Anna and Me

Disclaimer: For all intent and purposes, this disclaimer is here to note that these are real stories and events. The experiences are being recalled to the best of my knowledge of what actually happened.

*****

I met this Hispanic girl through a dating site. She approached me actually, and I thought for once I could get lucky. She was very forward, and invited me out for drinks sometime. I like it when a girl makes the first move when it comes to dating. If she likes to make the first move with a date, she may be a little more aggressive in the bedroom. We'll call her Anna. So, the night came when Anna and I went out to get some drinks.

We didn't spend much time at the bar. We just had a few drinks, and then went to get some fresh air. There was a park nearby, and we took a seat at a few benches. Mindless conversation was the main entertainment, but since it was dark out, there was a chance to get frisky and test some exhibitionism. I told her how I've learned to give massages from a friend of a friend who was a masseuse. It was my trump card in college, and usually worked. She took the bait, and since we were on a bench, she sat in my lap as I started on her shoulders.

"So, why on a dating site. Young girl in college, I'm sure you have a social life better than the internet."

"I do, but I recently got out of a bad relationship. I was looking for more, mainly when it came to sex."

"You're not looking for anything serious?" I moved my hands down her back. "No relationships?"

"Not at the moment. I just want to have some fun, ya know?"

"Is that why you contacted me?"

"Well, I liked what I saw on your profile. And after chatting for a bit, I thought why not."

"I'm not looking for anything serious either." I started to rub her lower back and around her waist. "So, if we're talking about sex, mind if I ask about your interests?"

"In sex? I'm pretty open-minded about it. How far have you gone?"

"I'm not a virgin if that's what you mean."

"No, like...what are some of your interests?"

"Oh, I'm into some pretty kinky stuff. I'm a fan of bondage."

"Like to be tied up?"

"I like an aggressive girl."

She laughed. "I can be pretty aggressive sometimes."

I started to move back up her back, and towards her collarbone. "What about...uhm, anal? I know not everyone is into it. Personally, I don't see the thrill of a guy fucking a girl. I don't see how they get pleasure from it."

"Oh they do. I've cum a few times from anal."

"Really? Have you ever given, or just received?"

"Received...What do you mean give anal? Like, with a toy?"

"A strap-on. Ever hear of pegging?" I rubbed just above her breasts. She nestled into me.

"No, what is it?"

"It's when a girl fucks a guy with a strap-on."

"Oh, I've never done that. It sounds hot though...have you ever done it?"

"I don't talk about it much, but since we're talking about it...yeah I'm a fan of getting pegged too."

"You like to get fucked in the ass?"

"Only by a girl."

"You're not gay or bi?"

"Nope. Boobs and pussy all the way." We had a little laugh.

"So...what is it about getting pegged you like?"

"Well, I like the idea of the girl taking control. And, I'm a bit proud of how much I can take."

"How much can you fit?"

"Right now? The most I've taken is 12" in my ass."

"Holy shit, really? That's a lot!"

"It is, but it feels so damn good...and if the girl really knows what she's doing, she can make me squirt."

"What, like a girl?"

"Yeah basically."

"Wow, I didn't even know guys could do that..."

"You know, if you want, I can show you sometime."

"Really? I might take you up on that."

The conversation went on for a bit longer before we went our separate ways. Since we went to the same college, I knew I'd see her around.

***********************

A few days later, Anna and I decided to meet up at the library to study together. The college library had those private study rooms for 2 or more people. We got one to ourselves and set up our laptops.

We were basically reading to ourselves, going over homework, but something kept bugging me. "Whatch'ya thinking about?"

"I keep thinking about pegging you."

"What?!"

"Ever since you've said it, I've been getting the urge like every day. I want to watch you take that 12". I'm thinking about it right now, actually."

"Fuck, then what are we doing here? Do you wanna come to my place?"

She smiled. "Sure. By the way, do you smoke? I brought some."

"Like, weed?"

"Yeah."

"Uhm... yeah!" Fuck, I scored with this girl. We packed up our stuff. I followed her to her place, and then gave her a ride to mine. I told her before I show her my tricks, I'd have to "prepare." So, I put on a movie, packed a few bowls of bud, and after I got a good high going and felt more relaxed, I went into my bathroom with my douche, stripped down, and got to cleaning up. I wanted to impress this chick. I didn't want to be flaccid and soft like I was with that blonde femdom. Getting high always gets me super hard. In case things got going and we fucked, I wanted Anna to know she was going to be mounting a big cock.

After I cleaned up, I walked out into my room naked. I could tell Anna was getting turned on. She smiled at me, and looked right at my dick. I got a duffle bag out of my closet and a towel. I put the towel on the bed, sifted through the duffle bag, pulled out a butt plug and some latex gloves. I handed her the gloves. "I thought you might like to help me warm up."

She was stunned. "I thought you were going to just show me."

I sat on the bed and stroked myself in front of her. "Yeah, but you've never done this before. Don't you wanna see what it's like? If not, that's fine. I'll do it myself." We sat there in silence for a bit while I continued to stroke.

"Okay, sure, I'll get you started." She put on the gloves.

"Great." I handed her the butt plug and laid back with my legs spread. I put a little lube on the plug and stroked it. "A little goes a long way. Just take your time."

Anna lined the plug with my ass and gently rubbed it. I breathed easy. I didn't want her to get too carried away. Forcing it all in at once would be a bad start. She pushed the tip against my anus, and popped it in. Then, she slowly pushed the plug in until it filled me up. I let out a pleasurable sigh and started to stroke myself again. "If you want, you can play with it a bit to help me get ready for my toy." She did as I said, and lightly pushed on the plug. She didn't grab it or twist it or tease me. Just little nudges here and there while I stroked myself.

I started to lightly moan, and I think it made Anna nervous. She stopped nudging the butt plug, so I took it out. "Alright, now let me get the dildo." I put the plug in the sink, and got my 12" out of the bag. I showed it to her.

"You can take all of that?"

"It takes some lube and time, but yeah I can." I put some lube on the toy and lathered it up nice. I then handed it to her. "Would you like to give me a hand?" Before she could answer, I bent over in front of her. I wanted her to use it on me, so I waited in that position to see what she would do or say. After a few moments passed me by, I felt the tip of the dildo press up against my ass. Anna wiggled it around, applied some pressure, and then it slid in. I let out a small moan, and she lightly pumped the dildo inside of me. She started to find a nice rhythm and went deeper. "Oh yeah, that's good." She went 6" in, and then it stopped.

"I thought you could take it all."

"I can. Just apply some more lube."

Anna squirted some more lube onto the dildo and around the rim of my asshole. She started to work it a bit more, and then slid the rest in. "Oh fuuuuuuuck." That's when the real fun started. She worked up a rhythm and kept pushing the dildo deeper into me, pulled it out, and then pushed it back in. I tried to keep my moans down, but it proved to be a challenge. Then she did something that really set me off. She got right behind the dildo and started using her pelvis to thrust it into me.

I was in ecstasy, completely filled up, as this cute olive-skinned girl practicing pegging me. She grabbed my hips and kept pushing the dildo in with her pelvis. She giggled and pressed her hips forward, pushing all 12" into me, and pressing her pelvis against my ass. I completely lost it.

I started to furiously jack myself off as she continued to thrust into me. She then took her hands again, and started to rub my taint as she pumped the dildo in and out of me. "Oh fuck, I don't know what you're doing but it feels so fucking good." I never felt that kind of sensation before. I was going to burst. "Can I cum?"

"What?"

"Oh fuck, can I cum?!"

She laughed. "Sure."

I came a huge load onto the towel. I started to catch my breath, and then, she said the sexiest thing I've ever heard a woman say. "Spit it out."

"What?"

"I want you to use your ass to spit it out." I used my anal muscles to push the dildo out, and when about 3-6" were out, she retrieved the rest from my ass. I let out another moan, and she laughed. "Nice job."

I cleaned everything out in the sink, and then we went to bed.

*****************

The next day, I drove Anna back to her place. "So, that was fun last night."

"Yeah, it was."

"I wish I did more with it though."

"What do you mean?"

"Well, I wanted to really work you over, ya know? Use the dildo faster, fuck you harder."

"If you wanted to do that, why did you let me cum?"

"What?"

"Last night, I asked for your permission to cum. If you wanted to do more, you could have said 'no,' and I'd stop jacking off."

"Oh, that's what you were doing? Sorry, I'm still new to this."

I laughed. "Next time."

"How about now?"

"What, like at your place?"

"Yeah, I wanna do it again. Did you bring your toys with you?"

"Uhm, no. I don't bring my toys with me to college."

"Oh, okay. Next time I come over then." I dropped Anna off, and then drove to campus. Damn, she really was into it. Now I wish I brought some toys with me, I wouldn't mind some pegging before class. I felt myself get hard. Fuck, now I'm horny.

I pulled into the student parking lot, unzipped my jeans, and jacked off. There was no way I was going to be able to pay attention with all of this on my mind. When I was ready to blow, I stepped out and came next to my car. I then zipped up, grabbed my backpack, and went to class.

**************

Anna started to act weird all of a sudden. Whenever she came over, she'd show interest in pegging me, but as soon as I was cleaned up, she'd lose interest, or she'd be "too tired." Soon, she started to get mad at me whenever I brought it up, although half the time, she was flirting with me with the idea. I got a little annoyed, so I stopped talking about it. This girl was rare to me though, so I wasn't going to let her just slip through my fingers. I needed to try something to get her horny for the idea.

One day, Anna asked if I wanted to hang out when she got out of work. We could smoke, maybe have a few drinks. She asked if she could stay the night, because her car was in the shop, and she needed a ride to get around. This was my chance to put the moves on her. Before I left to pick her up, I made my usual preparations. I inserted a butt plug to wear over there, and then got a great idea. I made some more preparations around my bed for later.

Then, I left for Anna's workplace, but when I got there, she texted me that her boss was making her stay late for closing up. "No problem, I'll just get a few drinks. Meet me at the same bar as last time." I walked over to an old Irish pub and ordered a drink. Sitting on the stool was a little uncomfortable with my plug, especially with how big it was, but I managed to find a tolerable position. I simply surfed the web on my phone while I waited.

About an hour and several drinks later, Anna popped up. "Hey, sorry about that. It took forever. Do you wanna go?"

I smiled at her. "Sure, but first, I want to show you something." I grabbed her hand and placed it on my ass, right on the plug.

Her face lit up. "Is that—Oh my God, you've been wearing that the whole time?!" I nodded. She took out her purse. "Let me pay for your drinks." After she paid, we left and got into my car. "So, how long have you been wearing that?"

"About two hours."

"Damn, are you alright? Are you uncomfortable?"

"I was at first, but I'm fine now."

Anna laughed. "I'm gonna dom you so hard, you're not even gonna know what's happening." She laughed again. "Tonight's gonna be fun." Mission Accomplished.

We smoked a joint on the way to my house, and then another bowl after we arrived. I started to strip. "Do you want me to keep the plug in?"

"Do whatever you want."

"I'll make sure it's clean. But first," I grabbed my duffel bag of toys again. "I want you to wear this, this time." I pulled out a purple dildo attached to a harness. "Put it on, and I'll be right back." I went into the bathroom. I still had my douche loaded, so I used a couple of squirts. All clean. I came back out, and Anna was loading up my bong. She had the harness strapped around her waist and hips. A 7", erect, purple dildo was protruding from her pelvis. A lubricated condom was on it to ease it into me. I already started to get hot.

"Mind if I smoke some more?"

"Sure, no problem." She's gonna flip when she sees me. As Anna started to pack the bong, I put a towel on my bed, and then dug under it for the preparations I made earlier. I pulled out bondage cuffs tied to a strap from both sides. I locked my feet in, then crawled to my bedside drawer. I pulled out rope cuffs, a mask, and a gag. I put the gag in, and tied it just tight enough to stay in, but allowed room to talk. I then put on the mask, and the cuffs, and wrapped the cuffs so that my wrists were tightly bound. I got on my hands and knees, and stuck my ass out, ready and willing.

I could hear Anna smoke from the bong. She exhaled, and turned around. "Oh my God!" There was a pause, and then I heard her climb onto the bed. "You really prepared for this."

I mumbled, "Mhmhmm."

She giggled. "Good, because tonight's gonna get a little crazy." She moved forward and got on her knees. I felt her press the tip of the dildo against my waiting hole. I let out a long breath, and all at once, Anna thrust into me. I gasped. I didn't expect her to be so forceful. She immediately went to work and started to peg me with the strap-on. I was completely helpless to do anything but moan. I heard her laugh and make dirty comments to me.

Every so often, Anna would grab and massage my ass as she fucked me. "You like that, don't you?"

"Ohh yeaaah."

Anna stopped, and just held my ass there. The dildo was barely inside me. She then pulled me closer, and listened to me moan as another inch or two went in. She stopped again. "Work for it." I was happy to. I started to bounce my ass up and down, and backed up into the dildo. I could tell she refused to do any of the work. She didn't move at all, and left it up to me to please myself on the strap-on. She smacked my ass a few times, and then stopped me once more.

She pulled out, and left me wanting more. "Where's your 12"? Is it in the bag?"

"Yeah..."

"Okay, good." She went into my bag and retrieved the 12".

"If you're gonna use that, you need lube, remember."

"Oh yeah, okay." She grabbed some lube too. She took off the harness, and then got back on the bed behind me. She put on some lube on my ass and the dildo, and lined it up with my ass. I expected her to take her time with this one, but I was wrong. As soon as she got the head in, she jammed all 12" inside of me. I cried out, but it was short-lived as she furiously pounded the dildo into me. My hips buckled and my ass spasmed. I moaned with every thrust, and she didn't stop.

Anna started to massage my taint as she worked the dildo in and out of me. It felt so damn good, I couldn't help but surrender to her. After a couple of more thrusts, she did something I didn't expect. She searched for my dick and balls, and once she got a hold of my shaft, she started to jack me off. The pleasure was so intense, I must have been speaking complete gibberish, because after a couple of strokes, she stopped and put all of her focus on my ass. Anna continued to thrust into me as fast as she could.

The pleasure was building, I was sure I was going to squirt any second. I could feel her milking my prostate, the sensation of cumming kept coursing through my dick, but nothing came of it. Just drops of precum dripped onto the towel. "Want mercy?"

"What?" I gasped in between moans.

She pounded me harder. "Want mercy?"

I couldn't take it anymore. I thought maybe she was going to finally make me to cum, so I said it. "Mercy."

"Beg for it."

"Mercy." Anna just started to pound me as hard and as fast as she could. "Mercy, MERCY MERCY!!" My moans were so high-pitched I must have sounded like a girl about to orgasm. Anna laughed and pounded me a few more times before stopping. She pulled the 12" out of my ass, and let me lay there as I caught my breath. I heard her unstrap my feet.

"Turn over." I did as I was told. I was in no position to fight her now. Anna sat on top of my legs, and played with the dildo. She brushed it across my dick and stomach, teasing me with it. After a few moments of that, she sat up, lifted my legs, and reinserted the dildo. Once all 12" were in again, Anna got on top of me. She straddled me, and began to grind against my dick. Every so often, she would lean forward, grind her hips against me, and breathe on my lips. She'd then retract and start to grind me harder.

After teasing me like that, she straddled me. "So, what would you like to do now?" I pushed my hips forward and mumbled. "What was that?" I pushed my hips forward again, and bucked her until her hips bounced off my pelvis. "Oh you want to fuck." I mumbled again. "No, I don't think we're going to do that." I groaned. "Didn't you say you can squirt?" I mumbled a third time, and then she removed the gag from my mouth. "How do I go about making you squirt?"

I exhaled slowly. "You see the bondage gear I have? Take all four cuffs, the strap, and hog tie me. Then, just go to town on me like you were doing before. I'll squirt for sure." I could see her smile grow wide in the moonlight. She had this carnal look like she was going to own me there and now. I heard her rustling through my drawer; up went my legs, and soon my hands. She tied my wrists and ankles together tightly, all with the 12" still inside my ass.

"Like this?"

"Yeah, like that."

"Okay, good." She grabbed the 12". "Ready?"

"Yeah, I am."

"Do you squirt a lot?"

"Sometimes."

"Alright, let's see what we can do." She pulled some of the dildo out, and then started to pound me with it again. I threw my head back and moaned loudly. As she continued to thrust, my back would arch and my hips would rock with each one. The pleasure was filling me up so quickly, I thought I would cum all over my bed. My body shook, and a warmth spread through my ass and into my dick.

The pleasure was so great, I couldn't control my limbs. My legs shot up, practically over my head, and my ass spasmed. Anna continued to pound me, even harder now. She was relentless. My legs came back down, and I shook as she continued to work me over. I moaned several times, and then I felt it. Fluid rushed through my shaft and burst forth. It went on my stomach, my chest, and then the reserve dribbled onto my balls and down towards my ass.

I collapsed onto the bed. Anna let out a long breath, and finally retrieved the 12". I moaned as she left my ass empty. She put the dildo in the bathroom sink, washed her hands, and then sat next to me on the bed. She looked at me with a smile, grabbed my bong, and took another puff. "Now that was fun."