Me & Shar Pt. 01 - Finding a Gem

I had called ahead for a table, so we did not have to wait, and I got the table I had requested, I the back corner and very secluded. I knew that we were early enough that they would not be seating anyone close for some time. We both sat around to the back of the table, close to each other. Shari had barely let go of my arm since our first hug. I found myself staring into her eyes rather than trying to have a conversation. She finally poked me and asked if I was going to talk to her or not. I broke my gaze and apologized for my rude behavior. I first had to ask how she came to be at the party and if she was going to keep coming.

She told me that she had become friends with Gloria at therapy about a year ago and they hit it off. Gloria had been inviting her to attend for about 6 months. She said that she had reached the point that she was finally happy with her body and was ready to show it off, and she was very horny when Gloria asked her this last time, and yes, she hoped that she would be allowed to become a regular member of your group. I told her that as far as I was concerned, she was now officially a lifetime member. We ordered some wine and our meal while continuing to make small talk.

Over dinner, I told her about becoming a widow and while dating several women and having a few guy friends as well, had finally found this group just getting a start and looking for a strong core group. It was everything I was looking for, basically a monthly orgy that had become something a little different every time. I did have to admit that last night was probably one of the widest, even though I was not able to see or hear anything. I knew that I was not the only one being pleasured. She laughed at that letting me know I was so very right with that thought.

I finally stopped talking about myself and turned toward her and placed my hand on her stockinged thigh. Now, I said, tell me all about this wonderful woman named Shari that was so kindhearted that she would leave a raging orgy just to make sure an old, overly pleasured pervert was okay. She blushed, took ahold of my hand, and slid it just a little further up the thigh and cleared her throat, as did the waiter.

We ordered a dessert to share and some after dinner drinks. Then she started her story.

She had grown up with a single mom who tried her best to be everything a mom should be, but it seemed like every step forward required a half step back first. By the time she was old enough to strike out on her own, her mother was so deep into herself that she barely noticed she was gone. Shari had gotten a job and could afford to get a place with a couple of the few friends that she had been able to make over the years. I could tell that this was difficult for her and told her that it could wait if she wanted to. She patted her eyes with a Kleenex that magically appeared from somewhere and told me that she needed to say this before we could go any farther. I just nodded, lifted her hand up to kiss it gentle. She took a gulp from her drink and looked me in deeply in the eyes.

I was not Shari growing up, I was Steven. She watched me for a reaction, what she got was a soft stroke on the cheek and a I told her that, I figured that out when you told me how you knew Gloria. She was shocked, but soon figured it out, the therapy. I had to tell her that Gloria and I dated for a brief time outside of our group, and I knew about the kind of therapy she went too. I saw her visibly relax and she continued with her story.

She worked hard and saved everything she could. She was fortunate to live in a big enough city that finding councilors and doctors and therapists was the easy part. Turning her body from an over-weight introverted boy blob to a voluptuous confident woman was the hard part. I complimented her on her achievement then asked if she was interested in continuing this conversation somewhere much more privately. Shari leaned over and giving me a peck on the cheek, said I was hoping you would ask, and told me she only lived 3 blocks from there.

I quickly paid our bill, left a generous tip, and followed her out of the restaurant, to her car then to her house. I pulled into the driveway and parked behind her. I was led into the house and told to get comfortable in the living room while she got us some drinks. I sat on the edge of a plush cozy loveseat and waited as she hummed away in the kitchen. She came into the room holding two glasses of wine, but instead of taking one, I grabbed her waist and pulled her closer to me. With her hands full, I proceeded to start undoing the few remaining buttons holding her dress together. Once opened I admired the sight of her. Her light corset helped hold her lush breasts up high, so they almost spilled out, the corset itself only helped to accentuate the curviness of her waist, not hold it in, it stopped just at the beginning of her soft full hips with garters holding up her sheer stockings.

I wrapped my arms around her and pulling her close, drank in her sweet aroma. Her womanly smell was almost intoxicating. My hands caressed up and down her back, holding her close, until my fingers (accidently?) caught the top of her lacy thong panty and sled them over her hips and let them drop to the floor. Only then did I release her enough to allow some distance between us. She let me admire her, drinking in her beauty with my hungry eyes. My hands started releasing the clasps on the corset like slowly unwrapping a delicate gift.

She remained still in front of me, still clutching the glasses of wine but her eyes were closed, letting me use her body to seduce myself. Her breathing was getting shallower, and I could hear soft moans as my hands touched various parts of her. Before the last few clasps of the corset were undone, I released her stocking from the hooks. I also spent a long time touching and caressing her legs and ass as I did so. I returned to finish opening the corset and get to see the wonderful result of her arduous work, but just before I did, I took the glasses of wine from her and set them on the table beside the couch.

I slowly opened the last clasp holding the corset in place and she opened her arms and let it and her dress fall to the floor behind her. Her body was an absolute dream. I pulled her down to my so I could caress and suckle on both of her breasts. I kissed my way down to her tummy and kissed my way around her as I turned her, pausing to also get a few nibbles and bites in on her luscious ass. I got her turned back around facing me and looking lovingly into her eyes.

She looked at me questioningly and I just nodded. All she did was just give a small squat and I was rewarded with a semi erect 6 in cock popping out between her legs along with a pair of nice sized balls to match. I gently took the balls in my hand and lowered my mouth onto her dick. I sucked and played with them until I was working over a rigid 7 a half inch nice slender dick that I could not wait to feel in my ass. After several minutes of my oral attention, Shari stepped back and told me that this was going to be a night of 'lovemaking' not just 'fucking.'

I replied, "great, let's start now" and gulped down my glass of wine. Shari took my hand and led me toward her bedroom. I stopped her on the way, and asked if she knew that I wasn't always the sub that she had met last night? She said that she was sure hoping that was the case. I gave her happy bouncy ass a quick slap and we continued toward her room.

Once in her room, she hit a switch and it was lit with soft pulsating lighting, and very sensual rhythmic music filled the air. I let my eyes adjust and take in the room. A big king bed filled one wall with mirrored closet doors on both sides. Erotic pictures were hung above the bed and on the wall opposite of it. A large, overstuffed armchair and ottoman sat in one corner. She took me to the middle of the room and began to slowly undress me and started covering my exposed skin with kisses except where it was just as easy to nibble and suck. I do not think my nipples had ever had that much attention and, yes, it did force a reaction from my already firming cock. Finally, she sat on the end of the bed and undid my pants. They dropped to the floor, and she helped me step out of them along with my underwear and socks. As she straightened back up, her hands grasped my cock.

She slowly began stroking and studying it, like she was memorizing every inch. She lifted my balls to her mouth and gently took them into her warm mouth. Working them with her tongue until I began to start leaking pre-cum onto her hand. She released them from her mouth but kept them caressed in her hand as her tongue began cleaning my juices from her hand. Slowly she lowered her hot mouth over the head of my cock and started sucking it hard while her tongue flicked across the sensitive underside.

I let her have her way for several minutes before I could take it no longer, I grabbed her head firmly and fed my dick deep into her throat. I held her against me enjoying her throat flexing against me. I pulled her off my cock and leaned down to enjoy some good old sloppy French kissing, tongue, and all. Turning her over to her hands and knees on the bed, I knelt behind her and admired her full round ass. Gently pulling her cheeks apart, I flicked my tongue across her puckered asshole. I was met with just a little resistance before my probing felt her relax and open to me. I rimmed her until she started moaning and pushing herself against my face. I played with her pulsing cock while getting her ass ready to bee fucked.

Shari finally pulled away just enough and asked me to please fuck her. I stood behind her and lined my cock up with her hot wet ass. I slowly pressed my cock into her waiting hole. She readily opened to me, and I slid my entire length inside her. I could feel my ball press against hers as her velvety warmth enveloped my swollen dick. I grabbed her hips and pulled her up and back even more tightly to me. Her sphincter flexed around my raging cock, trying to milk the cum from my balls. I slowly started sliding myself in and out of her hungry ass.

I both wanted to stay buried deep in her and fuck her hard and fast at the same time, I opted to fuck her quick and hard for several strokes then push myself deep and let her ass milk me. After several minutes she started begging me to fill her ass with my cum. I was having trouble not giving her just that but was not wanting the lovemaking to end. I felt her hand reach between my legs and grab my balls, giving them a gentle tug and setting my climax in sudden motion.

I rammed as deep inside her as I could and blasted cum deep into her hot ass. We collapsed onto the bed, totally spent with me still deep inside her. When I was able to move off to the side of her just a bit, she quickly scooted out from under me and found my still firm dick with her mouth and finished sucking the last of the cum from my balls. I pulled her up to me on the bed and held her close kissing and nuzzling her. I started slowly working my way kissing and nuzzling down her body. I paused over her breasts, admiring their fullness and softness. My mouth found her hard nipples and I suckled greedily on them, moving back and forth, one to the other. My hand worked its way down to her tummy, caressing its softness before working its way further down to find her firm, long, thin penis. I used her flowing precum as lube and started gently jacking her. She moaned softly as I worked her over with my hand.

My mouth finally released her nipple and I started kissing my way down her writhing body, reaching her tummy where I lingered while covering her with kisses. Shari found herself not willing to wait any longer and taking my head in her hands, pushed me down to her throbbing cock. I started with just the head, flicking it with my tongue, swirling it over it, and tasting her sweet precum. I gradually took more of her into my hungry warm mouth, slowly working my way down the shaft. My hand caressed her balls, and I pressed a finger against her perinium, still wet from my saliva and cum from just a few minutes ago. As my mouth lowered further and further on her shaft, my finger started pressing into her ass. I timed it perfectly, and I took her into my mouth to the hilt as my finger entered her and touched her prostate. Her hips leapt off the bed and she grabbed my head, shoving her body hard into me. Her cock emptied into my throat as she writhed against me. I held her firm, continuing to suck her dick and massage her prostate while she filled my throat with warm tasty cum.

She went still, pressing hard into my face as her climax slowly subsided. I felt her start to relax and quickly resumed sucking and massaging, making her suddenly climax again. This time I was able to hold some of her cum in my mouth and suckle on her softening cock while waiting for her to recover. This time as she started to relax, I pulled her down to my and covered her mouth with mine, unloading her cum into her waiting mouth, which she greedily drank down. We collapsed on the bed together, snuggling and holing each other close, completely sated, for the moment.

She started to stir after several minutes. I thought that she was going to get up but instead she moved up and straddled my body. She told me that since I had shared with her, she was going to share with me. She lifted her hips over my face then lowered her well fucked ass over my mouth. I do not know how she had held it in, but her butthole opened just a little and the load cum that I had deeply placed in her ass earlier, came flowing out into my mouth. I cleaned her properly before she climbed down to enjoy it with me.

As we enjoyed a little pillow talk for a while. I had to tell her that in the last 48 hours I had done and experienced so many new things sexually that I was almost in sensory overload. She told me that I seemed to be handling things just fine, and she wasn't all that far behind me on the new things count. Sex was just so easy and uncomplicated with her, it just seemed to happen without thinking about it and we were both so open to just anything that might happen next, and I did not want it to stop anytime soon.

She did finally stand up and turned to me and sat on my stomach. She told me that she needed to use the bathroom and when I heard her in the shower, it was my turn and then join her in the shower. She popped up and left me on the bed and danced her way into the bathroom, making sure that I was watching her happy ass bounce all the way. As I waited to hear the shower, I studied the paintings on her walls. I could see a familiar face in each of them and realized that Shari was the main subject in all of them. They seemingly chronicled her transition from the place she was to begin her transsexual journey to the beautiful woman she had become, each one getting more sensually suggestive, as she and they progressed.

I heard the shower door close, so I got up and headed to the bathroom. Stepping in the door there was a sink and vanity on the right and stool on the left, straight ahead was the doorway to the shower and tub. I did peek in to watch her shower just a second before using the restroom and joining her. The shower was one of those that had enough nozzles, and showerheads to remind you of a decontamination chamber.

I also took note of the huge whirlpool tub on the other side of the room. Shari's head was covered with an old fashion shower cap, and I had to snicker just a bit. She playfully slapped my arm and said that she had spent hours on her hair and was not done trying to impress me with it just quite yet. Then she handed me a soapy cloth and told me I was just in time to wash her back, turning away from me. I lathered her back up from her shoulders all the way down to her curvy ass. She made it difficult by leaning her soapy body against me. I could not resist reaching around and giving her front some extra cleaning too.

After a bit, she took the cloth from me and started soaping down my chest, also washing lower and making extra sure that I was clean everywhere. She turned me around and started washing my back and down to my ass, teasing me by dropping the cloth and using her hands only to wash my ass. I could feel her fingers gently probing my anus as the warm streams of water cascaded over us. I sensed her it down on the bench in the shower followed by warm slippery lube getting slathered around my asshole. She pulled me back to her and slowly lowered me onto her lap. Her hard slender dick easily entered me. I sat on her lap and let her fill me with her last remaining manhood. I worked my slippery lathered ass around on her lap, trying to get as much of her into my ass as I could. Her cock rubbed my prostate as I squirmed. She reached around me, stroking my rigid dick. I leaned back, feeling her soft breasts and hard nipples pressing into me.

She stroked me fasted and harder, urging another climax from my already drained balls. Adjusting herself just a bit she was able to hit my prostate easily, I could not hold it back any longer and my sperm shot across the shower with force. She held me close to her as my climax subsided. Only when I was able to start moving on her lap again did I feel her cock swell and her own climax start. I raised up just enough that she was able to start pumping her own load deep into my ass. I could feel the warmth of it filling my rectum.

When we were both recovered enough, we finished the shower and dried each other. She produced a soft warm robe for me and a silky, barely enough to cover her robe for herself. She asked if I would like coffee and relaxing and I said that I would.

We sat at the kitchen table and enjoyed a nice warm cup of coffee. I noticed the time and could not believe that we had been having sex in one form or another for 3 hours. We chatted about this and that, never once mentioning any of the sex play that we had just performed with each other. Even with the coffee we both tired from the last couple of day and she asked me to spend the night as 4 in the morning was no time to be going home. I agreed that waking up next to her again would be a good thing as far as I was concerned.

I slept a very restful and blissful sleep for the second night in a row. In the morning I awoke to the smell of bacon and an, unfortunately, empty bed. I glanced at the end of the bed and her robe was still lying so I opted for grabbing my boxers before heading out to join her, I was overdressed. She quickly padded across the room and met me with a big hug and kiss and pushing my boxers down over my hips letting them fall to the floor. Only then did she inform me that clothing in her house was always only on an as needed basis. Her arm swept around to the huge bank of windows across the back of her house that opened out to a large open pasture with no houses in sight, although she did say that occasionally cows would stroll by and moo 'nice udders' to her and she always returned the compliment.

Being served breakfast after a night filled with sex is always a wonderful way to start the day. We again spent a long time chatting about so many topics. We did not always agree on everything but nothing that was earth shattering or deal breaking, so far. I resisted long as I could before I finally had to make my unwanted departure. I did have things that I had to get done and I am sure that Shari did also. I dressed to leave but before I could go, I had to tell her that I was totally enamored by her. I loved her personality and perspective on life. I thought that she was a gorgeous woman and I really wanted to spend as much time with her as I could. She assured me that my feelings were the same as hers and spending time together was a very doable thing. Slipping her robe on, she did have neighbors in the front, and they did keep a friendly eye on her, she tried to keep some decency to that side of the house.