I was sound asleep when she came in, and crawled into bed with me. I had masturbated twice last night after I put her to bed, but when her naked body came into contact with mine, I rose to the occasion. We snuggled for a while, she was lightly stroking my member, while I fondled her ass.
Her face was buried in my neck, and when she said my name, I could barely hear her. She said it again to get my attention. She told me that she had a big favor to ask. She hem hawed around, and just couldn't seem to get it out. Finally, I gently grabbed her shoulders, pushed her away so that I could see her face, and I asked her to just spit it out.
She got even more embarrassed, and it a very meek voice, asked if I would do her in the ass. Just as soon as she got it out, she was totally embarrassed, and re-buried her face in my neck. Of course I was going to say yes, but I hesitated while I tried to work out the logistics. She took this to mean reluctance, and started crying in shame. I had to reassure her that I had every intention of complying with her request.
We were both naked so that part was already taken care of, so we put both of my pillows in the center of my bed, placed a towel over them, just in case there was some leakage, and Jill assumed the position.
I gently started to rub lotion around her anus with one hand, while massaging her pussy with the other. This was the first time that we had done this without significant warm-up, so it seemed to go a little slower.
Eventually, her starfish started nibbling at my finger, and I slowly began to insert it. She moaned, and said something like, 'Crap that really hurts!' I asked her if she wanted me to stop, and she wanted me to continue, she just wanted me to go slowly.
I began to lightly saw back and forth, and she started moaning. When it started to get a little dry, I added more lotion. Eventually, my finger was going all the way in, then almost all the way out, and she was taking it. Her hips were grinding on the pillow, and my erection was almost painful.
She asked me to add a second finger, and all but screamed when it went in; I don't know if from pain or pleasure. Another couple of minutes of this, and I had to have relief. I quickly spread some lotion on my dick, and climbed in behind her.
I lined myself up, and started to push. It slipped out, and went down between her legs eliciting a moan. I tried again, and it slipped the other way. I told Jen that she would have to spread'em for me so I could see what I was doing.
She reached back and spread her cheeks. Talk about an erotic sight; her cheeks spread, and her brown eye winking at me. I very carefully lined up, and started to push. I had barely gone in at all, when Jen screamed, I mean really screamed.
I immediately yanked it out. It scared me to death that I had done some sort of permanent damage, but Jen wanted to try again, and asked me to push very very slowly. Also, unless she specifically asked, don't yank it back out as that hurt almost as much as going in.
She started sucking big gulps of air, I guess to control the pain. I pushed a little harder, and nothing happened unless you count the increased volume of her moans. I pushed even harder, and was rewarded when the head popped in. I froze. She was panting, crying, and frozen in place; she also begged me to not move.
Again with the panting. After a few seconds, she told me to continue, but to go real slow. Eventually with a lot of pushing on my part, and groaning on her part, it went in another inch, and again, she made me stop. Aside from the one blow-job, this was the first time that my dick had ever entered a female.
I was so randy by then that I just wanted to shove it all the way home, and fuck the living daylights out of her. I controlled myself, and did some heavy breathing of my own.
Eventually, she let me continue, and I went in inch by blessed inch accompanied by mews, and cries, squeals, and hiccups. She was in pain, and loved it. Her ass was squeezing my dick so hard that I was in pain, and loved it as well.
Eventually, my public hair came in contact with her beautiful ass, we just lay there panting. I looked down, and the sight of her anus fully gripping my dick almost put me over the edge.
Finally, she agreed that I could start moving, but very gently, I started moving back and forth, accompanied by cries and whimpers. As this went on, I was losing more and more control, and my thrusts became more and more rapid. Of course they were firmer as well.
As much as I wanted to be a complete gentleman, eventually, I couldn't control myself, and I started to savagely fuck her ass. She was crying, shaking her head back and forth, and saying no over and over again, but I just couldn't stop; it was like I had been taken over by a demon.
I finally felt my come about to boil over, and rammed into her as hard as I could, and splashed her insides. When I came, I shoved to hard that I think that I found new territory in there, and Jen wailed.
As soon as I came down from my orgasmic bliss, I realized what I had done, and was totally embarrassed. I was still buried to the balls in her ass, and she was sobbing uncontrollably, and saying my name over and over again.
I wanted to yank myself out, and go run and hide, but that didn't seem reasonable, so I just lay there and started rubbing her arms and shoulders. Eventually, her crying subsided, and between hiccups, she thanked me.
I couldn't believe my ears, what was she thanking me for? I had savaged her, she should have been really pissed off; instead she was thanking me. When I finally pulled out, she ran to the bathroom so that she wouldn't leak anyplace, came back with a warm washcloth to clean me up with, and gave me a kiss. We snuggled for a while, and started dozing. We decided that we were at risk of going to sleep, and getting caught, so she went back to her room.
Yesterday, after the spanking, when Jeff had his finger in my ass, the pain was so delightful, especially when he started moving it around, that I knew what I had to try. The problem was that I wanted to gradually work up to it over time, but with my cousins coming to spend two weeks, I knew that I would either have to wait for two weeks, or do it today.
I was really in a quandary; I really, really, really wanted to do it, but I was afraid, afraid of the act itself, and afraid to ask Jeff. We had already gone way off the rails, and I was afraid that he would eventually rebel. I couldn't decide what to do.
I did the only thing that seemed reasonable to me; I padded down to his room, in my birthday suit of course. I crawled into bed with him, and then completely lost my nerve. I just snuggled up and started to stroke him, thinking that I would give him the blow job that he so desperately deserved.
He started fondling my ass, this started my engine running, and, even though I had decided against it, I blurted out his name with the intent of asking him. When I had his attention, I again lost my nerve. Finally he grabbed me by the shoulders, asked me what was going on, and I just blurted it out.
He didn't answer right away, and I just knew that I had crossed the line; I buried my face in his neck. Again, I was embarrassed to the max. Finally, he said that he would do it.
I was too ashamed to do anything; Jeff took charge. He put pillows in the middle of his bed, a towel on top, and had me lie face down. He started massaging me front and back, and it was wonderful. He was rubbing my anus, and I loved it.
Again, without me intentionally doing anything, it started to expand and contract. When Jeff inserted his finger, it felt like a hot poker had been stuffed in there; I cried out in pain. I begged him to take it slow and easy. Eventually, he has his whole finger in, and the pain began to subside. Jeff's dick wasn't huge, but it was a lot bigger than his finger, and I knew that some more stretching would be required. I asked him to add another finger, and when he did the pain was deliciously unbearable---almost. I did scream though.
Remember that I'd been spanked very thoroughly the day before, and my ass was still very sore and blistered. All that rubbing around back that added another component to the pain.
When Jeff decided it was time, he removed his fingers, lubed up his dick, and tried to put it in. Twice he missed the mark, and then asked me to spread my cheeks. This reminded me of yesterday when I imagined that we had an audience, and it was an even bigger turn-on. Just thinking about people watching was incredibly erotic.
I was harshly snapped back to reality when Jeff's dick popped in. I screamed, my head came back, my legs came up and I tried to push my ass forward to get away. The pain was so unbearable that I started panting just trying to control it. Eventually, I was able to allow him to continue, and each inch was a wonderful new adventure in pain.
Eventually he bottomed out, and we just lay there with him buried to the hilt. I knew it wasn't possible, but I felt like I could feel every pubic hair on my very sore ass. Once the pain subsided to a reasonable level, Jeff started moving back and forth very gently. It occurred to me that I was actually getting fucked for the very first time.
This gentleness went on for a short while, but eventually Jeff's hormones got the better of him, and he started to speed up. Before I knew it, he was pounding me so hard that I thought that the bed might break.
The pain mixed with the pleasure and pure nastiness of what we were doing started to have the desired effect. I was pretty sure that my ass would never be the same again, but I was also having orgasm after orgasm.
Finally, he rammed into me as far and as hard as he could, and announced that he was coming. The pain and pleasure were so intense that I was crying nonstop. When I finally got myself under control, I thanked him. In that moment, I felt closer to him than I had ever felt. I couldn't explain it; I just felt that way.
We snuggled, and I wanted to do that all day, but we started to doze, and we felt like I'd better get back to my room in case someone came home.
I went to bed, and went to sleep smiling with the most delicious pain both on my ass cheeks, and my anus.
TO BE CONTINUED
E-mail Quinn at [email protected] for an answer
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