A Pegging For My Valentine

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“How do I look?” said Amy, coming into the bedroom and giving a slightly self-mocking twirl.

“Stunning,” I replied.

Of course, I’d be a terrible boyfriend if that wasn’t my default response. No woman wants to be told by their significant other on Valentine’s Day that they look anything less than gorgeous, regardless of whether it’s true or not. Right now, though, I had no need for a white lie or the idealised gaze of the lover. Amy looked hot. Even the most objective observer would have said that at this moment, showing off her new lingerie and blushing at my hungry admiration, she was an absolute knock out.

Seeing her like this, I knew that this had been the right Valentine’s present. I’d gone all out on making this a special romantic night in the bedroom, lighting candles, scattering rose petals on the bed, we’d already shared champagne. The lingerie was just the icing on the cake. It was just perfect on her and justified all the time I’d spent picking it out; not just as a treat for me seeing her look so sexy, so desirable (I mean, don’t get me wrong, I love her looking casual in her jeans and oversized hoodie, but showing off her curves in sensual lingerie just pushes me over the edge), but also for Amy herself. She wasn’t always as keen on those curves as me, sometimes dwelling too much on that lack of a mythical thigh gap, but today she was flaunting them. She was drawing confidence from her sensual underwear.

She was dressed in a red satin bustier with a pattern of roses in lace. The bustier, which was doing a great job enhancing Amy’s luscious curves and showing off her ample chest, had attached garters which held up a pair of crimson thigh-high stockings. But it was what was between her shapely thighs that really caught my attention as my eyes took in the full extent of my gorgeous valentine. Instead of the matching red satin panties that had been part of her Valentine’s present along with the bustier, Amy was wearing a sort of harness around her waist and between her legs. Attached to the front with an O-shaped ring was a dangling red plastic rod.

“What is that?” I said with surprise, although I wasn’t so naive that I didn’t recognise a strapon dildo. I was just that I’d never expected my very straight and pretty vanilla girlfriend to be wearing one!

“It’s my Valentine’s present to you,” she smirked, “You got me a sexy treat, I just thought I had to return the favour.”

“With that?”

“Why not? It’s something new and fun. You said the lingerie would make me feel empowered and sexy. And it does, but so does this.”

She took the scarlet dildo in her hand and waved it in my direction, thrusting her hips forward at the same time. It was simultaneously intimidating and arresting and I wasn’t sure which of those had made me go a little weak at the knees. That champagne was already going to my head.

“Besides,” she added, “I read that this could give you the best orgasm you ever had. The prostate is the male g-spot, you know, and this can help me reach it.”

“Read that where?” I asked, beginning to find that there was something definitely extra alluring about the confident, take-charge Amy that was resulting from sensual lingerie and a strapon.

“10 Ways to Spice Up Your Valentine’s Day in the Bedroom,” which seemed plausible, even if she did appear to have given this a lot more thought than a single clickbait listicle, “Apparently, pegging is becoming more and more popular all the time.”

“So, how do you feel about your Valentine’s treat?” she continued when I said nothing in response, still collecting my thoughts, wondering how exactly I did feel about it.

“It’s… certainly a surprise gift,” I admitted, “And, anyway, it doesn’t seem fair for me to give you something to wear and your gift to me is something for you to wear as well. Shouldn’t you be giving me something?”

“Oh, believe me, I plan on giving it to you alright,” she giggled, it was an infectious and enticing sound, “And when I do really give it to you, then you’ll see how much this Valentine’s present is really for you!”

My gorgeous girlfriend in sexy lingerie telling me in flirtatiously commanding tones how I was going to get it? Of course I felt more than a little turned on, even if the strapon wasn’t part of how I’d fantasised about our romantic Valentine’s evening.

“Is this something you really want?” I was still really not sure if I did, regardless of how it was getting me a little aroused to see Amy like this, “To screw my ass with that?”

“What’s important is for you to want it too. We won’t do anything you don’t want. We can take it slow. But I think this is something you’re going to really like. Don’t you trust me to always pick out the best presents?”

This was true. Amy knew me well enough that she had a knack for getting me presents that she knew I would enjoy, sometimes even if I was a little unsure about them at first! For my last birthday she got me a skydiving experience. It wasn’t something I’d ever have considered planning for myself, but it was an absolute thrill, one of the best experiences of my life. Maybe the same would be true of pegging.

“You really do look incredible, even packing that between your legs,” I admitted, “That and the lingerie, both Valentine’s presents together… You look very sensual and powerful.”

“So, does that mean yes, you’ll try it?” her eyes lit up with excitement. How could I deny her whatever she wanted when she looked like that?

“OK,” I agreed, “Let’s try it out and just see how it goes.”

Gleefully, Amy pulled me into an embrace and soon our lips were locked in passionate kisses. Her hands wrapped around my waist and pulled me tightly against her, making me feel the hardness of her sex toy pushing against my crotch. I couldn’t help but wonder how it would feel pushing up inside me. Meanwhile, however, I was just enjoying the hungry eagerness with which my girlfriend planted her kisses on me and fondled my body.

“You won’t regret this,” she said, her hands now moving down to give my ass a squeeze, “You know I’ve always enjoyed that fine butt. Now I can’t wait to nail it!”

She was right. That had always been something she liked about my body. Often when we were making out she liked to grope and fondle my ass and it was the part of me she complimented more than any other. I guess, although I obviously hadn’t anticipated it at all, that was the first step toward her newfound desire to penetrate that ass as well. Either way, her latest ass groping was causing the stirrings of arousal to grow in my groin. One way or another, I was keen to get down to action.

Amy eagerly pulled my clothes from my body, stripping me of my shirt and jeans in moments. My semi-hard cock sprung out of my boxers as she pulled them around my ankles, prompting her to give it a playful tug. She did not continue there, though, but instead pushed me back so I was sitting on the edge of the bed completely naked.

Pushing my legs wide open, Amy knelt between them on the bedroom floor. She reached forward and began to stroke my already partially aroused cock. Her lips opened and she slid the head of it between them, swirling her tongue around it. With one hand still jerking my shaft, the other cupped my balls. Slowly that second hand slid further down and between my legs until she was caressing my perineum as she sucked on the head of my cock.

It felt great getting head from Amy, looking stunning in her rose-patterned Valentine’s lingerie lit by glowing candle light. I gave my body up to the skills of her mouth and hands, so much enjoying the moment that I even forgot what else she had planned for this evening. But then I felt Amy’s hand exploring further beneath me. From stroking my perineum, a feeling that I was really starting to get into, her finger now moved to press against my hole.

The moment I felt something push up against my tight hole my carefree body tensed up, but at the same time my already aroused cock stiffened too.

“Just relax, babe,” Amy said, still licking around my firm cock.

I did as she said, tried to regain that feeling of floating in contented pleasure, and sure enough, a moment later her finger was no longer knocking at my door. It had been invited in. She had barely half an inch of her index finger pushed up inside my tight hole. But, having never taken anything up there before, even something that small felt like it filled me up. I can’t say I didn’t enjoy that filled sensation, though, that novel sense of something pushing up into me.

“Is that good?” she said, gently moving her finger in small circles inside me.

“Yes,” I sighed.

“Do you want more?”

“Mm,” I moaned in confirmation.

Amy pushed me further back onto the bed so that I was now lying on my back with my legs lifted and spread, exposing more of my ass. She reached under the bed and pulled out a bottle of lube that I hadn’t realised was there. She really had been taking the time to prepare her own take on the romantic Valentine’s evening while I had been lighting candles and scattering rose petals! She spread the lube over her fingers. Using her index and ring finger she pushed the cheeks of my ass open and ran the middle finger along my crack and back up inside my hole, lubricating me up.

The lube felt slick and cold on my bare skin and in this position on my back with my legs spread and raised I felt even more exposed. But Amy knew just what to do to make me feel good and relaxed. As she continued to stroke my cock with her other hand, her lubricated finger plunged far deeper up my ass than before, now sliding easily inside me.

If I’d enjoyed a little the sensation of being filled when Amy’s fingertip had first pushed against my hole, this was something else entirely, something far more arousing. My body felt alive like never before with the new sensation of something penetrating deep inside, exploring pleasure centres I had never until now realised I had. Amy’s fingering thrust in and out of me and it felt amazing, pushing across tender nerve endings.

Deep in my ass she bent her finger and found the nub of my prostate. As she pushed against it I thought I was going to climax right there and then, throwing my head back in a gasp of pleasure that sounded more like Amy when I was buried deep in her sweet spot. I had to take her hands off my cock to prevent her combined prostate fingering and cock stroking from making me cum before we got to the main event.

She had been right. Of course she had. She knew me so well. I hadn’t been sure at first whether I really wanted to receive her Valentine’s present. But now, just like during the skydive, I knew that nothing would thrill me more. Feeling Amy’s finger penetrating my ass made me long to give my body further into her power. If just a finger could drive me this wild, I couldn’t help but wonder what she could do if she really gave it to me. Pegging hadn’t even been on my sexual radar when I’d got up on Valentine’s morning, but it only took a finger up my hole to make it the new subject of my curious desire.

“I want you to do it,” I said, as she slid her index finger into my ass to join the first one, now penetrating me with twice the thickness, “I want you to fuck me with your strapon.”

That was all the enthusiastic consent Amy needed. She stood up, leaving me momentarily bereft as her two fingers stopped screwing my newly eager ass, and repositioned herself between my legs. Now she stood over me, lifting my legs so my ankles were at shoulder height. I watched as she squeezed out more lube and rubbed it over her scarlet strapon with the same motion that a little earlier she had used to stroke my erect cock.

Lit by the twinkling of romantic candle light she looked more beautiful, more desirable than I could ever recall. Her womanly curves and impressive chest, perfectly displayed in rose red lingerie and stockings, had never looked so sensually feminine. But it was not a submissive feminity. It a powerful kind that stood over me with my legs in the air and bare, exposed ass. Even without the red plastic rod between her legs it was clear who was in charge of giving pleasure this Valentine’s night. Amy may have looked like an ancient fertility idol with her curvaceous, candle-lit body, but that prosthetic between her legs made it clear that it was her worshipper who would be on the receiving end.

She parted my ass cheeks with one hand and took her scarlet strapon in the other. I had certainly seen much bigger dildos in the past, in fact this one wasn’t particularly giant at all, but none of those had been about to invade my ass! Of course I felt a hum of nerves even having committed to this being what I wanted. Could I take it? I was about to find out.

Amy put the head of the dildo between my cheeks and pushed it in with her hand. After a moment of resistance it slid right up inside me. She took her hand from it and thrust forward with her hips, whereupon the lubed up dildo slid right out of my ass and flopped back between her legs.

“Oops,” she giggled, “Let’s try that again.”

I laughed too and the silly, potentially embarrassing moment helped lighten the mood between us. I no longer felt a little tense about Amy screwing my ass. I felt more relaxed and fun as she repositioned the strapon, parted my ass cheeks and thrust it in with her hand once again, this time deeper.

If I thought her fingers had left me feeling penetrated, that was nothing compared to the strapon now thrusting between my cheeks. I felt completely impaled and entirely in the power of the curvaceous beauty standing over me. And that felt so good. Giving it up to the strapon pushing up inside me felt great physically in stimulating all kinds of nerve endings, but it was the mental thrill of giving my whole body up to be penetrated by my gorgeous girlfriend that really made my cock rock hard without her even touching it any more.

Once Amy had began to get a feel for controlling the flopping plastic prosthetic, she became more forceful. At first she guided it into my waiting hole with her hand, but soon she was thrusting from her hips with her hands around my waist. Pumping in and out of my ass, Amy was really screwing me now, getting into a rhythm of penetrating deep into my body, not holding back at all as she showed me the pleasure of being on the receiving end for once.

As I lay back on the bed, surrounded by rose petals, looking up admiringly at my girlfriend with her large breasts quivering in her rose red bustier, I thought that maybe this was kind of the hot Valentine’s night I’d been planning. Sure, I hadn’t been anticipating it being me among the rose petals getting nailed. I certainly hadn’t pictured, when buying the candles and roses, me, legs spread, ankles in the air, and a strapon dildo being buried in my butt by my increasingly passionate girlfriend. But it turned out that this was even better than my imagination! Nothing I could have fantasised about for that evening could have matched the sheer sensual pleasure of my gorgeous girlfriend plunging in and out of my ass.

“God, you’re hard,” Amy sighed, as she drove her strapon into my butt and simultaneously reached to grab my erect cock.

She was right. It hadn’t even needed anything touching it while Amy had been pegging my butt to remain absolutely rock solid, jutting straight up from my crotch. I barely needed further stimulation than the strapon sliding in and out of me, it just felt that good. Nevertheless, Amy started stroking my cock in time with penetrating my ass and that was enough to send me over the edge.

I had always known that a female orgasm happened differently to a male one, but I never realised that a man on the receiving end of a fucking would cum differently from when he’s the one whose cock is inside someone else. But now I discovered that for myself. This time a wave of pleasure swept over me from my prostate where Amy’s strapon was rubbing deep inside me, and right through my body, crashing out of me. Even once I’d finished ejaculating, my stimulated prostate continued to rock my body for a few incredible moments.

“That was amazing,” I gasped.

“Glad you liked it, now it’s my turn,” said Amy, already removing her strapon harness as soon as she withdrew from my ass.

She kept me lying on the bed and moved to join me. In a moment she was kneeling straddling my face. With her thighs on either side of my head, all I could see was the area between her red lace stocking tops and the mound of pubic hair beneath the bottom of her bustier. If her standing over me, thrusting her strapon deep into my ass, had seemed like a position of power for Amy, then this surely was too.

She pushed her cunt down over my mouth and I could already note how wet she was after pegging my ass. I guess it wasn’t just a treat for me. I don’t think I’d ever seen her so slick before without even being touched with a finger. As if to further prove how needily aroused screwing my butt had made her, she let out a loud moan of satisfaction as my lips brushed against her labia and I began tonguing the slit and sucking on her clit.

Amy ground against me, pushing her crotch into my face as I hungrily tongued her slick cunt. I knew she was close to climaxing, recognising how her body tensed up and her breaths became shorter and sharper. I responded by lapping more eagerly at the moist slit pressing against my mouth, keen to give her an orgasm somewhere close to as good as the one she had given me.

And then it hit. Her body quivered and she gasped and tightened her thighs around my face. Just as it had for me with her strapon in my ass, so too did a moment of pure ecstasy run through Amy’s body from my tongue up inside her cunt.

She climbed off my face and collapsed in a heap in my arms and we held each other surrounded by rose petals as our breathing became more steady and relaxed.

“That felt incredible,” Amy said, sitting up, “How was it for you?”

“Everything you promised,” I replied, “You were right as ever. A good pegging is the best Valentine’s gift a girl could give.”

“And to think, I was wondering whether to just get you a box of chocolates instead!” she laughed.

And I did too and we both fell back into each other’s arms, feeling more blissfully in love than ever before. Isn’t that really what Valentine’s Day should be about, after all?

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