“Let’s keep that there for a bit, Slave.” What could she possibly have in mind for me? She undid her strap-on and let it fall to the floor. She walked over to the wall and leaned into it, “Fuck me, Slave.” I wasn’t going to be able to do shit with my arms behind my back, so I rolled back and moved my arms underneath my legs so they were now in front of me. I stood up and took position behind my Mistress. I found her entrance and thrust into her deeply, I knew she liked that so much and it was confirmed again by her grunts.
I reached for her shoulders and held her tightly as I thrust into her. Deeper and harder, harder and faster, she began to squeak with each thrust. Breaths became shorter until there was none at all. I continued pounding her to prolong the orgasm. It did its trick as she came up for air in a deep exhale and a quick inhale to repeat the process again. Three more times she did this before crying sounds began to emanate from her, “Mistress?”
“Don’t stop!” she cried. I didn’t as long as I could. What must have been 3 solid minutes of thrusts finally came to a halt as I grew tired. My thighs ached, my ass cheeks tingled from the sweat pouring over them, I must have rubbed myself raw along the way. Never the less, I was entirely happy and satisfied. I helped her down to the floor and we laid there for some time basking in our after-sex glow.
After some time she looked over to me and said, “Did that feel good?”
“Of course, that was . . .”
“No, I mean the anal plugs, did they hurt?”
“No, not at all, you were very gentle. I enjoyed that a lot.”
She paused for a moment, “I would like to try again.”
I rolled over, kissed her lips and smiled, “Yes, my Mistress.” I kept her lying on her back to keep her most relaxed. I then placed some lube on my fingers and warmed it up for her. I rubbed it over her labia as I am sure those are a bit raw if I am, and then moved down and rubbed over her anus. Again she clenched her cheeks together, “I am going to keep doing this, no penetration, until you get used to the sensation.” She began to relax as I rubbed more and more lube into the area.
“Are you ready for the first one?” She nodded and I placed the smallest of plugs next to her anus, “Here we go.” I slowly pressed it into her, taking frequent breaks as it disappeared into her. When she had reached the base, I asked, “How is it?”
“Much better than last time.”
“Good, I’m glad.” I worked the plug in and out slowly so she could feel how it moved, “Ready for the next one?” She nodded her head and I slowly removed the first one and went through the same ritual with the next size. Slowly pressing it into her and taking frequent breaks, “I have read that it helps to play with yourself as I do this to help relax you.” She hesitated; I know that she is kind of embarrassed about masturbation. “Come on, you just did it over my gagged face.” That disarmed her and she began to slowly rub her clit.
As she reached the base of this one, she moaned, “Much better I see.” She licked her lips as she nodded. Again, I worked it in and out of her. I could see she was enjoying it. She even ceased masturbation and purely enjoyed the sensations. I continued working with this one as the next one is even a touch thicker than I am.
“Next one”, she moaned. Who was I to argue? I lubed up the last unused one, being I still had one in me, and inserted it into her. She grabbed a hold of this one and inserted it herself. She turned over onto her knees, “Fuck me again.” Gladly, I took her from behind. She surprised me by grabbing hold of my plug and moving it around. It felt great. I watched her insert be pressed between our bodies. She pulled my plug out and inserted three fingers, rubbing my prostate. If she kept that up, I was going to cum.
I pulled out, “Do you think you are ready for me?”
“Uh huh”, I then slowly pulled her insert out while lubing myself up. I slid in smoothly, no stretching, no pausing. She moaned as I pressed into her. I held against her as she got used to the feeling, then slowly moved out and back in. I slowly increased the pace, going by her sounds and body language. When she stopped rubbing my prostate, I knew some discomfort was coming on and I backed off. I tried my hardest to make this a pleasurable experience, and it seems it was working.
We worked ourselves to a rhythmic pace, her breathing was quickening. Though for this, she did not squeak as usual, this was a much deeper, guttural moan. She reached behind her and held me next to her, no thrusting, as she shuddered. I could feel her tighten around me. She let the orgasm subside then pulled away from me, soliciting another shudder. We laid next to each other in another post coital bliss.
“It’s nothing compared to a regular orgasm, but it was fun.” She kissed me, “thank you for being so gentle.”
“It was my pleasure.” Quite literally, “and if that is nothing compared to one of your regulars, I am jealous.”
*
This fantasy has been helping me get to sleep lately. Ok, so it has been more of a hindrance, but it is what helps me finish so I can sleep. If you can’t tell, I am feeling very submissive now. The first half is entirely possible; the second half is pure fiction, mainly because the other party in this fantasy has an aversion to anal play. I believe it is due to two reasons; one, anytime it is tried, pain ensues; two, when she used a toy on me, it wasn’t exactly the cleanest time. If she had half the pleasure I do when receiving, I think it would be much more common. So I hope you enjoy.