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I rolled us over so that we were both on our sides, facing each other and still embracing. As we lay there, limbs entwined and skin stuck together from sweat and fluids, we kissed slowly and softly for some time, enjoying the bliss of our first round of fucking. After a while, I gently pulled away from you and stood up at the edge of the bed. I walked over to the chair in the corner, where I had left my bag previously when I had arrived ahead of time to check-in to the room before picking you up at the airport. I rummaged in it for a moment as you watched me; when I turned around, I had a medium-sized satchel in my hand, black and velvety. I smirked at you as I walked back to the bed.
“Take off the rest of your clothes.” I instructed as I set the satchel down on the bed next to one of the pillows. You obeyed, sitting up to remove your shirt and then quickly unclasp your bra and toss them both across the bed and onto the floor. You turned and looked at me as I opened the satchel and reached a hand inside. I pulled a piece of black fabric from inside that you quickly recognized as an eye mask. Your face lit up and a fresh look of arousal passed over it. I leaned over and slid it over the top of your head and put it in place. As your world turned to darkness, I leaned in front of you and kissed you on the lips while giving your shoulder a squeeze. You started to reach up to touch me but I grabbed your hands and pulled you up to a standing position at the foot of the bed.
“Don’t move.” I said as I released you. You heard me walk away and by the direction could tell I was walking back to the side of the bed. You could not see what I did, but I grabbed the satchel and brought it over to where you were standing. I set it in the bed, and then I grabbed you by the arms and turned you around suddenly. You gasped, and then giggled, and then let out a short moan as my mouth latched onto the nipple of your right breast. I bit down on it slightly before sucking on it and swirling my tongue around it. I felt you squirm in my grasp, but I held tightly to your arms, keeping them pinned at your sides. My mouth disappeared from your right breast and reappeared on your left, doing the same thing and causing you to moan with pleasure. After a few more moments of my mouth going back and forth between your breasts, I turned you a little more and gently bent you over with a hand on your chest and one on your shoulder until you were bent over the foot of the bed, too half resting on the mattress. I tilted your head to have your face over your left shoulder, and then before you could move your arms, I grabbed both of them and pulled them behind your back and clasped them together in one of my hands at the small of your back. You felt something soft touch the skin of your wrists as I took a piece of fabric and began wrapping it around them and tied them in a firm knot. Not right, but enough that you could not separate them.
“Does that hurt?” I asked you as I ran my fingers from your wrist if your left arm up to your shoulder, while my other hand caressed your right ass cheek.
“A little, but it’s okay.” You replied as you squirmed a little to readjust yourself. “That’s better.” You wiggled your hips at me as you smiled from under your eye mask. Suddenly you gasped as my right hand, which had been rubbing your ass, suddenly left it and came down in a fairly hard slap. “Oh! Fuck!” You cried out at the unexpected stab of pain; but a fresh burst of wetness began to fork between your legs immediately after. You groaned a little and wiggled your hips more. Another smack, this time on the other cheek, while my other hand on your shoulder pressed down, holding you in place and pushing your face a little more into the bed. My right hand did not spank you again, but softly rubbed over each cheek where it had impacted, feeling the heat swell under your skin. I ran my fingers along your wet slit between your legs and chuckled.
“I see you liked that. Perhaps I will explore more of that later.” I said as I pushed my middle finger inside you and rubbed my thumb around your clit, once again growing from arousal. Your breath grew ragged and you squirmed but did not attempt to move other than that. I pulled my hand out, and my finger, now slick with your juices, shifted upwards slightly and traced the length of your crevice between your cheeks. You gasped as you felt it pass your asshole, and I pushed against it slightly before continuing on. I reached over to the satchel and pulled out two items: a small bottle of lube and a modestly sized butt plug. I flipped the cap of the line up and squeezed some onto my fingers, rubbing it around and costing the tips of my thumb and middle finger. I then dropped a small glob of it at the top of your crack; you felt a sudden cold wetness that began to slide down between your cheeks and then a moment later felt my finger again trace the length of it. My thumb then followed the same route, but it stopped at your asshole and began to massage around it in small circles, but with slightly more pressure every few seconds and smaller circles until it was firmly pressed against your tight hole. You inhaled and held your breath, waiting for a sensation you had never experienced before. Slowly, agonizingly slow, I began to push: you began to breathe again, but short and fast as you anticipated pain and had a moment of uncertainty. I felt your body tense up.
“Shh, don’t worry, I’m going to take care of you.” I said softly but with authority. “Trust me, I know what I am doing. Just try and relax: breathe in and out slowly. If you want me to stop, just say my name.” I continued to push against your back door slowly, while rubbing your pussy with my middle and index fingers. I felt you relax, and your breathing slowed to a better pace. “I can feel your asshole give: it wants to let me in. I’m going to just keep massaging it, and you just keep relaxing. Let’s try this little toy I brought along.” I grabbed the plug and replaced my thumb with it. It was about 3-4 inches long, about an inch and a half wide at the widest part, but it had a long gradual taper to make insertion easier. I pressed its narrow tip against your asshole and began to apply pressure while moving it around in a lazy circle. I grabbed the lube and added another healthy drop right at the entrance where the toy was working.
It took a few minutes, and I backed off a handful of times to coat you with more lube. Eventually, you relaxed enough that the tip of the toy began to spread open your asshole, and it began to slide inside. You moaned out, long and loud as you felt it.
“Oh my god, it’s in my ass!” You exclaimed in wonder and squirmed around.
“Yes it is, you’re doing so good, beautiful.” I replied, reaching up and caressing the exposed side of your face with my hand. “There is still a little bit to go. You’re going to feel it getting bigger for a bit, but then it will taper down and will be all the way inside you with just the end resting against your asshole. I’m going to keep going.”
“Ok, I’m ready.” You said back to me, breathing in deeply and then slowly letting out. Each time you breathed in I would hold it at its current position; as you released your breath, I would push it a little further in. Sometimes I would back it out a little methods and then push it back in. Each time I did this you moaned and my other fingers against your push felt more wetness flow out of you. This continued for many minutes, until…
“Ok Tia, it is almost all the way in.” I told you as I pushed against it firmly. You exhaled slowly after a big deep breath and I pushed until it went over the edge and with a mind of its own, slid the rest of the way and seated its base against the outside of your asshole.
“Oh my god, I feel it all the way inside me!” You said as you wiggled side to side. You pushed against it with your muscles and it backed out slightly before going back in.
“How does it feel?” I asked as I stood behind you. You were still blindfolded, so you could not see me on rubbing my cock and applying some lube to it. I moved a little closer to you, and positioned my cock just far enough away from your pussy to not be touching.
“It feels weird, but in a good way.” You replied. “I never expected this to happen and I really like it…” as you finished that sentence I grabbed your hands which were still bound behind you and pushed my cock inside you swiftly and with one stroke all the way to the base, my balls pressed against your legs. You gasped at the sudden penetration and tensed up. I could feel the plug inside your ass as my cock slid in and out of you, and watched it back itself out a little and slip back in every so often as your muscle clenched and my cock passed by it. I held tightly to your wrists and used them as leverage to drill my cock inside you out, our skin smacking together and my balls slapping against your clitoris with each stroke. You cried out and moaned into the bed with tech thrust, your body not under your control as I pounded you into the mattress.
“You look so amazing right now with both your holes filled, Tia.” I said between breaths as I fucked you with increasing vigor. “You are taking it so well. I think you’re almost ready to get fucked in your ass. Do you want that?”
“Oh god, yes.” You said before another loan escaped your lips. “Please fuck my ass, Scott. I want to feel you in my tight little asshole. Please, I need it.” You pushed your hips back against me as I pounded forward, increasing the intensity of the thrusts. As I fucked you, I untied the strand of fabric hold your arms together. Once untied, you took your arms and laid them out across the bed above your head, still resting your torso on the mattress. I slowed down my strokes until coming to a stop and pulling out of your pussy, now dripping wet down the inside of your thighs.
I grabbed the plug and slowly pulled on it until it created the wide point and then slid the rest of the way out of your asshole, which winked and stayed spread open slightly as you clenched and relaxed your muscles. I set the plug to the side and grabbed the lube, dripping a couple of drops onto your asshole and rubbing it around, dipping my thumb inside an inch or so and stretching you out before dropping a couple more drops onto my cock and spreading it around. I pressed the head of my throbbing erection against your asshole: it was noticeably larger than the plug. You could feel it, pushing for access, while your asshole resisted and strained against its entry.
“Ohhh… oh fuck…” you exclaimed as you grabbed onto the sheets with both hands and balled them up in your fists.
“This is going to be harder than the plug, so try and relax and take deep breaths like before.” I said as I kept pressure against your butthole. “I’m going to go slow again, just tell me if you want me to stop.”
“I can take it, I think.” You replied, beginning to slow your breathing. “I want you in my ass. Let me take it all. I’m yours.”
NSFW: yes
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