[MF] first time being pegged (long)

The thing that Sally really liked was control. She had long enjoyed tying me up and flexing her dominant side, but bringing the riding crop into the mix meant that she had a way really asserting this control. She said it turned her on to feel that much power. It wasn’t only Sally taking control, we were good at switching – I like to put her across my knee on, beating her with the crop as she squealed in pain and pleasure. I once cuffed her face down on the bed, beating her ass, eating her our and fucking her from behind. We both enjoyed swapping the submissive and dominant roles, and the strange thrills that either role produced in us was new and exciting.

Most often, the formula was to begin the session with Sally dominating me. She would use me in some humiliating way, and then I’d retaliate by drilling her like an animal while she writhed on my cock – I guess this was a way of reasserting myself after whatever submissive situation I’d been put in. Although we found lots of things we liked doing, we liked to try out new territory, and we pushed each other as much as we could. We were new to this, but we held on to the golden principle – if it felt good, it was good. This was one time when Sally took it much further than we ever had before.

One day I got to Sally’s room at college. We’d not seen each other for a couple of days, and I was frustrated. I’d had a long day, distracted by thoughts of her, and I was ready to rip her clothes off and take her roughly on the floor the minute I walked in. Sally had other ideas. As soon as I barged into her room, she stood up from where she was working at her desk, and without saying anything fastened the dog collar on my neck. This was her asserting control simply and neatly. I was immediately subdued and she then sat down without a sound to finish whatever she was doing.

I stood there feeling ignored, and without looking at me, she commanded to strip and get on the bed. I obeyed, and she came over, cuffed me hands, but, unusually, left my feet unbound. “I’ve something new today…” she said, slightly uncertainly, and covered my eyes with a mask. I felt her shift some things around the bed and a pillow was put under my butt. Then she pushed my legs up along the bed, and left me spreadeagled on the mattress.

As I lay there, I heard Sally take something from under the bed and open it. I heard some things being unpacked, then silence. Suddenly, without warning, the riding crop lashed down on my raised ass.

“Will you do what I say?”

I knew the routine now.

“Yes miss.”

“Will you submit to my command.”

“Yes miss.”

This routine was important – it was a ritual of relinquishing authority. I gave her the right to do whatever she wanted, and this would help me accept whatever it was. In the past, she’d used this to take me beyond my comfort zone and introduce me to pleasures I never knew existed. For her, asserting control gave her the confidence to explore, to do whatever she had in mind without embarrassment. If things went too far we had a safe word, but it’d not been used yet. I suspected this fact spurred Sally on to find new limits to cross.

I felt her crawl on the bed and begin to lick between my legs. She followed up to my cock and began to coax it until it was hard. With my cock in her bobbing mouth, I felt her hand begin to probe at my ass, and a finger squeezed in easily. It was slick, and I realised it was covered in lube. She rubbed more lube over my rosebud and I gasped as she slid another finger easily inside me. She’d done this before, but this time the lube showed that this time she was playing seriously.

Then she paused, reached off the bed and I felt the tip of something hard pressing against my hole. It was covered in lube so it went in relatively easily, but gradually stretched me as it progressed. Sally pushed slowly and gradually and I felt my hole contract over it. She pressed against it. Further and further it went and I could feel it disappearing inside me. This odd, but intensely pleasurable – it occasionally crossed the line of being painful, but where it reached the limit, it felt deeply exciting. Finally, it reached the hilt. I felt completely full.

I was tied up so couldn’t move, and this heightened the vulnerability. I’d had fingers pushed inside me before, but I’d never been as fully penetrated, and it made me feel odd, passive almost, but at the same time it was intensely pleasurable. Sally let my cock drop from her lips and, without a word slid off the bed and went across the room. I heard her sit down and begin to work on her computer again, leaving me naked, tied up, and with what felt like an enormous plug nuzzling my insides.

Usually I would have felt impatient, but I knew Sally was trying to push my buttons, and that her ignoring me was part of it. She already had me in a submissive state, but she wanted to go further, to erode my control by making me wait. Impatience is thinking you’re too important to kept waiting. She didn’t want me to think that, she wanted me to know I wasn’t important enough to feel impatient. By this stage in these adventures, once she had tied me up, I felt as though I had passed the key to my autonomy to her, and therefore all I could do was wait until she did with me whatever she wanted. I had to give and receive pleasure, however Sally decided.

Without sight, it was difficult to know how the minutes were passing, but I heard Sally tapping at the keyboard, and then, after a while the sound of wine being poured. She took a swig, then clothes were shed and I heard the sound of dressing. I had no idea what to expect next. Then I felt her kneel between my legs again and take hold of the plug and ease it out bit by bit. It slid out a lot smoother than when it had gone in and I let out a moan at the sensation of it slipping through my ring. I felt released and full of anticipation of whatever was to come.

The next thing I felt was something else hard, plastic at my rosebud. First I thought it was the plug again, but it had a rounder end and was coated in lube. I thought for a moment she was going to increase the size of each plug, and felt a little worried as it pushed into me slowly. It felt smooth, but was shaped differently. Then I realised from the pressure of Sally’s arms on the bed – side by side to me – that she was now straddling me. The object moved in slowly, and I took a little more, before wincing in pain. Sally paused. I knew what it was now. She had a strap on and was fucking me. Sally pushed further and stopped to let me adjust.

At the time I didn’t know what to think, my mind was on the sensation in my ass. But I did feel submissive, passive even, and this sensation pushed me further than I had been before. I had been tied up, dominated, given orders, so I already knew that I had a submissive side, and that this was a turn on. Being fucked, being penetrated like this was new, it was like our roles were completely reversed and she was the man in the relationship plunging his cock into me. Almost, at least – there was certainly something about her cock inside me that brought a wave of pleasure to me. It wasn’t just the feeling, it was the context, it was the realisation that for the first time I was actually being penetrated. This time, I wasn’t fucking, I was being fucked.

Sally eased the rest of her cock inside me, my hole easing around it. She had used plenty of lube and it now felt comfortable at the hilt. It felt enormous (later I found it was only about 5 inches long). We rested there a moment, Sally on top, her cock deep inside me, and my cock throbbing as the pleasure poured around my body. Then she reached up and pulled the mask off. We looked into each other’s eyes. She looked a little concerned but her expression softened once she saw the wonder and lust on my face. It was a deeply intense moment, and I felt cocooned in intimacy, my eyes gazing into her hazel pools, a feeling of unity, vulnerability and trust rolled into one.

After a couple of minutes, Sally began to move. I knew she would be looking at me to check she wasn’t hurting me, and I began to smile as she began to thrust, slowly at first with the small nudges, and increasingly large thrusts. The feeling of actively being penetrated each time was incredible, and she pushed it to the hilt, as the tip nuzzled against my inside. It was slightly bent and this intensified the pressure on my ass as it moved inside. My head titled upwards and a moan began to escape my lips with every thrust.

As she fucked me, Sally was curiously silent, but her eyes were fixed on my face at all times. I knew this was new territory for her but I could feel her grow into the role. We’d discussed this before, of course, and she’d declared it’d be intriguing and a feeling of power, but now it was happening she was less confident. Later she told me she needed to really focus on how to fuck, it was doing it for the first time and she had to judge how hard to thrust without feeling her cock. I realised she was enjoying when I heard her breathing increase and saw her bite her lip. Then, as though to break the silence, she began to talk dirty to me.

“How do you like my hard cock in you? Do you like being fucked?” I could no nothing but nod. To deny the pleasure that was shooting through my body was pointless. Sally began to warm into her role.

“You’re just a bitch writhing on my cock. You’re just a slut.” I knew that out of context these words seemed routine or even laughable, but at the time, they reinforced my feelings of subservience to her and I began to moan as she continued to plough her cock into me. I knew she was trying to tease me, to feminise me and to make fun of her strong male boyfriend giving up complete control to the extent that she was fucking him, showing that she was the man in the relationship. I didn’t care. I needed this.

“Tell me you want me to fuck you,” she ordered, and she suddenly stopped with her cock at the tip.

“Please fuck me,” I said.

“Tell me how you love my cock inside you.”

“I love your hard cock inside me.”

“Beg me.”

“Please fuck me. Please stick your hard cock in me. Please fuck me hard,” I pleaded. I needed this. I had no dignity left, I just wanted to be fucked. The pleasure was intense and my cock was throbbing.

Sally bit her lip as her dominance was heightened. Being stripped of dignity like this was strangely thrilling and I was feeling pleasure like I’d never felt before shooting through my body. I had got so used to the thrill of sex coming from my cock, I’d never experienced another source, and although my cock was hard it was untouched as Sally continued to ram into me. The pleasure was still coming from my core and my cock throbbed in response. The intense feeling of humiliation and submission was intensified by having to beg Sally, and this heightened the pleasure. I couldn’t return the favour, I was tied up, and could only receive pleasure, and this liberated me from feeling any responsibility or doing anything other than what Sally said.

I felt Sally take my cock in one hand. “Shall I make my bitch cum?” She intoned, hoarsely.

I nodded. I couldn’t speak. She began to jerk my cock with one hand while still plunging into me. I began to shift, to move back onto her cock as she fucked me, increasing the rate at which each thrust reached into me. My cock began to throb as she increased her movements.

“Are you going to cum for me?” She asked. I nodded. “I want you to cum hard all over me… cum on my tits as I fuck you.”

I watched her tits ripple as she thrust in, and this image added to the pleasure. I began to moan as she increased her rate, both her hands and cock moving more quickly.

“Cum for me… I love fucking you… my cock deep inside you… I love having you moan under my cock…” She knew that talking like this turned me on, and I was amazed to find how much I loved her taking on a more aggressive role. This was working, she was really pushing hard now and I was feeling the beginning of my orgasm.

“You are just my fucktoy, you’re just a slut on my cock… You’re just my bitch.”

This was incredible and my orgasm began to spread from my balls. Sally felt my cock throb in her hands and increased her thrust.

“Yes, come for me, you slut.”

She gathered pace further and as she reached the hilt I began to cum, my cock spraying. Sally kept her hand on it to direct it onto her, and thrust with her cock so that it plunged deep inside me. Like I would, she began to press harder, thrusting it deep to the hilt into my insides, as though she was coming. It intensified the pleasure, it felt like I was being massaged from inside and out. Sally began to moan in pleasure as my cum began to hit her – “that’s it, I want your hot cum on my tits” – and the pleasure washed through me.

This was a different orgasm than normal. It was deeper, stronger pleasure that seemed to emanate from my groin, from my ass, from my core and spread like a tidal wave throughout my whole body. I shook and writhed as Sally kept her cock firmly deep inside me, moaning as my cock sprayed her with my seed. One hand moved to her torso and I saw her spread my cum over her tits, moaning as she made her breasts slick and glistening, and she then raised a hand to her mouth and licked it clean.

The pleasure still throbbed through my body, but each wave was now declining in intensity, and eventually I began to come down, a glow of satisfaction flowing through my body. I lay there, my eyes locked with Sally’s, looking incredulous at what she’d just done to me. There was a pause and then, Sally slowly withdrew from my ass, her cock sliding out slowly. I heard her take the strap off, and then felt her unlock the cuffs. I coaxed feeling back into my wrists.

Finally she threw a blanket over us and crawled into bed, her head on my chest and we lay there, holding each other. I felt incredible – I’d never come like that before – but I felt almost embarrassed by the experience, as though I had been feminised, made passive. Then I remembered how deeply and intensely pleasurable the orgasm was, the intimacy of being penetrated, how fulfilled I was feeling at having crossed a new boundary, and I remembered the intensity and intimacy of staring into Sally’s eyes as she fucked me. As she fucked me. It seemed so wrong to say it like that, but it had felt so right. It was then I knew I was hooked.

Sally looked up form my chest, her hazel eyes met mine. I felt the feeling of trust and intimacy flow through me. and I could see in her eyes that it had unlocked something for her, a new domain in her sexuality that went further than her love of control. As I had become more passive and triggered new depths of pleasure from the experience, she had found a new pleasure in the heightened dominance and control. She giggled, and kissed me.

“Wow!” she said. “*That* was a bit different!”

Source: reddit.com/r/gonewildstories/comments/u884cb/mf_first_time_being_pegged_long

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