Pushing My Boundaries

Posted in: Anal Sex | Ass Play | Sex Toys

Disclaimer: While this story is a true account, there are no names included. If you are under 18 years old, please do not read as it contains a lot of adult content.

My boyfriend and I have been dating for a long time, and although our sex is great, he’s a lot kinkier than I am (or was…). He’s really into sex toys and anal play, and while we’ve tried both a few times, I never really liked either that much, and wasn’t interested in really experimenting with them further. That all changed earlier this month when I decided to push my boundaries. My boyfriend came to my apartment to find me wearing sexy lingerie, and sitting on my bed next to a bag from the Babeland store in SoHo. He was completely shocked, but instantly turned on, as I grabbed his hard cock and led him to the bed. I manipulated his cock with my fingers, letting pre-cum slowly come out, and I whispered into his ear, “I have a surprise for you tonight.”

We began kissing and groping each other, and I could feel his hands moving all over my body, massaging my breasts and moving down to my thighs. He glided his hands over my pussy, lightly rubbing my clit on each pass and occasionally slipping his fingers inside. He began to finger me, slowly teasing me to get me as horny and wet as possible. As he kept playing with me, he began kissing and sucking down my neck, past my stomach, and he stopped right between my legs. I felt his hot breath against my clit and I shuddered in anticipation of what he was about to do. I breathed in deep and felt him put his whole mouth over my pussy, licking every spot up and down. I squirmed and moaned with delight all the while thinking of what surprises I had planned for him. Then, it was time to hint where the evening would go. I slowly repositioned myself so his tongue was down by my ass. He loves licking my butt, and we do it every now and then, but this time it felt better than usual. I kept thinking of how kinky we were going to be together, how I was going to fulfill his ultimate sexual fantasy. Lost in thought, each lap of his tongue around my sensitive ass made me want more and more. He stroked my clit while his tongue teased, bringing pure sexual bliss to my bottom.

I turned over to get on my hands and knees, so he could look at my ass while he orally pleasured it. I bit my lip as he worked my pussy with his fingers, that soft tongue circling my asshole. I started to push back, hoping he would give me just a little bit more anal pleasure. I felt my ass slowly open to the stimulation, and could feel my boyfriend enthusiastically licking my most private of areas. I looked back between my legs and noticed he was stroking his cock, with his one free hand. The sight turned me on so much, I almost came and had to take his hand away from my pussy.

I looked back at him with the most longing expression, and said in a sexy yet innocent voice, “Will you please play with my ass baby, show me how much you love it?” These were clearly some of the last words he had ever expected to hear from me. I reached in the bag and pulled out some lube, slowly pouring some right onto my asshole where he could see it. He was so turned on, his cock dripped pre-cum without even being touched. I breathed in deep and relaxed as he began rubbing my asshole, circling it and gently pressing on it with his slippery fingers. It was such a yummy sensation, and I began to rub my clit slowly to make it even better. I was so horny, my ass was able to relax and he slowly slipped a finger inside.

“Unnnnnh,” I moaned with pleasure, licking my lips at the feeling.

“Does that feel good?” he asked, making sure I was okay with everything.

“Yes,” I whimpered, “Please keep going, it feels so good in my ass.” I thought saying it would be good for mentally stimulating him, but to tell the truth it turned me on even more. I felt his finger work in and out of my butt, stimulating my g-spot each time it was all the way in. My clit pulsed in pleasure as I slowly rubbed it. I could see us in the mirror, my head down and ass in the air, with my very overjoyed boyfriend teasing my behind. I thought about how naughty and kinky it was, like an adult video. It was so hot, I had completely relaxed and was ready to take things a little bit further “Put another finger in baby,” I growled as I squeezed my breast in the mirror. I could see him putting more lube on, and then I felt him carefully work a second finger inside. I was so horny, my ass quickly accommodated the new entry. “Ooooooo,” I cooed as I felt it slide back inside. I could not believe how much I was enjoying myself, never before has anal play felt this good.

I reached in the bag and pulled out the vibrator I had bought earlier in the week.

“Where did you get that honey?” my boyfriend asked with an expression of shock and glee.

“I did a little shopping this week,” I playfully replied, as I put it on low vibration and held it against my clit. It enhanced the stimulation even more, and I began to steadily moan. I even slid it inside my pussy to feel what it would feel like to have my butt and pussy full at the same time. It was one of the most exquisite sensations I have ever felt in my life, and it made me sure of what I was going to try next.

I told my boyfriend to close his eyes and hold his hands out. I got up and reached in the bag one last time to give him the surprise object of the night. He opened his eyes and stared astonished at the butt plug in his hands.

“Honey, you don’t have to do this!” he said with genuine concern.

“It’s okay,” I reassured him, “If I don’t like it we can stop.”

I was incredibly nervous; here I was a girl who normally doesn’t like sex toys or anal play, about to try both. I did not know what to expect. Going to Babeland to buy it was hard enough, but actually trying it was going to be completely different. For some reason I never liked sex toys, and an anal toy seemed way too kinky for me. The saleswoman convinced me that it would be a great addition to our sex lives, and now I was going to see if she was right.

The plug was a purple silicone one was called a Ryder, with small to medium girth. My boyfriend eyed me suspiciously to ensure I really wanted to try it. At this point I was so turned on from the whole experience and the anticipation of what I was about to do, I really did want to try.

I got on my knees on the bed, and told my boyfriend to jerk off while he watched. I breathed deep to relax and prepare myself for the new sensation. I could see myself in the mirror, lubing the plug and bringing it back towards my butt. My boyfriend slowly jerked his cock, and I could see he was amazed and incredibly turned on by what he saw. It was just what I needed to push me over the edge. With the vibrator going on my clit, I felt the soft slippery silicone at my butt hole, and I began to softly press against it. Pure ecstasy ran through me as I felt the delicious stretch of the plug sliding in. “Oooooooooooooo,” I moaned in absolute pleasure, as the plug slowly worked its way in. It felt so good, my ass swallowed it right to the base. It was one of the most delicious feelings I have ever experienced, the soft cushy object in my derriere. I could see my boyfriend fixated upon me with desire.

“Do you like that baby?” I teased, as I rubbed the vibrator on my clit and rubbed the base of the plug, “do you like to see me play with my naughty ass?”

“It’s so hot baby, I love it,” He replied, in complete amazement.

I stood up and could feel the delicious toy inside my butt, each movement sent a wave of pleasure right through me. I walked over to my boyfriend and manipulated the tip of his cock, while placing his hand on the plug. He gently tugged it in and out, making me weak in the knees with bliss.

He kissed me deeply and passionately, and then laid me down on my back. I felt him slide his cock inside my pussy.

“It’s so tight baby,” he moaned.

“That’s because I have something in my naughty ass baby.”

He began slowly sliding in and out. Each stroke felt extraordinary. I could feel his cock rubbing against the toy next door, and the sensation of being full was overwhelming. I began breathing heavily and moaning uncontrollably as he sped up, pumping me faster and faster.

“Unnnnhhhhhhh,” I whined, feeling his cock slide in and out of me as my ass tightened around the toy. “Ohhhhh baby rub my clit please, rub my clit.” He started rubbing as I squirmed in total pleasure. I could see my reflection, legs in the air as my boyfriend fucked me and rubbed my clit. Just under my pussy was the base, a subtle hint of what kinkiness was going on.

“Oh fuck…” He grunted, and I could tell he was going to come soon. He rubbed faster and faster, and as his body rocked mine, I could feel the plug teasing the inside of my ass. I couldn’t hold it any longer. Looking one last time in the mirror, I had one of the most out-of-character thoughts in my life: “I’m a hot kinky slut.” Those words repeated throughout my mind as I began to scream in pleasure. My clit and pussy pulsed uncontrollably while the toy in my ass sent waves of pleasure throughout my body. My boyfriend pumped harder and harder until I felt his hot cum inside me right as I came. I became dizzy with pleasure, coming and thinking about those words “I’m a hot kinky slut.”

It was some of the most powerful sex I have ever had, and my boyfriend and I seem closer now that we can share in his fantasy. It was a very powerful experience, and it was good to forget our daily lives and embrace the moment of pure kinkiness and desire. My boyfriend couldn’t have been more pleased, and most importantly I found that I enjoyed the experience immensely and broadened my sexual horizons. I can’t wait to do it again next week!

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Pushing My Boundaries, 9.7 out of 10 based on 6 ratings

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