Giving in to Andy

Andy, my new friend, and I were getting very close. I had been seeing him a few nights a week. He was in love with my long nylon encased legs and feet. He would gently caress them until I gave him a footjob. This was our usual routine. But he had been hinting that he wanted more. He had started feeling my ass, and I was enjoying it. I told him that I going out of town for a week, so I could clear my head and determine where, and how far I wanted this to go.

Every time I thought about where I was going with him, I thought about giving in to him. But I still had to tell Andy that I was a crossdresser. I didn't know how he might take it. And I had never let a man enter me before. We were meeting Sunday night, and it was only Wednesday, so I wasn't surprised when I found myself stopping at an adult book store after work. But I did surprise myself when I purchased a couple of butt plugs, a dildo and some lube.

When I got home, I lubed the smallest plug, and eased it into my tight hole. To my shock, I found myself enjoying the feel of it. At first it was odd, but I eventually adjusted to the feeling of it. The next night, I tried the bigger one. Again, it took a bit, but soon I was enjoying the feeling of it in me. I tried to stretch my hole out a bit, and get ready for my first cock inside me.

It seemed like forever, but Sunday finally came. I took a long bubble bath and shaved completely. I had bought a pair of Wolford pantyhose just for this night. In fact I had bought a special outfit for tonight. Including my first set of false breasts. I put on my best wig, and did my makeup a little sluttier that usual. I attached my breasts, and admired them in the mirror. They looked fantastic on me. A nice 34D. I slipped on my new white lace bra and hooked it.

Now the moment I was waiting for. I opened the Wolfords, and gently removed them from their package. I couldn't believe how soft the felt in my hands. I couldn't wait to feel them on my smooth legs. I slowly gathered up one leg, and slipped my foot into them. As I began to stretch them up my leg, the feeling was like nothing I had ever felt. They were so soft, yet supportive. And so shiny. The feeling on my other leg was just as incredible. Once I had them pulled up, it was all I could do not to cum right then. I definitely didn't want to meet Andy with cum all over my pantyhose.

I carefully continued getting dressed. I wiggled into my new dress. It was white, and snug on me. It showed lots of leg, and very nicely showcased my tight little butt. It had a nice low cut that showed some cleavage. I was feeling quite sexy. The only thing left were my new heels. White, to match my dress. But they were 5 inch heels. I had never worn heels so high before. I eased my feet into them, and gingerly stood up. I was a bit wobbly at first, but soon I was strutting around like I wore them all the time. Finally it was time for me to go. I put on a long coat, and headed off to see if I could go through with this.

When I arrived at the park, Andy was already there. I parked next to him, and he practically ran over to open my door for me. I slowly stretched my legs out of my car. Andy was starring at legs the whole time. I, on the other hand, looked at his groin. It was growing very fast, making a big bulge in his jeans. He took my hand and helped me out of my car. We walked towards the picnic area, his arm around my waist, holding me tight.

"Andy, before we start, I have to tell you something about me." I took a deep breath and was about to tell Andy that I was a crossdresser.

"Don't say anything. I know what you are. I knew from the first time we met. But you are so nice to me, and very good looking."

I was so thrilled at what Andy said that I leaned over and began to kiss him. Andy was quick to respond, and I felt his tongue pushing past my lips. I willingly accepted it, and thrust mine into his moist mouth. He pulled me even tighter into him. His hand found my thigh, and mine found his crotch. He seemed to be bigger and harder that I remembered. Andy's hand felt so right on my thigh. He gently and slowly made his way further up my thigh. Tonight I didn't stop him. As I unzipped his pants, his finger tip found my tight, little hole. I gasped a bit as he applied some pressure to it, ever so slowly beginning to go in it. I parted my legs a bit, giving him more access to me.

Andy soon had his first nuckle in me. So far I was enjoying the feeling. I really enjoyed it when he wiggled his finger inside me. I was moaning into his mouth as he continued to probe my tight hole. Andy then added a second finger, causing me to groan loudly. I gripped his cock and started to stroke it. It was so hard in my hand. But everything felt so right. Andy then moved me on top of him. More precisely, on his hard dick.

It was nestled in the crack of my ass. Andy began the slide it up and down on my soft pantyhose. I could feel his precum soaking though my Wolfords. He felt so big against me. I wanted it deep in me. I slowly got off Andy, and grabbed my purse. Andy was looking at me quizzically. I took the lube out, and spread it all over his hard on. When I finished that I looked up at him. Andy had a big smile on his face. I stood up and slipped my dress up to my waist. Then I eased my pantyhose down, just past my ass. I then straddled Andy's legs, and began to lower myself onto him.

Andy took hold of his cock, and pointed it straight up. My virgin hole made contact with the tip of Andy's cock. I was now at the point of no return. I had stopped, with his tip on the verge of entering me. Andy put his hands on my hips, holding me steady. I began to have second thoughts about this. I felt Andy begin to push my hips downward. I resisted his advances.

What happened next took me by surprise. Andy thrust upward a bit. His tip began to stretch me, and push its way in. And it felt great! I began to let him push me down on his cock. It eased in me bit by bit. Andy's cock began to stretch me as he made his way deeper. But it felt so good to have him in me. I was trying my best to relax, and let Andy all the way in. He felt so big inside me. And he kept going further and further in me. Then I screamed as he pushed me down, and I took all of him inside me. It felt like I was being split in two. The pain was incredible, but strangely pleasurable.

I made him stop, and let myself adjust to his manhood inside me. It felt so good as I began to adjust to Andy's hard rod inside my tight ass. I leaned forward and began to kiss him. Andy's hands roamed over my body as his tongue probed my mouth. My mind was filled with so many thoughts. I couldn't believe that I was actually doing this. But it felt so right. I subconsciously began to slide up and down on the cock in me. Just a little at first, but soon Andy was pounding away, with me helping.

Andy pulled out of me, and lifted me off his lap. He turned me around and bent me over the picnic table. I pulled my skirt up for Andy, and he didn't waste any time. He plunged his manhood back in my now stretched hole. Andy pushed in so hard and so deep that I was seeing stars. I had never felt so alive as I did right then. I didn't want these feelings to ever end. I was trying to get Andy as far in me a I could. And he was doing his best to get as much of his erection inside me as he could. I reached back and pulled me cheeks as far apart as I could, allowing him to get even deeper.

That proved to be too much for Andy. He thrust in me a few more times, let out a loud groan, and erupted inside me. His cock felt like it expanded, grew another inch, then I felt his hot seed spewing out. Wave after wave of Andy's cum began filling me up. Andy thrust a couple more times, then stopped as he allowed the last of his discharge to leak out. Andys cock began to get soft, and slowly slid out of me.

I pulled my pantyhose bck up. A fantasy of mine had always been to feel someone's cum dripping into my pantyhose, and now I was about to realize it. Andy pulled his pants back up, and sat next to me. I stood there as he began to feel my leg. His fingers lightly brushed up and down my thighs, sending shivers through my body.

I clenched my hole as tight as I could. I wanted Andys cum to flood the crotch of my pantyhose all at once. I swear I could feel it building up inside me. Andys hand was now caressing my ass. Then I felt a finger tip beginning to rub my, still tender, hole. Small circles, with some gentle probing. Just ever so lightly pushing my soft pantyhose in me. I felt my hole starting to quiver as I tried to hold the cum in me. Andys finger flcked across my hole and I lost control. My rear opened up, and his still warm cum gushed out. It ran into my crotch, and down the inside of my thighs.

It felt wonderful as it made its way down my legs. I was fulfilling two fantasies in one night thanks to Andy. He stood up and we started kissing again. Andy pulled me close, ad I felt him growing hard again. He pushed me back onto the picnic table. I spread my legs for him, as he undid his pants. I leaned back and lifted my ass so he could pull my pantyhose down for his waiting cock, again. I took his tool in my hand, and placed the head on my tender hole for him.

I wrapped my legs around Andy's waist, locked my ankles behind him, and pulled. Hard. Andy's cock sank into me the second time that night. This time it went in easier. Andy sank into me up to the hilt. It felt even better that the first time. Andy's hands rubbed my thighs as he slowly fucked me. Every time he pushed in me, waves of pleasure washed through my body. I don't know how long Andy was inside me, but I was in heaven the whole time.

After what felt like an eternity, Andy groaned and let loose another load of hot seamen deep in me. The feeling was just as wonderful as the first time. Except he didn't stay hard as long. Andy slipped out of me, and I pulled my pantyhose up, in anticipation of a second load in my pantyhose that night. It didn't take long. I must have been to stretched out to stop it.

We walked back to our cars, Andy's arm around my waist, while his cum continued to leak out of my back door. My thighs were smeared by the time we got to our cars. I didn't want this night to end, but I knew it was time to go. We kissed for a few minutes before I headed to my car. Andy invited my back to his place, but I politely declined. Andy suggested that I come to his place next time. I gave him my phone number, and told him I would think about it.

All the way home, I felt the remaining cum leak into my pantyhose. I had a wonderful evening, and I knew that we would meet again. I wanted to experience all those feelings again. Soon.