A Night with Clarissa

A Night with Clarissa

Dear Readers,

I know some of you came here hoping for more about my budding relationship with Kevin but, if you recall, I had promised Clarissa that I would tell her all about my night with Kevin while she pounded my sissy ass with her massive strap-on Big Bertha. Of course that night turned into most of the weekend but that just meant I had more to story to share. So without further ado, here is a quick story about me and my good friend Clarissa.

Almost as soon as I got in the house after Kevin dropped me off following our wonderful weekend together, I texted Clarissa to tell her that I was finally at home and that, if she wanted, she could come over to get the details of my weekend. She replied soon after that, unfortunately she already had plans with the yoga instructor she had told me about at the bar Friday night. So much had happened that it was kind of shocking to realize that it had been less than 48 hours ago. So we made plans to have dinner that Wednesday and then go back to her place for the real fun part of the evening and I settled in for a quiet night at home. I did some laundry and other household chores I had let slid the previous week and then caught up on some Netflix shows while I pondered the implications of my growing feelings for Kevin.

The next couple of days at work were a pleasant kind of torture. I only briefly saw Kevin around the building but since we were at work, we had to keep it professional, even though we both wanted to slip into the nearest supply closet and, well, you know. We did, however, text almost constantly and by Wednesday evening, three days of flirty texts had me seriously horny. After work, I raced home and got ready for dinner with Clarissa. I decided to go with cute, bordering on slutty outfit for the 'date' and chose a cute denim mini-skirt and a red polka dot halter top that showed of my flat tummy. I matched them with a pair of red strappy sandals with a low heel and some simple jewelry. Since my toes were still painted red, I painted my fingernails to match and did up a light makeup job and pulled my hair into a messy bun, tied in place with a polka dot ribbon bow to match my top. I grabbed my purse and headed out to Clarissa's house.

She was just coming out the front door as I pulled up and she pointed at her car. Whenever we out to dinner, she always drove (and paid) because, as she put it, she wears the pants in our relationship. So I wander over to her car, waiting for her to unlock it. As I slide into the passenger seat, I purposefully flashed my panties and grinned at her. She shook her head and muttered something about me being a teasing slut. I stuck my tongue out at her and giggled when she sighed as she started the car.

Now I realize that I have yet to really describe Clarissa, so here goes. She is about five feet, eleven inches tall with a slender build and decent sized boobs for her frame. Flaming red hair hangs about halfway down her back when she does not have it in some sort of updo. Freckles cover her body and I mean everywhere (I checked). She almost exclusively wears pants. In fact, the only time I have ever seen her in a dress was at her cousin's wedding when she could not get out of wearing the official bridesmaid dress. She does wear heels though. She says it is to be as tall as or taller than the male lawyers she deals with every day. All I know is, they make her butt look hot as hell and she towers over me, which I also like.

All throughout dinner Clarissa grilled me about Kevin like an opposing witness in one of her cases. As I told the story, she kept pushing for more and more graphic details, and I happily obliged her since I could see it was turning her on quite a bit. By the time I got to the Sunday morning blow job, she was squirming in her chair and I knew I was going to get a very sloppy pussy to eat out later. She had a predatory look in her eyes when she told the waiter we would pass on dessert because we had something waiting at home. She practically pulled me out of the restaurant once the waiter returned her card and I was wondering if she would be able to wait until get back to her place. On the way there, she unzipped her jeans and I could smell her pussy wafting through the car. She took my hand and slid my fingers inside her jeans and used me to rub her clit for a few moments before pulling my hand out and smelling my fingers. I swear she growled. I had only seen her this turned on once or twice before and I knew my little sissy ass was in for a serious pounding that night. Parking the car, she literally pulled me out of the passenger seat and into her house.

As soon the door closed, she dropped her jeans and panties to the floor, grabbed me by the shoulders and pushed me to my knees. I looked up and saw her pussy was sopping wet, her thighs glistening where she had rubbed her legs together in the car. I did not have much time to marvel at her obvious arousal though because she put both hands on my head and pulled me to her, smashing my face into her engorged pussy. I quickly set to work, running my tongue up and down her slit, slurping up her juices. A few rounds of that and I attacked her clit, sucking her nub into my mouth and gently nipping it with my teeth. Clarissa has a very responsive clit and when she is very turned, like that night, it stands up proudly from its hood, allowing an eager pussy eater like yours truly easy access to her orgasm button. That night, she was so turned on already it only took a few minutes of vigorous pussy licking and clit sucking to bring to an intense orgasm. Her pussy spasmed juices all over my face, thoroughly ruining my makeup and even getting in my hair.

As her orgasm subsided, she slid down the closed front door, leaning on it as she sat on the floor, breathing heavily. I crawled up to her and pulled her into a deep kiss so I could share her juicy pussy taste. She passively accepted my kisses at first but soon retook the power position and before long, she had me pinned to the floor on my back, fucking my mouth with her tongue. Her right had my wrists held together over my head while her left hand freely roamed my body. My clitty had pushed aside the thong I had on and was tenting my mini skirt up in the front. Clarissa preferred I was uncaged when we fucked since she liked to lead me around by my hard-on and I was almost always hard whenever we had sex and that day was no exception. She grabbed my clitty under my skirt and leaned back, saying, "Come Jackie, Bertha is waiting for you."

I scrambled to my feet and followed closely behind because she had a tight grip on my privates. She could be rough with me and I loved her for it. Dragging me to her bedroom by my clitty, she spun me around and pushed me on my back onto the bed, climbed on top of me, and lowered her pussy over my face, "But first, I need a few more licks," and sat down, her slit squarely over my mouth. Not being one to deny a woman's desire to have her pussy licked, I stuck out my tongue and lapped away. In this position, she was able to grind her crotch down onto my face, nearly smothering me. Luckily, she was a seasoned face rider and knew when to let up just enough for me to catch a couple of quick breaths before she sat back down again. She rode me like this for several minutes before my skillful tongue brought her to another orgasm. She flopped to her side, lying flat on the bed, staring up.

"I just love your tongue Jackie," she panted, "It really is a shame you don't have a pussy of your own because I'd make you my girlfriend in a heartbeat."

As a response, I smiled at her and slowly crawled up to her, unbuttoning her shirt as I went. Once I had her shirt unbuttoned, I slid my hands under her bra cups from the bottom and took her pert nipples in between my thumb and forefinger. As I began rolling them around, she gasped out, "Oh, you wicked little minx, you are in for it now." She sat up, shrugging her shirt of her shoulders and stood up, clad only in her bra, now slightly askew thanks to me. She walked over to her dresser and opened the special drawer in which she kept her kinky sex toys. She ordered me to her and I could tell by the change in her voice, she had transitioned into Clarissa the Domme. I knew better than to question her order or my sissy ass would soon be stinging from the spanking I would receive. I hopped up and presented myself before her, head bowed and hands clasped together in front of me.

"Good sissy," she purred, "Now strip."

Without a pause, I shed my clothes, standing before her naked as a jaybird. While I disrobed, she rummaged around in the drawer until she pulled out a pair of leather wrist cuffs that she fastened around my wrists once I was naked. She clipped the cuffs together behind my back and gestured for me kneel in front of her. I took my spot on my knees and watched as she pulled Big Bertha out of the drawer. She strapped the harness around her waist and sighed as she slid the shorter end into her pussy, an evil smile on her face the whole time. I shuddered in anticipation, knowing what was coming next. Big Bertha firmly in place, she reached down and pulled my head toward her, ordering me to suck her big fat dick.

I eagerly opened my mouth and slid as far as I could down her fake cock. Now I am an accomplished cocksucker but Big Bertha is more than I can take right away. Clarissa did not want to wait though and in moments, her hands where on the back of my head, trying to force that massive dildo down my throat. My hands secured behind my back, all I could do was kneel there and take it, gagging up a storm until it finally overcame my resistance and popped into my throat. She held it there until just before I thought I would pass out from lack of air. Pulling it out until just the head was in my mouth, she allowed a few quick breaths and then started fucking my face at a fast pace. A few minutes later, I could tell by her breathing, she was close to yet another orgasm. Shoving Bertha deep into my throat once again, she held me there as she came hard. Pulling it all the way out, she leaned against the dresser to catch her breath. Meanwhile, I was bent over, coughing and gagging, drool bubbling out of mouth while I had no way to wipe it up. She smiled down at me and using a towel she had in the special drawer, she wiped my face clean.

Unclipping my hands, she pointed at the bed and snapped her fingers. I knew what she wanted and quickly hopped on the bed, lying on the bed with my hands outstretched to either side. Clarissa dropped her bra to the floor and approached the bed, complimenting me on my eager obedience. She fastened first one wrist, then the other to the headboard and returned to the dresser. I could only watch as she lubed Big Bertha up and waggled it at me. My ass clenched, remembering the previous times she had invaded my ass with it. My clitty was leaking a steady stream of pre-cum by now, pooling on my flat tummy. Clarissa crawled up the bed from the foot, Big Bertha nearly dragging on the blanket, to come to a stop between my legs. Using her well lubed fingers, she began to open me up. I moaned as her talented finger explored my rear entrance and before long, I was humping up to meet her hand.

"Look at you, you eager beaver," she chuckled, "You little clitty is drooling all over you."

Using the hand that was not currently spelunking in my nether cavity, she wiped a big glob of pre-cum from my belly and place her fingers over my lips. I greedily licked her fingers clean, enjoying the taste of myself. After several more minutes of almost fisting my ass, she withdrew her hand and announced it was time for the main event. She applied a fresh coat of lube to Big Bertha and lifted my legs up by my ankles. Lining it up with my well lubed hole, she shoved it in straight away until her crotch was pressed against mine. The sudden fullness took my breath away and I felt like I was very close to coming, my clitty now spewing pre-cum all over my belly.

Clarissa noticed my current state of arousal, held Big Bertha still and admonished, "You know better, no cumming until I do. Now hold it in. This may take a while. After all, I have cum three time already."

Gritting my teeth, I forced myself back from the edge and took slow deep breaths to steady myself. Seeing that had my growing orgasm under control, Clarissa slowly pulled back and forth, my ass clenching tightly around her rubber cock. The sensations as she sawed away were so intense, I was afraid I might pass out. A sudden change in pace snapped me out of it as Clarissa started to fuck me with abandon, her hips slapping in to mine, filling the room with the sounds of loud, rough sex. As I struggled to hold back the rising tide of my orgasm, I could see she was getting close to her fourth orgasm of the night. Reaching down, she squeezed my balls in her hand and growled, "Cum for me Jackie. Spew that sissy cream all over the place."

That did it and soon I was erupting from my clitty like there was no tomorrow. She grabbed my clitty and pointed it at my face and I painted myself with cum from my forehead to my chin, even getting some up my nose. Coming down from her own orgasm, Clarissa dropped my legs to the bed and leaned forward over me, Big Bertha still firmly planted inside me. She then scooped my cum off my face and fed it to me. I happily accepted her cum covered fingers in my mouth and sucked for all I was worth. Finally satisfied she had gotten as much as she could, she pulled out of my ass and rolled over to my side, pulling me into a tender embrace.

"I really like fucking your sissy ass Jackie," she said sweetly, "You are such a good bottom for me."

"I really like being your bottom Clarissa," I replied, "but now that Kevin is in the picture, I don't know if I'll be able to do this anymore."

"Oh, boo," she pouted, "I'm sure he's just a passing infatuation. I've known you for, what five years now, and have you ever had a steady boyfriend?"

"You're right there," I said, thinking about all of my past lovers and conquests, "but this time is different. I think I'm falling in love with him."

"Well, he better treat you right," she said fiercely, "or he'll have me to answer to."

"You and about a dozen drag queens from Miss Blues," I chuckled.

"Hey," she said enthusiastically, "How does he feel about open relationships?"

"I have no idea Clarissa," I replied, "We haven't yet got to that part of our new relationship. We've barely had a chance to talk in person since Sunday afternoon and I'm not going to open that can of worms in a text or over the phone."

"Well, I hope he's into it when you ask him," she smiled.

Sitting up, she freed my arms from the headboard and we both got cleaned up, put on our pajamas (I keep a pair or two at her place for sleepovers) and crawled into bed. I fell asleep with Clarissa holding close, stroking my hair.

The next morning she made me pancakes.