The way to my boyfriend's heart was through his ass!
I met Brent at Barnes & Noble, actually. He was working, and I was looking for a particular book of poetry. He was very sweet and helped me find it, walking me all the way to the shelf to make sure I had it in my hands. It seemed rather unnecessary, but I admired his earnestness. He was also really cute.
I came back a few days later in hopes of seeing him. This time I had to make up a book for him to find, so we could spend countless minutes together looking for it. I got rather nervous when he found a book of the same title, thinking I’d have to buy it if he produced it, but fortunately even that one was out of stock. Of course it didn’t matter, and shortly thereafter he managed to ask for my number. I played coy for a few seconds before giving it to him, feeling like such a girl playing such games. I flirted like crazy before I left, making sure he’d call sooner than later.
Sure enough, Brent called the next day. We made plans and got together that weekend, typical dinner and movie fare, but it was fun. He was funny and sweet, and I had him eating out of my hand. Don’t get me wrong; I’m not a power-trip kind of gal, but you’ve gotta admit it’s fun to watch boys bow and scrape on occasion. Anyway, I was crushing on him just as bad, and we seemed like a perfect fit from the beginning.
That was a few months ago. We’ve spent lots of time together since, and sex was steadily creeping into the purview of the conversation. I don’t think I’m terribly easy, but I love getting laid, and I had it in for Brent. I just didn’t want HIM to know that too quickly.
We made out tons. Lots of groping, fondling, kissing, even some licking. Brent loves my titties, which is great because I love to have him suck on them. In truth, I was begging him in my mind to just stick his big pecker inside me. I think he knew, but he never got too direct. Thank God, because I don’t know if I would had the self-control to stop him.
Finally the day came when I was ready to have him. I invited him over, kicked out my roommate, and made dinner. We ate, made out on the couch like usual, and ended up on my bed in some hot dry-humping. Well, it wasn’t very dry, because my pussy was soaking wet. I stopped him and told him to strip. He looked at me in disbelief, then jumped off the bed and stripped naked in mere seconds. I had to laugh at his enthusiasm. But I wasn’t laughing at his cock, which was lovely and rather large. It was probably over seven inches; a little scary but totally delicious. I pulled Brent onto the bed and rolled on top of him. I put his cock in my mouth and sucked him hard. He moaned and gasped and soon he was thrusting up into my mouth. I pumped his cock hard with my fist. It wasn’t two minutes before he came. I could actually hear his cum erupting from his hard cock. I wasn’t really ready, and I kept sucking him off, but I let most of his cum leak out and run down the length of his pecker. It was glistening and creamy beneath my hand, and he whimpered softly while I sucked his cum out of him.
I got up and grabbed a towel to clean him off. While I cleaned him, he asked me to strip. When I finished wiping up, I pulled off my t-shirt and detached my bra. My little titties popped out, and Brent smiled. I toyed with him nipples seductively, hoping he’d be ready for more action before too long. He played with his soft dick while I touched myself. It was really hot to watch him touch himself. My pussy was already drenched, but now my clit was buzzing like an alarm clock in my head. I pulled off my shorts. Brent watched as I slipped a hand under my panties. He watched in fascination as I touched myself behind the white cotton barrier. His cock appeared to be hardening before my eyes, and his stroking became more diligent.
I couldn’t stand it anymore. I pulled my wet fingers out and slid my panties off. Brent’s eyes went wide. I could tell he admired my neat trim job. I felt very sexy standing there, and started to finger myself again. We continued like this for several minutes, Brent on the bed pulling on his stiffening cock, me standing at the foot of the bed rubbing at my aching clit.
His cock was now completely hard, and if I rubbed my pussy anymore I was going to come. I stepped over to the dresser and retrieved a pre-stashed condom from the top. I sat on the bed and put it on him. He let me put it on him without interference, though I almost asked for his help at a few places.
Finally we got the condom on, and I straddled him quickly. I slipped him inside, and we both gasped. It felt fantastic. I rode him slowly, just enjoying the feel of him inside me. But Brent was reaching into places I’d never felt before. His cock felt huge, but it never hurt. I sped up, riding him hard, sliding my sopping wet pussy up and down on his shaft. He manhandled my titties, which felt great. I fucked him harder, and soon I was cumming. I slammed myself down hard and ground my clit against him. He bucked hard and came almost immediately. We came almost together. It was amazing.
After sex, we cuddled and talked and kissed for hours. We even took a shower together, and then returned to the bed. Later Brent went down on me, and ate my pussy until I came hard. I fucked his face while he licked my pussy and sucked my clit. He’s great at it, and he loves doing it whenever I want. After I came, told him I wanted to blow him again. He didn’t argue, and I got between his legs and started to lick and suck his cock again. I felt it harden in my mouth, which is an amazing sensation that I have loved repeating many times since.
As I sucked on him, Brent’s hands came down and fondled his balls. I took the hint and started to play with his nuts. He moaned loudly, so I continued. I’m a good sport, so I tried licking and sucking them. Brent loved that, gasping and encouraging me. I sucked his balls while I jerked his cock, then I went back to sucking his cock. I kept playing with his balls. As I massaged them, my fingertip grazed his asshole. Brent bucked wildly, thrusting his cock deep into my mouth and groaning very loudly. I was surprised, thinking I’d hurt him or something. I was also curious, so a few seconds later I grazed his butthole again. He bucked again. I was having so much fun turning him on that I decided to try something crazy.
I went back to sucking his balls, and took a chance. I darted my tongue at his asshole. I knew it was clean because we’d just showered not long before. Brent went crazy. I went for it. I started licking at his asshole, all the while pumping his cock with him hand and gently squeezing his balls with the other.
Brent was positively high, writhing in pure arousal as I tongued his hole. He spread his legs wider, eventually holding them out so that I had unfettered access to his ass. I was very thankful it was clean, but I was having a great time exploring my boyfriend’s secret spot. Finally as I pushed my index finger into his wetted anus, sucked his balls into my mouth and pumped his cock I felt and heard him cum. I dropped his balls from my lips and looked up. I kept jerking my hand and watched the spray of his cum arc across his stomach and chest. I pushed my finger all the way in, and he grunted. A final spurt of cum retched from the tip of his cock. Brent let his legs down. I sat there in amazement, my left hand covered in cum, my right hand’s index finger locked tight inside Brent’s asshole.
That was the beginning of “ass play” in our relationship. It turns out Brent is highly aroused by anal stimulation. It’s not really my thing as far as my own ass goes, but I was really turned on by the thought of playing with my man’s asshole. Soon fingering his butt during blowjobs was a frequent, though not regular, part of our lovemaking. Sometimes he’d want me to just lick it, and he’d masturbate while I tongued him. I tried to push my tongue in sometimes, but I guess my tongue’s not that strong. But I’d lick his butt and nibble his balls and he’d pound his peter and cum on himself. Other times Brent would have me insert a finger or even a thumb and tickle his prostate. I loved jabbing him with a digit while I blew him; he seemed to cum extra hard on those occasions.
I started fantasizing about fucking him in the ass with a dildo. I found that I was fascinated both by the idea of penetrating him deeply and the idea of having a cock of my own to wield to his satisfaction. I didn’t ask Brent if he was interested. Instead I talked with a lesbian friend of mine. I was a little embarrassed to ask, but Pam is so easy to talk to and she coaxed it out of me. I asked her about using strap-ons and things. She told me all about it, at least as far as she knew. She told me that when women fuck guys in the ass with dildos, it’s called ‘pegging’. She said that many lesbians who use them often strap them to their thighs because they’re easier to control that way. I didn’t really understand, but she had lots of other advice, including where to get one. She told me how much they cost and I almost flipped. I nearly asked if I could just borrow hers, but then I remembered where it was going to end up, and caught myself.
One Friday evening I went to the sex shop Pam had recommended. They had quite a selection of toys. There was a gay man working who seemed quite knowledgeable, and I felt comfortable telling him of my plan. He had some recommendations for the male ass, which made sense. I looked at some long, thin vibrators designed for the ass. I also looked at some big monster ones that got me feeling quite randy. I finally settled on a handheld butt vibrator and a full strap-on unit with interchangeable dildos. I selected a couple that I thought Brent could handle, plus some lube. It wasn’t cheap, but I thought taking my man’s ass play to a new level was worth it.
That night I schemed about how to seduce Brent into letting me fuck his ass. I realized I was as turned on by this thought as I hoped he would be. I ended up using both dildos and the vibrator on myself that night, even trying the vibrator in my ass to see what I was missing out on. It did feel amazing, and I had the butt vibrator buzzing in my pooper while I fucked myself with one of the dildos. I came quickly and fiercely. I cleaned up the toys and finished my plan.
Saturday I invited Brent to come over for dinner. I sent my roommate out once more for the night (poor girl). I made dinner again, and opened a nice bottle of wine. Brent arrived right on time. We enjoyed our meal, and relaxed on the couch with the wine. We kissed and cuddled, and I rubbed myself against his cock. I felt it harden through his jeans. I plied him with more wine, and we were soon feeling rather horny and amorous.
I led Brent to my bedroom. I stripped him seductively, and stripped myself. He sucked my titties and fondled my pussy. It was on fire in his hand, and I almost came from his fingering. I tugged his cock, which was hard as rock in my hand. I lay down on the bed and asked him to eat me. Brent knelt dutifully and tongue-fucked me to an amazing orgasm. I think I was so fired up over my plan that I was ready to explode, and I did when I came against Brent’s face. I fucked his mouth and screamed as my orgasm washed over me. Brent didn’t miss a beat and sucked my clit hard and I came a second time in a matter of seconds. Finally he stopped. I don’t think I’ve ever been so horny as I was at that moment. All I wanted was to enact my plan. I sat up and kissed him lovingly, tasting my pussy on his mouth.
I told Brent it was his turn. We switched places, him on his back on the bed and me kneeling between his legs at the edge of the bed. I slowly licked and sucked his cock, first using my hands, then letting go and sucking him hands-free. I had to, because while I was blowing him, I was trying to get the strap-on out from under the bed. I retrieved it, put it on, and even lubed it up without making a sound. Brent was none the wiser, just enjoying a good blowjob, albeit a rather traditional one. I could tell he was in the mood for ass play, as he lifted his legs and grasped his butt cheeks. I bent lower and lovingly tongued his butthole. He moaned and asked for more. I tongued him harder, lubing him and trying to tease open his hole. I finally lifted a pre-lubed finger from my strap-on preparations and slid it into his puckered butt. He grunted and grabbed his cock. I fingered him with increasing intensity. Brent was loving it.
I slipped another finger in, and Brent laughed. He bucked against me and called me a dirty girl. I fingered him harder, and he pounded his cock in equal ferocity. Finally I couldn’t stand it anymore. My fingers still working into Brent’s butt, I got up into a squat. I looked down at the small but lovely rubber dildo that stuck out from my pussy, and I nearly came right there. I couldn’t wait to give it to Brent as a complete surprise. I took his hand from his cock and took over the motion. He grabbed his legs with both hands to keep them up. My fingers continued to invade his ass. I pulled them out suddenly. Brent seemed surprised. I took the well-lubed dildo in my newly liberated hand and aimed it at his now-opened butthole.
Brent squirmed wildly when I pushed the strap-on quickly into his gaping asshole. He looked up in shock at my smiling face, and when I realized what it was and that I was now fucking him in the ass with my very own cock (okay, not really MINE, but close enough), he relaxed and smiled. No words were exchanged. Brent held his legs up and out. I jacked his cock and cupped his balls while I slid my strap-on smoothly into his tight little butt. For his part, Brent seemed positively entranced. I fucked him for probably 10 minutes before he finally came. And he came hard. His cum shot across his chest and beyond, disappearing over his shoulder and into the carpet next to the bed. I lay across his chest, rather exhausted from all my thrusting. I finally understood why men get so lazy after sex.
Eventually, I got up. The dildo slid out of his ass with the sucking sound of a boot stuck in mud. It was actually quite funny, and we laughed as we cleaned up. I was feeling happy to have given Brent such an amazing orgasm, but I was still incredibly aroused, and wanted satisfaction. Brent went into the bathroom to shower. I lay back down on the bed. I took out the butt vibrator, realizing I’d not had a chance to use it on Brent yet. I turned it on and slid it into my own ass. It throbbed inside my rectum, electrifying my clit. I produced the other dildo and started to masturbate with it. I was driving myself to a delicious orgasm when I heard the water turn off. Brent emerged seconds later, still completely nude. His eyes went wide when he saw me toying myself in both holes. His cock hardened in three seconds. He stepped over and pulled the dildo from my pussy. He kissed me wetly on the lips. He then knelt between my legs and slipped his cock into my pussy. I had long since gone on the pill, so the need for a condom was no longer. It felt so great to have him inside me, filling me up. The toy in my ass continued to hum. He remained upright, pumping his hips as he slid into me. He then reached behind him and found the end of the butt vibrator, and began to work it in and out and in different directions. So now my boyfriend was fucking me in my pussy while he worked the vibrator in and out of my ass. I was in heaven. I finally came to a screeching orgasm, pushing myself hard against him, feeling his cock fill up my pussy and the vibrator jam deeply into my ass. I came hard, and Brent came a minute later, pumping his hot cum deep into my hungry pussy.
We’ve had a lot of fun with pegging after that, finding new and interesting ways to explore each other. And I love the feeling of fucking my man hard with my rubber cock and watching him cum on himself. Perhaps one of these days I’ll ask Brent to fuck me in the ass!