tagAnalEasy First Date

Easy First Date

byilsop©

My last boyfriend broke up with me because I was "too aggressive." Our society expects women to be passive during sex. I have never wanted to be a woman who just lies there, passive and moaning, spread-legged like a frog on a dinner plate. I love to be on top. I always straddled him and put my hands on his forearms so I could pin him down, and then I pounded my pussy into his crotch. When he got close, I'd slow down and go up and down in long, teasing strokes to finish him off. I loved to watch his face as he came. Once, he even moaned a little, and I was over the moon. Sadly, he broke up with me soon after.

In my post-break up horniness, I browsed the Internet for porn. I searched for "women in charge," and I soon was looking at bondage and dominatrix sites. This isn't what I like. Who would want to cause her lover pain? I want to cause him pleasure. There is an amazing power in that, gently forcing him to rapturous pleasure, gently making his body respond to my commands. There is plenty of porn where the man does this to his lover. I just wanted to see a normal, loving relationship... where it was the woman who did her man.

I was just about to give up when I saw my first pegging video. Pegging is when a woman wears a strap-on and anally penetrates a man. I had never heard of this before, and I was mesmerized. In the video I saw that first night, a brunette was naked except for a bright blue dildo. He was on the couch, doggy-style, and she was behind him. She clearly enjoyed stroking into him. He was clearly enjoyed himself, too, but he wasn't touching his penis. Then they switched positions. He lay down on his back, spread his legs, and brought his knees nearly up to his chest. She slid in, and you could clearly hear the slurp, slurp, slurp of a cock penetrating a wet orifice. She increased her speed until she was just slamming into him, and you could hear the slap of her crotch up against his ass. And then the most delightful sound: it started off soft but grew in volume, a plaintive moan of deep pleasure, very submissive but unmistakably baritone. "You like that, don't you?" she said, possessively. She thrust more rapidly, he moaned louder, and I started masturbating like a woman in heat. Without ever touching his penis, he came thickly onto his own chest, and the sight of it made me come.

How had I never known about this before? It clicked for me in a way that no other sexual act, real or fantasized, ever had. I knew that I must experience this. I made up for lost time. Over the following weeks, I did all the reading I could. I joined online groups, solicited advice, ordered equipment, and continued to masturbate to my new fantasy. I chose a Share silicon double dildo, so that I would be directly stimulated. The Share came in a light rose color that was roughly my skin tone. As much as possible, I wanted this dildo to look like "my" cock. On the advice of people on the message boards, I knew that although the double dildo would give me a lot of pleasure, it needed more support, especially during vigorous thrusting, so I also ordered a harness.

In the meantime, I imagined what having a cock might look like. Just for curiosity, I rolled up a sock and stuffed it into my panties. Looking in the mirror was surreal. Is a man's package really that big? In truth, the sock made for a pretty modest endowment, but I was shocked at how far it distending my figure. Let me be clear: I don't want to be a man. I like being a woman. I like clothes, shopping, and shoes. In almost all aspects of my life, I may even be girly. So why is it incongruous for a feminine woman to want to spread her man's legs, grab his hips, thrust into him, and hear him moan in pleasure? Is it only because a woman isn't born with the right equipment? Biology shouldn't be our destiny. I didn't want to be someone else's sex object anymore. Looking at myself in the mirror, the bulge in my underwear made this desire clear.

A few days later, the Share arrived. I scarcely drew a full breath as I opened the box. There it was: pink, almost my flesh tone; a shorter "pony" bulb for me; and long, firm cock for some new beau's butt. I put the shaft through the cock ring of the harness, slid the harness up my legs, closed my eyes, and spent a minute slowly penetrating myself with the bulb. I was already wet. Once it was in, I adjusted my harness until it was snug, stepped in front of the mirror, and opened my eyes. I nearly fainted. Given the similar skin tones, it almost looked like a real penis coming out of the harness. A woman looks in the mirror every day and sees a smooth, curvaceous body. Now there was a pointy, meaty finger poking jauntily out of my crotch. It looked so powerful, lust embodied. I touched it. Just a tentative tap at first, but even with that light touch, I felt some vibrations. I tried stroking it several different ways until I found that a firm grip and a lot of in and out transmitted vibrations right to my clit. Watching in the mirror, it really looked like the technique a man uses to jack off. I came. Hard.

I jacked off with the dildo every night for a week. What turned me on the most was a mental picture of a man's face in the moment that I penetrate him. Even when I had been on top, even when I had pinned him down, I wasn't really fucking him. It was still my body that was entered. My antics were really a distraction, an attempt to forget that he was inside my body, that I was the one being fucked. Now I can have what I have always wanted: to be the fucker. I want to know that he is completely vulnerable to me, opening up his body to me. I want to make him moan at every one of my loving thrusts, rapturous gratitude on his face.

The next week, I decided to go out looking for my new beau. I planned every detail. I might normally go out with my girlfriends, but they would slow me down tonight. Likewise, I needed to find a man who was alone; if he were with friends, then my attempt to pick him up would probably seem desperate. But I didn't want someone who was out on his own trying to pick up women, either - some douche-bag flying solo, looking to score. I needed to find a regular guy, just hanging out by himself. An airport bar might have done nicely, if there were a way to seal the deal, so I settled on a pool hall. Guys go there to relax, not to meet women. How many single women have you ever met at a pool hall?

I dressed casually: jeans and a nice blouse. No reason to attract too much undue attention. When I got to the pool hall, I ordered myself a bourbon sour and sat at the bar. As I sipped my drink, I looked over the pickings: two frat boys playing at the back table, the coed threesome on the left table, an old man at the bar watching the baseball game on TV, and a well-muscled man chatting up the hot bartender. I might have just finished my drink and left, but a good-looking guy walked in and asked for a table. He had sandy blond air, a lean and trim body, and a cute face, but I wanted to watch him for a few minutes to see if he was alone. I ordered another drink and tried to act like I was into baseball while I peeked at him. Ten minutes later, he was still alone. I decided to make my move. I needed to play it cool. No guy is going to say no to sex, but guys are skittish that any girl hitting on them is emotionally needy and acts as if she's looking for a serious boyfriend. There was a real risk of striking out. I strolled up to him and casually said:

"Are you playing alone?"

He looked up at me, and then flashed a quick smile. He had brown hair and soft green eyes, and there was something gentle about his face. "Yeah, I guess. I was meeting a friend here, but he just called to say he was bailing. Traffic." He paused.

"Well, I'd like to play you, if you wouldn't mind."

Another smile. "Baseball not doing it for you?"

"No, not really my game. Well, shall we?" I asked. "I'm Megan."

"Steve." He racked the balls. As we played, I found out a little about him. Steve was a graduate student in computer science. "Theoretical work only; nothing practical about it at all," he joked. He was a year younger than me, and he had also recently ended a serious relationship. "I chose this graduate program to stay with her, but it just wasn't working out." He was kind and gentle - maybe a little too passive for a man. And he had been the opposite of a flirt.

I asked him, "Why would your girlfriend leave someone as nice as you? You're such a sweetheart." It was risky. I might have scared him off with that prying question - looking like a would-be high-maintenance girlfriend - but he responded. She had wanted someone tougher. Now I was certain: I knew he would let me drill his ass. I was ready to test that. Tonight. I sank the eight ball, and another game was over. It was nice to go out on at least one win. "Well, I guess I should be going," I said facetiously.

"Umm, yeah." He looked at his watch. It wasn't really late. "Well, I might stay a few. My bus leaves in 25 minutes."

Excellent, luck was on my side! "I can give you a lift home now, if you like." He looked at me, sizing up the situation. I waited for the longest five seconds of my life, my heart in my throat. Then he said, "Yeah, that'd be great." A wave of relief washed over me, and in retrospect, I was being silly. What man would turn down a ride from a beautiful woman? We got in my car, and I drove to his place. I pulled up along the curb and parked.

"Well, thanks for the ride," he said.

"You're welcome," and then I leaned over and kissed him. It was a long kiss. I found myself imaging his ass cheeks spread wide open for me, and I realized I had my hand behind his head, pulling him in hard for the kiss. He wasn't resisting, though. I broke the kiss.

He sucked in his breath. "Megan, I like you, but I just had a bad break-up, and I'm not sure I'm ready for another relationship yet."

"I'm not looking for a relationship, Steve. I want to have sex tonight, with you. No strings attached." I paused. He seemed shocked. "Think of me as a rebound screw."

After a moment, he said, "That sounds nice." I gave him a quick kiss, and we got out of the car. I grabbed my purse with my harness and strap-on, and we went inside.

* * *

My girlfriend had just broken up with me, saying I was a pussy in bed. I always tried to take care of her needs, and her remarks cut. My friend Doug said we should shoot some pool and drown my woes. Of course, he was a shit and got stuck in traffic. That's how I met Megan.

Her black hair was cut short, almost a boy's style. She had nice B-cup breasts and a great body. She was sitting alone watching baseball, so I figured that she was a lesbian. I was surprised when she came up to talk and flirt with me, shocked when she offered me a ride home, and floored when she said she wanted to have sex. I didn't know what to think. Was she really looking for a boyfriend? Then I realized, Who cares? I was lonely, and being with someone tonight would be comforting.

As soon as we were in the door of my apartment, she was kissing me. I'm a soft and slow kisser, but she was aggressive. I didn't mind. In another minute, she was pushing me down onto the couch. Before I knew it, she had my shirt off and was licking my nipples. No girl had done that to me before. It was surprisingly pleasurable. "Oh," I gasped.

She smiled at me. "Feels good, doesn't it, baby?"

"I never knew it did."

"I think you'll make a lot of discoveries like that tonight," she said. "Let's get these pants off of you," she purred. I kicked off my shoes and got my butt up off the couch, and she pulled my pants and underwear down in one swift motion. She kneeled between my legs and started sucking my hard cock. She licked up one side of my shaft and down the other. She swirled her tongue around the tip before taking a mouthful. Her hand clamped on my shaft and pumped back and forth. Her tongue moved to my balls, and she gave some playful licks. Soon, her tongue was behind my balls, roaming up and down my taint. Before I knew it, she was licking my asshole.

"Whoa, Megan, I - "

"Relax, baby," she said, pausing. "Do you like it?"

"I mean, yeah, but..." but before I could complete my thought, she was slurping at my back door again with gusto, pumping my cock with her fist. I had never been rimmed before. Damn, it felt good. She alternated between long licks from ass to balls and back again and a gentle, insistent probing of my asshole. I was more sensitive down there than I had realized.

"Slide forward," she told me. I slid down the couch. "Are you enjoying?" I responded with a sigh of pleasure. She rewarded me with reinvigorated rimming. I closed my eyes and drank in the wonderful sensations. Damn, this girl was a slut! Two minutes later, she was sucking my cock again. Her hand moved to rubbing my taint. It was sopping wet and slippery. Her fingers were running up and down my crack. And then her middle finger stopped, right on my asshole, and she started to push. I was startled from my reverie.

"Megan, what are you doing?"

"I want to finger you, Steve."

"What?!"

"I want to put my finger up your asshole," she said as she stared at me lustfully. "Trust me. It's going to feel great." Before I could answer, she pushed her finger in. "See how relaxed you are?" Then she pushed her finger in past the second knuckle.

"Oh my!"

She leered at me. She went back to sucking my cock, timing her sucking to match the stroking inside me with her finger. At first, I was scared stiff. But it felt fantastic, like nothing I'd experienced. I lost myself in the pleasure.

"Here, move your legs up. Give me more access," she said, pushing my knee back into the couch. I complied and lifted my feet off the floor. I tried to rest my feet on the couch, but she grunted, "No, farther," and I moved my knees until they were nearly even with my chest. My feet were dangling in the air. She got up off her knees to kiss me. She was pressing her body down into mine. I could feel her weight pushing down on me, light though she was. I ran my hands through her short, dark hair. Her hand snaked up my thigh, and I grunted in anticipation. She stuck two fingers in me and thrust them in and out. She wasn't even touching my dick, but the sensations were amazing. I felt like I might come eventually just from the fingering. Then she stopped. I opened my eyes, to see her staring at me with a wicked smile on her face, fingers still in me.

"I want to fuck you, Steve."

"God damn, I want to fuck you, too. Let's get in bed."

"No," she said, shaking her head. "I want to fuck you." As she spoke, she wiggled her fingers for emphasis. "I want to put on my strap-on dildo, and fuck you up your ass." She let the words just hang there. They snapped me awake from the dizzying sexual feelings instantly. Instantly, everything had flipped 180 degrees. I realized I was lying down, legs spread and feet up in the air, with fingers up my ass. She wasn't a slut. I realized she had intended this all along to work me towards this moment. I was to be the slut. I felt vulnerable and exposed and shocked, and her lascivious face was too close to mine.

"I can't," I said lamely.

"Yes, you can. You already are. Or doesn't this feel good?" She waggled her fingers again.

"I guess, yeah."

"You'll have the best orgasm you've ever had." Based on what I'd already felt, that might well be true.

"I don't know..."

"Trust me, please." Her expression had softened. I relaxed a little. This wasn't some getting-even-with-all-men thing. I mean, this was still fucking bizarre, and I had only known her for a few hours, but for some reason I did trust her. I felt my resolve melt a little. Somewhere, in the far back of my mind, I heard my ex-girlfriend saying that I wasn't much of a man, anyway. I thought, Fuck you, maybe someone likes me just how I am.

"Alright," I said softly.

She broke out in a huge grin. "You won't regret it, baby. I'm going to make you cum so hard. I'll be right back." She grabbed her purse and skipped down the hallway to the bathroom. The light flickered on, and the door closed. I sat up on the couch, smearing my wet bottom all over the leather. It felt so strange. What the hell was I about to do? I was more nervous than I'd ever been before sex. Even my first time, I was nervous, but not like this. I heard the bathroom door close, and I looked up. She stood at the door to the room, almost totally naked. I saw her beautiful breasts for the first time. My eyes hesitantly roamed lower. The harness looked like leather panties. There, like a lighthouse on an island, was her dildo. It looked like a real dick. I was terrified but I couldn't look away.

"Megan, you're beautiful."

"You're pretty damn hot, too." She walked over and sat next to me. The dildo pointed up out of her crotch. I stared at it. Up close, I could tell it was a dildo, although it had a realistic shape. It looked huge. "Do you like it?" she asked, giving it a playful stroke.

"Can you feel anything?"

"Not directly, no. But there's a second dildo inside that rubs me just fine when I move. Speaking of moves..." She leaned over and kissed me deeply. I realized that I didn't need to take any initiative tonight. Her hand was pinching my nipple. Soon, she was pushing me over, and I put my head on the armrest. "Baby, this is only going to work if you spread your legs." I complied, and she nestled tighter on top of me. Her hand was instantly at my asshole, fingering me again. I moaned in surprise. "Yeah, that's it. Show me how much you enjoy it." She reached down to her purse for lube and started to lube up her dildo.

Oh, what was I about to do? "Put your legs up." I lifted them again. I felt the head of the dildo at my back door. "Relax, baby. This will only sting for a second." And with that, she gave a good push, and it popped in. It did hurt, and I winced. "Relax. Breathe. Just let your body get used to it." I tried to think about anything besides the fact that a dildo was going up my ass. In a few moments, it did stop smarting. All that was left was a pleasant feeling of fullness. "Are you ready for more?" I nodded, and she slid more in. It felt like I couldn't possible take any more, but it kept going. Then I felt her crotch grind against my butt.

"That's it. You've taken the whole thing." I felt a little proud, and I smiled. "Now," she said, "I'm going to pound your ass. I'm going to fuck you senseless." With that, she gave a big, slow thrust. I gasped.

"Feels good, doesn't it?"

"Oh, fuck, I had no idea," I said breathlessly. She kept up a steady rhythm. Each stroke sparked a shower of sensations in my body.

"Wrap your legs around my back." I did. "Does that feel any different?"

"Not really."

"How about this?" She changed her angle.

"Oh my god." It made my eyes roll back; it felt so good.

"Oh yeah?" She picked up the pace. Her strokes were faster and harder. I was delirious. I was moaning. I started bucking my hips up to match her thrusts. I wanted to feel the dildo as deeply as possible. I could feel her dildo deep inside me, opening me up. I put my hands on her butt.

"Fuck, fuck. Megan. Fuck me. Oh, fuck me harder, Megan." She speeded up, pounding away at me. I was so close. I arched my back and pulled her even deeper into me with my legs. She slowed down, teasing me, until one long, perfectly timed slow stroke pushed me over the edge. "Oh, damn, I'm coming." I felt my asshole contract on her dildo, and I spurted all over my chest. I nearly blacked out. It was the best orgasm of my life. Thirty seconds later, I was still coming down. My legs were trembling. "Oh, damn, I'm sorry," I said.

"For what?"

"For coming so quickly. You didn't come yet, did you?"

"No," she said, and then she smiled. "We're not done yet. On your hands and knees." I could get used to this.

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by Anonymous

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by horny4itnow05/01/14

Easy first date

Wow meet a gal like this that makes a guy her bitch. just made me cum oh my

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by Anonymous12/23/13

Where can I can meet you?

How cum I haven't run into a hottie like you spotting a strap on? Top 3 fantasy of mine;)

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by Anonymous12/01/13

I hope we get more of this story....

Very interesting story line. From both partners view; at least a bit. I'm hoping for 'The Rest of the Story' - the next date (s)!!!
Very well done. Makes me wish my lovely lady would do it to me....whomore...

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It takes a man . . .

Young men rarely consider this kind of play but maturity and confidence permit a mature man to relax and enjoy. Not always, of course, but historically that's been the case. I'm hoping the current generationmore...

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by Anonymous08/31/13

Thank you for this beautiful fantasy.

Megan is forceful but not brutal, assertive but not tyrannical... the perfect partner. Again, thank you.

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