She said: From Crappy to Happy

I was feeling pretty down and more than a little insecure when L met me in the parking lot at his office. I followed him inside and we started setting up. I didn't take my coat off right away - we had talked about possibly smoking a joint before playing this day and I was waiting to see if L still had that in mind because I didn't want to ask. When he removed his coat, I went ahead and took mine off, but still just stood quietly while he moved around turning on lights, etc. I guess he realized I was a little quiet and he came over and gave me a big hug and we started to kiss quite passionately. I needed to feel him - I pulled his shirt out of his pants and slid my hands up under his shirt to stroke his back, but it wasn't enough and I hastened to unbutton his shirt. He broke the kiss and started doing the same to my shirt and he talked to me softly as we undid each others' buttons.

After some more kissing and caressing, L turned away to remove the rest of his clothes and I did too, but still I hung back. He lay down on the blanket, opened his arms to me and said, "Come here." I went into his arms and we kissed and cuddled for a long while before things started to heat up. L wanted to play with the slut paddle a bit, still after that elusive complete and perfect imprint. He lined it up and asked if I were ready. Giving him the go-ahead, I braced myself for a single lash and instead got three in quick succession on my right butt cheek. By the third stinging lash in as many seconds, I was a little overwhelmed, but did he stop there? No! He immediately applied three more lashes in quick succession to my left butt cheek. It took me a minute to catch my breath and he said he was surprised I didn't scream. We had the same result as before....a very faint, if at all visible S, followed by a clear LUT. L was surprised later in our play to find that the areas of impact were quite hot to the touch in comparison with the rest of my ass.

L asked me if I'd like to climb on top and ride him. Yes, please! After fitting him with a condom, I lowered myself onto him and with our hands linked, I rode him hell-for-leather until my panting turned into loud moaning as I came hard. I had to take a minute to recover before I could continue, but it didn't take long before I had L moaning and professing his enjoyment as he too crossed the finish line. I snuggled in beside L and we lay holding and caressing each other, sharing kisses and pillow talk. He asked me if there was anything special I wanted to do next. I thought about it a bit and finally asked him if we could try anal sex. He was quiet for a minute and I backed down a bit and suggested some other things we could do instead, but then he said we could try anal, but he'd need a little more recovery time first.


L and I had been working up to anal for some time now. A few weeks before, we had tried anal in the motel room and it was very good. I mentioned it in our post at the time, but I didn't really get too into the details, because I felt that the position we were in did not allow for deep penetration and I was still afraid that in a more open position, I wouldn't be able to do it. Those of you who are regular readers will know that I have had a single experience in my past, but a terribly violent one and the fact is, I was still very afraid of the act. So even though we had already had anal sex once and it was pain-free and in fact a really good experience, I had convinced myself that that was an anomaly and that in a position with more penetration, I would not be able to do it.

I think L understood that I needed the full experience and he sent me to bend over the table, as he thought standing would be best both for his comfort as well as enabling him to have better control should it be required. He gathered condom and lube and followed. He dripped lube down the crack of my ass and inserted a finger. When I was comfortable with that, he moved to two, then went on to lube up his cock. He ran his cock through the lube on my ass and slotted the tip of his cock into my pucker. He started to penetrate and I started to freak out. "It's hurting", I said to him. I was terrified now - almost panicking, though I really wanted to do it and I knew I could trust L to not hurt me. He stroked his hands down the side of my body and gently told me to relax. He pushed in a little farther as I struggled to relax. The head of his cock in my ass now, he stopped right there and didn't move any further. He bent over me and kissed my back and ruffled my hair then smoothed his hands down my back, crooning soft words as he kissed my back over and over. I finally felt my body let go and relax completely and he felt it too, because that's when he started to move. There was no more pain. He asked often if I was okay....and I was. L now pointed out that I was still okay....and he was in me to the hilt.

L started moving with more rhythmic strokes and gaining confidence now, I started moving in the opposite rhythm, pushing back against him with every stroke. Quite comfortable now, my fears forgotten, I whispered, "Fuck me harder", and he picked up the intensity. He reached his hands under me and took my tits in his hands, never slowing his pace. I moaned. "Pull my hair, baby." I felt my head yanked back as he pulled my hair and fucked me even harder...the slapping of his hips on my ass pushing the table into the wall over and over again. I could feel my juices running down my thighs as I experimented with tightening my ass muscles to try and increase his pleasure. His reactions told me I was on the right track and it wasn't much longer before he came.

He pulled out and immediately I turned to hug him. He held me for a moment, kissed the top of my head, then moved away to clean up....he probably didn't notice, but I was very emotional and almost in tears, though I pulled myself together very quickly. I was so happy that he didn't stop when I panicked - or I may never have tried again. Instead he was so gentle, caring and understanding and guided me through to make it a great experience for me. I think I can say with confidence that I'd to it again - and like it - and even better, I even feel that though the memory of that brutal experience from my past will always exist, those negative thoughts are no longer linked to the act itself.

I went and lay down on my back on the blanket and he snuggled in beside me lying on his side, his free arm around me. More pillow talk followed as we caressed and rubbed against each other, I felt L's cock getting hard again. Donning another condom he moved over me and slid home. Man, it never stops getting better. From the first stroke to the last, he hit all the right places and I came hard. The orgasm went on and on - I swear I was in orgasm for at least 20 seconds and it took me ages to recover. In fact, before I was even fully recovered, L was cumming too. We stayed as we were for a couple minutes, L moving in me slowly while we kissed and just tried to catch our breath. After he pulled out and moved to my side, he checked the time. We'd have to leave soon.

We started packing up and as I moved around on the blanket, I realized there was a massive wet spot on the blanket where I had been lying - not just damp, but completely saturated. It was so soaked that my hand came away visibly wet when I touched it. We laughed over that and even wondered if that was just regular girl juice or if I had squirted to cause such a puddle. Either way, it was testament to the rocking sex L had just gifted me.

We finished packing up and I followed L to his office to drop off the mischief bag and then to our cars, where we parted with a hug and a kiss. I felt immeasurably happier than when I arrived. I was so sleepy on the way home, I had to open the window, but I drove with a smile, not even minding the sting of cold air on my cheeks. What a great day!