It was a nice autumn day in New Hampshire and a few of my college friends thought it would be nice to dine at a new restaurant. The leaves were turning their bright colors and the temperatures were still in the low sixties, making it perfect evening weather.
I had pretty much been a recluse the whole semester as I spent all my time studying and had little time for socializing. I really needed a break, and I was glad my friends encouraged me to join them.
Upon arriving at the restaurant, we were met by the maître de and seated at a nice table overlooking Lake Sunapee. The sun was low in the sky, and it was promising to be a spectacular sunset. We chatted about nothing and waited for our waitress to take our drink orders. The owner came over to our table, introduced himself, asked how we were doing, and said Stacey, his newest waitress, would be serving us. He said laughingly, it was her first day and for us to go easy on her. We all smiled and laughed in return and waited for her arrival.
A few minutes later, I looked up to see this tall, slim, and very beautiful young woman approach our table. She had on a black miniskirt, white cotton button-down blouse and black stockings. She wore knee-high leather boots with low heels and had an apron tightly wrapped around her thin and lithe waist. I was totally mesmerized by how alluring she looked.
Stacey introduced herself and I immediately was attracted to her soft-spoken, but smokey voice. When it came time for me to order, our eyes met, and I felt a tingling sensation all over. She was breathtakingly beautiful, and my heart skipped a few beats. I had never paid much attention to waitresses because they were doing a job and I would never want to be impolite by making them feel uncomfortable. I ordered my steak and salad and Stacey said she’d make sure the chef made it as I wanted. She asked if it was my first time at the restaurant and I answered yes, so she then said she’d do her best to ensure I had a good experience. When she departed to place our orders, my friends teased me, saying she liked me. Deep down, that made me happy.
Stacey continued serving us and I caught myself on several occasions staring at her as she went about her business. I loved the way she walked, slightly swaying her hips, and I couldn’t help but notice how hot she was. Her long thin legs and tight ass looked fantastic in her miniskirt. She had long blonde highlighted hair that was parted in the middle and pulled back into a tight ponytail. She had bangs in the front with long tendrils dangling on both sides of her beautiful face. On one refilling of my drink, she innocently reached down and placed her hand on my shoulder and complimented me on my attire. Her touch was very casual and brief, but it gave me shivers. Her gesture didn’t go unnoticed by my friends and their teasing continued.
Upon paying the check, I was sad the night would be soon over and that I would be leaving the restaurant and Stacey. My friend Kelley said I should give her my number. Again, I never had done that before to a waitress, so I hesitated. As we were making our way to the door, I saw Stacey walking towards me. She smiled and stopped in front of me and said it was her pleasure serving me. I don’t know how I chose my words, but they just came out “Would it be too forward of me to ask if I could see you sometime?”
Stacey smiled and slipped a small hand-written note into my hand and replied, “I’d be upset if you didn’t want to see me, I was giving you hints all night.”
The next day I called Stacey and we talked for hours. She was turning out to be everything I liked in a woman. She was smart, confident, funny, and most important, she seemed to like me a lot. I asked her if I could make her dinner as she probably was tired of serving food in a restaurant. She thought that would be nice and we set the date for Saturday. I thought of nothing else but seeing her again and it was tough getting through the rest of the week.
Finally, Saturday arrived, and I prepared everything for the perfect date at my apartment. I decided on making pasta and would serve a nice red wine. At 6 pm, Stacey knocked on my door and upon opening it, I was blown away by how utterly sexy she was dressed. As a waitress, she wore sensible clothes, although very sexy in my opinion too, but this time, she wore a tight-fitting one-piece long-sleeved dress. The hem reached to the middle of her thigh, leaving her long legs beautifully on display for my pleasure. She wore four-inch black patent heels, which accentuated her beautifully shaped legs. Her hair was down around her shoulders and combed out perfectly. She smelled even more delicious as her perfume was intoxicating. She smiled that gorgeous smile and I let her in. I felt a twinge in my crotch, and it took all my control to keep an impending erection from being a distraction.
Dinner was great and the conversation never felt awkward. We talked about everything and anything and we couldn’t keep our eyes off each other. It felt totally natural and as we sipped back the last bit of wine, we stopped talking and stared into each other’s eyes. We didn’t say a word and then, suddenly, without any indication, Stacey got up and walked over to my side of the table. I pushed my chair away from the table and she commenced to sit in my lap. She leaned down and our mouths met. Kissing her felt wonderful. She wrapped her arms around my head. We stayed kissing for a good few minutes. My cock was now fully awake and pushing hard against my jeans. I lifted Stacey up and carried her over to the couch.
We continued kissing passionately and I caressed her smooth-shaven legs and firm ass. She loved my touch and after a few minutes, she had me seated on the couch and slipped down provocatively between my legs. Wow, she was taking control and I loved it. She unbuttoned my belt, unzipped my jeans, and slipped them completely off my body. She grabbed my boxer shorts as she pulled them off, so I was totally exposed from the waist down. She then proceeded to unbutton my shirt. Once that was off, I found myself sitting there totally naked with a full erection standing inches from Stacey’s face. Without any words spoken, she opened her mouth and began licking my shaft from top to bottom ever so slowly and sensually. I could tell she loved sucking cock as she was obviously very experienced.
I thought I was going to explode. Stacey was enjoying her time pleasuring me and then I felt her slip a finger down between my ass cheeks. At the same time, she lowered herself onto my cock, taking all seven inches of me into her warm and inviting mouth. The pleasure I was experiencing was like nothing I had ever felt before. It was like Stacey had some sort of secret on cock sucking that so many other girlfriends of mine never knew. She kept the pressure up and the movement of her tongue and mouth had me approaching climax.
As she bobbed her head up and down on my cock, I felt her insert her finger into my anus. She slowly moved it in a circular motion and while doing so, penetrated me deeper. The remarkedly wonderful sensation from her finger was competing with the joy her mouth was providing. I was in heaven!
Then, without any interruption to her cock sucking, Stacey inserted a second finger into my ass. Now the pleasure intensified, and I wasn’t quite sure where this was going, but I was loving every bit of it. I couldn’t hold on any longer and then I came. I came with the most powerful of climaxes ever experienced. My cock twitched with each spurt of hot cum erupting and Stacey didn’t miss a beat. She kept sucking, even harder now. She made a firm seal with her lips around my cock and didn’t allow any cum to drop out of the corners of her mouth. When my unbelievable climax was over, I lay limp on the couch. Stacey held my now softening cock for a few more minutes and sucked the last bit of cum down her throat before coming up from the floor to join me.
As Stacey got up, she reached behind her neck and unzipped her dress and allowed it to fall to the floor in a pile by her feet. She stepped out of it and then, as she faced me, I noticed she had a small bulge in the front of her black lace panties. The room was dimly lit, but there was no mistaking she had a prominent bulge. She stared down at me with a look on her face wanting approval. I looked back to her crotch, and I now noticed the head of a cock protruding ever so slightly upward from her panty’s waistline. Stacey remained silent and kept her gaze on my face. I quickly comprehended what was happening. Stacey was a transsexual and a beautiful one at that; there was absolutely no doubt.
At that very moment, without really giving it any more thought, I reached up with both hands and, putting my fingers into her waistband, I pulled her panties down and released her now-growing cock. Stacey smiled at me. I naturally felt the next step would be for me to pleasure her orally. I leaned in to service her cock. Stacey didn’t resist and as I never considered sucking a cock in my whole life, I surprisingly felt totally uninhibited. I reached out and took her now fully erect penis into my mouth. I didn’t know what to do, but lowered my mouth onto her shaft and began using my tongue to lick and suck at the same time. Stacey leaned back and moaned ever so softly, and taking cues from her, I began experimenting with different speeds, rhythm, and pressure. I reached around and grabbed her ass cheeks and caressed them. Stacey then began thrusting her cock deeper into my mouth. Grabbing my head, she now controlled my cock sucking and I was totally amazed at how much I was enjoying this new experience.
After about five minutes, Stacey released her cock from my mouth and again, with no words spoken, she reached down and guided me into a laying position. She placed a pillow behind my head and then grabbed my legs and bent them toward my chest. She had me hold onto them with my arms, exposing my anus. I felt totally vulnerable looking up at Stacey in this position. Her long flowing hair around her shoulders, beautifully shaped C-cup breasts, incredibly chiseled abdomen, and thin waist accentuated by her stiff cock was a new sight for me. Surprisingly, I wasn’t apprehensive at all. I somehow had a change of thought toward transsexuals, maybe because of the great bonding and conversation Stacey and I had or maybe it was my realization that I was probably bi-sexual. After all, I had no hesitation sucking her when presented with her beautiful cock.
On that note, Stacey’s cock was rather beautiful. It was a little smaller than mine, but it was perfectly shaped. The head was in proportion to her six-inch shaft. Her cock shaft was completely straight, not like mine as I had a slight upward curve. She had a large protruding purple vein down the center and her balls were neatly shaven and the skin clear and tight. The hair along her pubic bone was cropped short and nicely trimmed into the shape of a heart; she was spectacular, to say the least.
Stacey reached over to her purse and pulled out a small tube of strawberry-scented sexual lubricant. She applied a generous bead to the entire length of her cock. She then squirted an amount onto her finger and deftly inserted it into my waiting hole. She took her time gently rubbing the gel deep into my rectum. She then scooted forward and placed the tip of her cock at my anus. With a slight rocking of her gorgeous hips, she pushed the head of her cock past my sphincter. I felt some pain and discomfort, but after a slight pause, Stacey pushed deeper and soon, all six inches were inserted nicely and firmly in me. She held that position for a few minutes while she leaned down and began kissing me. I could taste my own cum, which was odd, but pleasurable nonetheless, and the sensation made me feel like I was ready for what I knew was to happen next. Stacey began slowly working my ass. She picked up the pace as she thrust harder and harder into me. The feeling of having a cock in you for the first time is indescribable. I was not in any pain now and I was so getting into Stacey’s movements that I felt my own cock begin to rise.
Stacey looked pleased and broke her silence. “So, I see you like this very much.” Yes, I did like this, and I didn’t want it to ever stop. Looking up at Stacey, it was extremely erotic seeing her beautiful body rocking back and forth, breasts jiggling, and hair swaying wildly. She reached down and began stroking my cock. A light perspiration had now formed on Stacey’s upper body, and it glinted in the soft moonlight entering through my living room window. Her moans were now deeper and soon, I felt her body begin to shudder. With each shudder, I felt a warm feeling deep inside me. Stacey was coming and she filled my ass to the brim with her hot cum.
If the night couldn’t get any better, Stacey lowered her mouth onto my anus and began sucking up her cum as it oozed out of me. I never had a rim job, but now I knew what all the rave was about; it was completely amazing. Stacey then lay on top of me and our mouths met. She released her cum into my mouth and with her tongue, swished it around until I instinctively swallowed. Her final act was reaching down to grab a blanket and to cover us. We fell into a very deep and satisfying sleep.
The next morning, I woke to find Stacey had left sometime in the night. She left a note on my coffee table saying, We must see each other again soon, and signed with a simple cursive “S.”