cut, and her fantastic looking cleavage was well exposed, and I didn't think she was wearing a bra as I was sure I could see the outlines of her nipples through the fabric.

"I said Hey Sexy!" Sam yelled at me above the music, "Are you getting a good look at my tits? Hahaha."

"Sorry," I yelled back, "they, I mean you look great, it's great to see you."

Sam smiled at me and pressed me against the wall with her body, "You look pretty good yourself honey, and you smell amazing too."

Sam laughed and pulled back. We chatted about our respective nights out, and then Sam told me she thought we should each do a runner. She then suggested something else, something that set my heart racing. She said we could go back to hers for a few drinks! Well, I wasn't going to pass that up now, was I?

So Sam suggested I tell the works lot that I wasn't feeling well and was going to head home in a taxi. Meanwhile, she told her friends she was moving on to the next pub with her work colleagues, and told her work colleagues the opposite.

We met out front and were soon in a taxi for the short journey to her house.

Once inside, Sam got straight to the point.

"OK honey, I have no intention of sitting having a glass of wine with you. Follow me." She took me by the hand and led me upstairs to the bedroom. My cock stiffened in my jeans as I walked behind her, watching her hips sway and her firm arse in front of me.

We reached the bedroom and she kissed me hard, her lips open, her tongue pushing into my mouth and exploring. I responded in kind as I felt Sam's hand reach down and stroke my cock through my jeans.

"Mmm, I have wanted this thing again ever since that day at work," she sighed and then took a step back. "Undress for me baby, take it all off and lay on the bed."

I did as I was told, nervous, but aroused beyond belief. Sam stood watching as I first removed my shirt, then my shoes and socks. I unbuttoned my jeans and slid them down.

Finally removing my boxers, my cock painfully erect, and springing into view, pointing straight towards Sam.

"Oh fuck baby!" Sam gasped, "get on the bed and stroke that beautiful cock for me."

I did as asked, and as I slowly pumped my fist, watched as Sam slowly slipped the straps of her thin dress from her shoulders and let it fall to the floor. It was all I could do not to pop there and then. As I had thought, she wasn't wearing a bra, her big tits, firm and juicy, nipples rock hard and sticking out. She had on a tiny pair of red lacey panties, and some black hold up stockings, and red heels. She nibbled her finger tip, before her hand traced it's way down her neck, across her breasts and down her toned stomach, before slipping between her legs and touching herself through the thin material of her panties.

"God I am so wet right now, watching you wanking that stiff young cock for me," Sam said as she walked towards the bed.

She climbed up and knelt between my legs as she pushed them wider apart.

"Keep going," she whispered as she squeezed her breasts and pulled on her stiff nipples, moaning softly.

I wanked slowly as I watched this beautiful older woman play with her tits in front of me.

Sam reached out and pushed my hand away, taking over. I groaned as she stroked my cock slowly up and down.

"Mmm baby, so hard for me," she said as she leant forward, looking me in the eyes, "good enough to eat"

With that Sam dipped her head and gave a long slow lick from my heavy balls, up the shaft to the swollen tip. I groaned loudly, my cock twitching at this new found experience. Moments later, after a few more licks, I groaned again as Sam's full lips engulfed the head of my cock, and she drew me deeper into her mouth. Her head moved slowly up and down as she sucked me, and my hand reached down, caressing the back of her neck. Then it happened.

"oh fuck!" I cried out as my balls tightened, and I felt my cock swell. A split second later my cock twitched again, as the first shot of cum left me. Sam moaned around my pulsing dick as I filled her mouth. I could see her swallowing, taking it all, but a small amount dripped from her lips as she finally released my cock from her mouth.

"Jeesus Christ! Already?" she said in a despairing tone.

"I'm sorry," I replied "it's just, it's... That's the first time that..."

Sam cut me off "Wait! That the first time you've had your cock sucked? Oh fuck, you're a virgin aren't you?! Mmm that's so fucking hot. Well young man, that's OK then. Fuck, I am going to pop your cherry, and seeing as how your cock is still... rock.... fucking..... hard mmmm"

Sam moved up the bed, straddling me, grinding herself against my cock as she leant down and kissed me. I could taste myself on her lips and tongue.

Sam pulled back and held my head gently,

"Dont worry, this is going to be amazing. I can't believe I have been masturbating all these weeks thinking about fucking a virgin! Oh I am so fucking wet for you. Can you feel it through my panties against your dick?"

My cock twitched at her words, she had been touching herself whilst thinking about me! I could indeed feel her wetness, and the heat from her pussy as she moved her pussy against my shaft.

"Yes Sam, I think I can," I reply "it feels so hot too!"

"Just wait until you are fucking me, then you will feel how hot and wet I am honey" Sam said, her breathing heavy.

Sam lifted herself up a bit, kneeling over me, and pulled her panties aside, revealing a smooth shaven pussy. I had seen plenty in magazines and in porn films, but this was different. In reality, her pussy was much better than those. It looked so soft, the skin a deeper shade of pink than the surrounding area. Her pussy lips were like the wings of a butterfly, parted slightly revealing a silk like, darker pink shade, glistening with moisture.

Sam held my cock by the base, positioning it against her pussy lips, rubbing herself using the head of my cock. Slowly, she lowered herself down, and I watched as my cock parted those lips, and the tip was enveloped in a heat I couldn't describe, and then Sam threw her head back and groaned loudly as she sank down the length of my Shaft and paused.

"Oh fucking hell honey, your cock feels so good. I haven't had an 18 year old cock since I was younger, and I have NEVER fucked a virgin before. This is so fucking hot. I feel like I am going to cum already. Now, let me do the work, and you do as I say. I am going to ride this cock so hard, but you must promise not to cum in me. Tell me when you are getting close. I don't think my husband would be pleased! But there is no way your first time should involve a condom" Sam told me.

My eyes widened

"Wait, what? You're married? We shouldn't do this!" I exclaimed "what if he finds out?"

Sam ground her hips down on me, I groaned, I couldn't help it.

"Sssh," Sam whispered, "he won't find out from me. He is away on a golf trip. And you don't want me to stop do you? You don't want this to stop do you?"

Sam started raising herself on my cock, then sliding back down. I had never felt such pleasure, and I looked down between her legs to see her pussy sliding up and down, my shaft glistening with her juices, her pussy lips dragging along the length of my cock as she moved up, then down.

"Oh fuck no! Don't stop, please don't stop!" I begged as Sam quickened her pace slightly. She rode me up and down, up and down, hands on my chest. Every now and again she would rotate her hips a bit, or lean forward, or lean back changing the angle. I could feel my cock touching different areas of her pussy as she did. Fuck did it feel good.

Sams pace quickened again, she took my hands and placed them on her hips, and told me to pull her down onto my cock. I did, and I started thrusting my hips up, doing what seemed to come naturally, even though this was my first time.

"Oh yes baby, fuck me like that!" Sam cried out, "thrust that hard young cock into me!"

Sam leant further forward, kissed me hard, and then pulled back again. This time offering me her gorgeous beasts.

"Suck my nipples baby, I'm getting close." Sam groaned.

I flicked a tongue over one erect nipple, then the other, before fastening my mouth over one and sucking hard. Her skin tasted amazing, fragrant and slightly salty with the sweat from her riding me.

"Yes baby, that's it, fuck me. Suck my tits as you fuck me! I am going....to.......oh fuck! I'm cumming!". Sam screamed so loud I thought the neighbours must be hearing her.

The thing was, she was riding me so hard and fast, my cock pounding in and out of her, that I had lost all control, and realised I was about to cum.

"Sam! I'm going to cum!" I yelled, trying to stop and pull out.

"Oh shit! Don't stop, keep fucking me. Give me that cum! Shoot your hot load in my cunt!" Sam slammed herself down hard and moaned, her pussy tightening around my cock, as she reached back and squeezed my balls.

My cock erupted, shooting what felt like jet after jet of my cum deep inside her spasming pussy.

We lay together in ecstasy for a few minutes. We chatted and made small talk, before Sam made it very clear that what had happened was just sex, nothing more, and wouldn't, and couldn't happen again.

Sam said I would have to leave as she couldn't risk her neighbours seeing me leave in the morning. She called me a taxi and ushered me out quietly when it arrived.

What a night. It left a memory so strong it's seared into my brain, and still gets me rock hard when I recall my first time.