Bedding a Stranger

You read about these things in Penthouse, and on the internet, but you never expect them to be real, let alone happen to you. And you sure don't expect them to happen when 6 months ago you considered yourself a lesbian. It's amazing how things change in your life – especially when a man walks into it.

6 months ago a guy shows me I could still desire men. 6 months ago half the population of the word suddenly sparked interest for me again - an interest that caused years of pent-up desires to come rushing forth. Desires love couldn't keep up with. So I started to search for relief.

My search consisted of the neighbors, co-workers, and people I stood in line in the store with – but nothing. I was confused, the last time I went after men, especially looking for sex and no attachments, I had my pick of the litter. Of course last time I'd looked I was 20 years old, a stripper, and had a body to die for. I finally realized I'd have to search a little differently this time around, so I turned to the internet.

Craig's List has a "Casual Encounters" section where desperate sex-starved people like myself can find others looking for the same thing. Although, as I discovered, not everyone's looking for the same "thing". Some want to give, others want to receive, and some want things that just made me laugh really hard. Two weeks I looked. Two weeks I scanned through listings posted without "my type" in mind. Two weeks of looking at occasional postings that might have worked – but my intellect would kick in. Are those people for real? Were the after-school specials right that every guy on the internet just wanted to rape and kill you? Could I possibly conquer my fears and shyness to actually respond if I did find something that matched me?

Then it happened. I found the post written with "my type" in mind. Some guy was looking for a girl to stimulate his mind. Minds I can stimulate very well, and with it posted in Casual Encounters, I thought he was probably eventually looking for more than just a mental stimulation.

I stared at that post for an hour. I'd go and look at other posts during that hour, but I always seemed to gravitate back to that one. Finally, I realized I was being silly – I wouldn't find another post that fit me to a tee that much. So I summoned every bit of courage I had, and replied. Hours passed and there was no answer. I figured the guy had found what he was looking for already, and forgot about it.

The next morning, I went to work just like every other day, not realizing how things would change for me that day. I checked my email to discover the guy had answered, and was apparently intrigued. We exchanged emails all day, slowly broaching the subject of sex. Finally, I threw out what I thought would be the clincher – my fan fiction. NC-17 rated stories that I thought for sure would capture his interest. I was right.

The conversation never left sex after that - each email steamier than the last. We ended that night having incredibly satisfying phone sex.

Sex by email continued the next day, and I realized I had to meet this guy. I had to see his face – to see if he was really the guy in the pictures, and to reassure myself that he didn't appear to be an ax-murderer. We met that evening in a store, pretending we really weren't there together, pretending to be anything but nervous and full of sexual tension. He really wasn't the guy in the pictures after all. He was so much more - attractive, and oozing with sexual confidence, male pride, and dominance. He was, in short, everything that turns me on in a guy.

Innocent, short meeting, but I knew I had to have him. So I pulled my stripper attitude out of mothballs – cocky, self-righteous, and downright bitchy – and set about hooking him in.

All weekend the emails continued, each one steamier than the last. Both of us trying harder with each email to make the other one squirm. All the while I'm assuming his attitude is the same as mine – covering the someone inside that wants him so bad, yet is absolutely terrified they'll get killed, raped, or even just not match the expectations we'd both now set so high.

The night was originally set for the end of the week, yet as the weekend continued we both knew we couldn't wait that long. Fate stepped in and gave us Monday. After a flurry of emails, we agreed to meet at my house.

The entire drive home from work that day was filled with so many conflicting emotions – excitement, lust, fear, terror, doubt. All the while one prevailing though trailed through my head –

What the hell am I doing?

Here I was a mother now, acting like a teenager and following my hormones. Having bragged about sex skills that I truly haven't used since college, could I possibly measure up to his expectations?

As I pulled into the parking lot I noticed the car in front of me. It's him. No more time to question, it's time to see how much of his bragging was the same as mine. We walked up to the house exchanging small talk. About what exactly I couldn't tell you. My heart was hammering so hard I could barely hear him, and the blood it was pumping so fast was going anywhere but my brain. We walked inside, shut the door, and then it happened – I came unglued.

As soon as the lock clicked, his hand was up my skirt. His fingers quickly found my clit and rubbed it fast and hard, his other fingers sliding inside me. As I hurtled toward my first orgasm I suddenly remembered my jacket. Odd thing to remember right then, but it was covered in a smoky smell I knew he couldn't have on him. Quickly, I tried to push him back, trying to form words with a brain that only had sex on its mind.

"Careful of the jacket. It's covered in smoke," I finally manage to squeak out.

He backed off the jacket, but his fingers never stopped, bringing me closer and closer to orgasm.

He asked me if that's what I wanted, if I wanted to cum. At least I think that's what he was saying – my brain was so scrambled by the onslaught of sensations words were not truly penetrating the haze. Suddenly he stopped everything and stepped back.

"Not yet" he says licking the taste of me off his fingers. "Take off the jacket"

I barely had my jacket hung up, and my purse set down when he's on me again. Pulling me closer this time, thrilling me with his kisses as his amazing fingers danced around my clit again. He starts asking me if I want his cock, if I want to suck it just as promised. I respond, "take me upstairs and I will" He continued to finger my clit expertly gliding over it ,swirling around it, causing my knees to go weak and all other senses to shut down.

I tried to get my leg higher. I want to give him more room, give him the edge he might need to throw me over, and admittedly find my balance. He's much taller than me, and finding a perch to set my leg and keeping my dripping wet pussy off his clothes is proving to be difficult. Faced with the onslaught of his fingers, it's proving impossible.

On the brink of another orgasm, he drops his hand and in a surprisingly calm voice says, "Take me upstairs." As he followed me upstairs, stopping to grope and grind several times, my thoughts betrayed the sensations coursing through my body.

I'm so far over my head here

is the most prevailing thought.

But sex is just like riding a bicycle – something you never forget. Right? I soon discovered that was the most naive thought I've ever had.

We reach the top of the stairs, and this time I try and turn the tables by jumping him before he has a chance to throw me off balance again. I stroke his rapidly hardening cock through his pants as my other hand undoes his belt. By now I'm shaking so bad from being so close to orgasm twice, and from blinding nervousness, that I can't undo his pants. He takes off his shirt and I take a moment to try and calm my nerves by running my hands over his chest. Hairy chests aren't usually my thing, but it works for me today. The bare skin contact calming my nerves, sparking my libido, and quieting my doubts enough that when I reach for his pants again I'm able to finally undo them. Finally able to get my hand around his rock-hard cock – the cock I've desired so much for the past few days. I lightly stroke him, testing him reactions, gauging his size, enjoying the quiet hisses he's making in reaction to my touch. Reactions he seems to be trying to hide from me, but he shows his desire when his hands move to my shoulders, slowly guiding me to my knees.

For the first time in years, I'm face to face with a hard cock. A cock expecting to find delight in my mouth. I remember a saying I once heard "Even when it's the worst oral sex you've ever received, it still feels so damn good." Figuring I had nothing to lose, I dart my tongue out to catch the pre-cum seeping out of him. For the first time in my life, my stomach doesn't retch at the taste. For the first time I find myself enjoying the taste, enjoying the salty/sweet mix that is him. I trail my tongue over him, trying to reach more of him, trying to prove to him, and admittedly me, that I can do this. That I can do this well.

His hands grabbed my head, forcing my head forward, pushing himself into my mouth. The doubts quickly rise to the forefront again – sucking's never been my talent. I discover that while I still don't excel at sucking, I can at least take a cock deep into my mouth without long buried demons haunting my brain. While my train of thought is an express to doubt central station, my mouth's on auto-pilot -sucking him, carefully watching out for my teeth as he shallowly fucks my mouth.

Attempting to put this embarrassment behind me, and move on to others, I rise to my feet and start kissing him again. Sliding my body against his, trying to use the skills I know I still have to distract him from the promised ones I don't. He reaches for my shirt, attempting to pop the buttons in his haste to pull it from my body. Quickly I back off, telling him to be careful – that I need to wear this same outfit to the sitter tonight.

"Giving me rules, not sure I like that," he grumbles in an amazingly sexy low gravelly voice.

"Fate gave some things today, but it sucks in other ways," I answer beginning to kiss him again as he undoes the buttons of my shirt, baring my breasts to his view.

His mouth dropped to them, licking and kissing the tops as his hands fumbled to undo he clasp. The wetness came flooding back, his kisses reminding my body it had been left on the brink twice with no release. Just as I was about to help him with the clasp (a part of me glad to see his was at least clumsy with one thing today) he finally got it. As I shrugged off the shirt and bra, he descended on my nipple – sucking it into his mouth for a brief second before releasing it. I undid my skirt, letting it slide to the floor, giving him his first look at the treat I'd worn just for him – stockings and garters. His eyes instantly glazed over with lust, and his fingers dove under the edge of my panties.

"They're over the top" I breathily managed to day. "They can come off." My body is aching for release, and I'm trying everything to get him to let me cum. He stops for a brief moment, only long enough to allow me to slide them off, before diving back in, finally allowing me release. My body explodes, causing my knees to weaken and my vision to blur, only then does he move me towards the bed.

He sits on the mattress, pulling me down with him, pulling me kneeling between his legs. I take him in my mouth again, trying to suck him like I've told him I could in my emails, trying to remember how to do this as his cock slides further into my mouth hitting my throat. I try to control my gag reflex, trying not to choke.

In a frustrated tone of voice he tells me "Get up here." He lies back as I crawl up his body. I kneel over him, bracing myself for the brief pain I always feel when first taking a cock into my pussy, but the pain never comes. For once in my life I'm able to slide straight down on a dick with no hint of pain, and a whole lot of pleasure.

I slide down as far as I can, relishing the feel of him, feeling myself relax, feeling how full he makes me feel, and truly thanking the gods that I did this with someone last week. See, on top has never been my favorite position; it always felt awkward and showed my lack of skills so glaringly I had avoided it like the plague until last week. Last week I'd put everything I'd learned from reading erotic stories to the test, and been rewarded with amazing orgasms. So, I proceeded to do what I knew worked – grinding my hips, circling them slowly, trying to drive him out of his mind. But he changed the rules.

He grabbed my hips and began moving me up and down - telling me to fuck him, to take it all, to ride him. The confidence I gained last week quickly evaporated, but I was determined to prove myself to him. I reached for the wall to balance with, and began bouncing on his cock, as his hands on my hips pulled me down harder each time, pulling more of himself into me.

"Can you take it all," I remember him asking with a challenging smirk before pulling me down hard onto him. Pain exploded deep inside my pussy as he thrust deeper than any man has, leaving me breathless with the pleasure of the pain.

"Put me on all fours and I can," I challenge him, but he wouldn't rise to the bait. He merely chuckled, and continued to aid my riding of him. Eventually telling me to suck it.

I slid back down his body, wanting to please him, but truly questioning what I'd gotten into at this point. I sucked him in, pitifully licking every inch of him, trying again to suck him deep.

"C'mon suck it," he said playing on my fears, confirming, at least in my mind, my inadequacies.

He called me back up to him, to ride his cock again. We repeated this time and time again, each time my legs hurting more, each time my breaths coming faster.

Finally he took pity on me and told me to get on my back. Curious to see his reaction to such a command, I balked. I lay there running my hands over his body, trying to see if I could distract him from his repeated requests to lie on my back. Finally, I got my answer about just how dominate he really was when he forcefully flipped me onto my back, sending strong waves of arousal coursing through my body.

He pulled my legs over my head, bending me in half, testing my flexibility, as he slid his cock into me. He started thrusting hard, filling me with delight at the sensations. I squeezed him harder, driving him on more, causing him to thrust harder, trying to draw him deeper.

Unfortunately, I draw him too deep and he hits bottom. Agonizing pain exploded through my body causing my vision to blur in its intensity. I push him back, pulling my legs down, telling him to do it with my legs lower.

Respectfully he stops, even though I know he wants to continue. "That's the spot I love," he cockily spits at me. "Why is it men with even bigger dicks than me can never find that spot?"

He slides off me, lying on his side next to me, his fingers deftly caressing me to orgasm again. Suddenly he stopped.

"I don't remember if I locked my car or not" he says.

I stare at him in disbelief. How can he possibly be thinking about his car right now? Doubt flares it's head again –

I'm so bad I'm not even holding his attention.

Then it dawns on me, he wants me to go check.

"It's a test," I say to him. "You're testing to see if I'll do it"

He reassures me it's not, but I'm steadfast in thinking there's no way in hell I'm going outside right now. Eventually he lets it drop, flipping back onto his back, pulling me astride him again. Teasing me about how dry I suddenly am (funny how pain and a side discussion about locked cars will do that to a woman). I try to slide him in hard and fast anyway – god knows I've fucked men while dry as a bone before, but he stops me. He eases me back down, slowly entering me, surprisingly gentle in the way he encourages the wetness to return – and return it does.

After fucking me hard, he asks me to suck it again. For the first time, I actually hear him groan. Apparently I'm getting the hang of it again.

"Do I have to get another woman in here to show you how to suck cock?"

Apparently, I'm not. His blunt blow to my ego causes me to redouble my efforts, shoving his cock down my throat, banging my tonsils so hard my throat's sore for hours afterwards.

"Get up here," he says again.

I climb up his body once more, sinking him inside me in one quick stroke. "Move and I'll cum," he says the tension of holding it back etched on his face. Pride finally swells in me...the power to put a man in this position one of my favorite parts of sex.

I squeeze very lightly, just enough to show him what I could do, and bringing the first true smile to his face that I've seen all day. "Should I reach into the drawer," I ask, cockiness returning to my voice.

"Yes," he grunts, his vigorous nodding communicating his need for the condom more than his words ever could have.

Once handed to him, he quickly puts it on, and pulls me back down to him. He sets a hard fast rhythm, telling me to squeeze him hard, "fuck me" becoming his constant litany as I brace myself on the wall, and try to match his demanding rhythm. He pulls me down hard, ramming deep inside me, and lets out the most satisfying groaning shout I think I've ever heard. I continue to squeeze him, trying to draw him higher. Finally, I collapse on top of him.

"Much better than advertised," I say causing him to chuckle.

"Do you have a bathroom up here?" his response.

As he cleans himself up, my emotions begin a rollercoaster ride. Embarrassment at the condition of the bathroom, nice floaty feeling from the orgasms, shame at my lack of skills, pride in giving him an orgasm, and a hundred others run through my head.

Just like the last guy I fucked, he wanted out so fast he practically left skid marks. At least when this guy ran out, he was gentlemanly enough to try and convince me it was nothing but a time issue, and was for no other reason.

Kissing me good-bye at the door, I finally ask the question, covering my insecurities once again with cocky attitude, hoping he'll at least lie to me. "So was I as advertised?"

He chuckled, adopted a cocky smirk, and said, "I just think you're out of your league."

Then he shut the door and was gone.

In real life, meeting a stranger from the internet was nothing like what you read in Penthouse. Along the way I discovered something, his post wasn't really meant for me after all. He wanted someone with experience, someone who was all the things my cocky attitude portrayed me to be.

Turns out, I still needed a coach if I wanted to play in my attitude's league.