tagTransgender & CrossdressersLong Time Friends First Time Lovers Ch. 02

Long Time Friends First Time Lovers Ch. 02


After that first time with my best friend, I went home and then back to school. Trying to make sense of what happened and just what I wanted. Avoiding Doug through school for I wasn't ready to come to grips with what we did, and how much I enjoyed it. I went to class and thought long and hard about that night and how good it felt. I came to the decision that because I felt so strongly about that night I should give it a chance. So school ended and Doug had left without a word. I felt like I betrayed and hurt him. Opening my locker to get my things and go home I happened to find a note:


I don't know how you feel and I bet you're quite confused on what to do. If you're willing to try, I would like to take you out to dinner and a movie, my treat of course. If not I hope this doesn't end our friendship.

Lovingly Yours


I called him up that night and asked him where we would go to for dinner. He named a local restaurant that was a bit formal. We discussed movies, still feeling the tension between us. Then the question I asked last, "What Should I wear?"

"Corey, please dress however you want, but if you want to be treated like my date you should dress for it."he replied. With that I agreed and would be at his house just after dark at about 8pm.

Over the next couple of days before Friday, I spent time getting everything I needed. Buying a small black purse, acquired a nice sandy Burnett wig from Doug's older sister, and nice spaghetti strapped blue cocktail dress. That ended just below the knee, but has a slit that went up the left side. Long enough that you could see my stocking tops.

The day had finally arrived and it was dragging out for what seemed like forever. I got home, immediately stripped off my clothes. Knowing I had a couple of hours to kill, I jumped in the shower I shaved my body again head to toe. I packed my car with my evening wear, in a nice bag. Running thru everything I needed for like the 10th time. I crawled in the car and drove to the end of the largest field on my family's farm. Where I stripped and changed into my black satin thong, matching wonder bra, my dark barely there thigh high stockings, and my beautiful blue dress. Putting on a black lace choker, my favorite strappy black pumps with the 4in heels, pulling on my wig, and trying to do a good makeup job, but not having much practice, even with the bra I had a believable pair of b cups.

Finishing with my eyeliner and mascara, bringing out the blue of my eyes, I got behind the wheel and started to drive. With the nervous anticipation I drove, feeling a bit of exhilaration as my high heel pressing on the accelerator. I drove for ten miles with butterflies to pull up to my friends/ lovers house. Getting out of the car remembering my purse, straitening my dress a final time I strode to the door with confidence. Thrilled at the sound of my heels hitting the pavement, I knocked on the door a second later I was greeted by a smiling face. It was Angie, Doug's older sister. My heart just stopped.

"My you are a hot sexy thing now!" she said," Come on in your date will be ready in a moment."

I followed her in and we sat in the kitchen and chatted a bit. She told me to wait a sec and in a blur she ran off to her bedroom and came back in a blink. She started to do some finishing touches on my makeup. She kept telling me on how beautiful I was. She then grabbed my purse and dropped a better shade of lipstick, a compact, and a little change purse in it.

Angie said, "It has some things to keep a girl safe and ready." I opened it and saw some condoms and a small bottle of lube. With my eyes still fixed on the change purse. Angie slid up next to me with one hand sliding up my thigh just as Doug walked in. We both looked at Doug, moving her hand up a little more she turned her head but her eyes were still fixed on Doug, she whispered in my ear," Just make sure he buys the movie and dinner before you let him have your dessert."

Doug offered his hand pulling myself up we walked to his truck, opening the door for me he said." Corey honey you look amazing!"

I sat there as we drove to the movies, we chatted quite a bit. But you could feel the sexual tension like a hot electric charge in the air between the two of us. I was hot and bothered, and so ready for some relief, and if it wasn't for my tight panties the world would have seen it too. We made small talk for 20 miles; I would look over and catch him checking out my legs. I knew then he wanted me again so I stretched out a little, and placed my heels in his lap. I could feel his rock hard tool wanting attention. I started to rub my pumps over his tool until he grabbed my ankle.

"Corey sweetie if you don't stop doing that I am going to have a sticky mess we will need to clean up." Doug said.

With that I pulled back and sat up and slid next to him and pulled his hand under my dress and rubbed my clitty with it. He closed his eyes a second and gave me a squeeze. I about cummed right there. We pulled into town, and got too close to the theater and straightened up a bit, I checked my makeup and refreshed my lipstick, we climbed out and started to walk to the theater. With my clit pulsing to the sound of my heels clicking against the pavement, knowing that anyone that heard them click against the pavement would turn to look; if they were on my left side they would get a look at my lacy stocking tops.

We just got past the ticket counter going to see some shootem up movie, with supposedly a lot of sex and violence, when I heard some guy call Doug's name, and I knew who it was, it was one of our good friends. Tommy, short for Thomas was in our class and knew us well, Doug tried not to bring attention to me so much, which I was glad, But Tom just had to introduce himself, and when I looked directly at him and said hi, he got this curious look on his face. Kind of that don't I know you look. It then hit him, he stepped back looked me up and down twice and asked he could get a hug. I said," why not", he pulled me close and he nuzzled up to my ear.

"Corey you make one sexy girl, if you weren't here with Doug I would have asked you out if I knew. I would love to slide this sexy dress of you sometime." Tom said.

Blushingly I replied, "If you're nice to me maybe sometime you can pull this dress off me and then maybe I will kiss this tool you have." I squeezed his dick through his slacks, which was rock hard. We pulled apart I winked at him and it was his turn to blush.

Doug offered his arm to me and we went into the movie, Tom just followed along like a lost puppy. We sat in the back in the corner, where no one bothers to look; I sat in the middle, of the two men now with me tonight. The movie started and we were thrown into the action, but after a little while I had to shift and I uncrossed my legs which turned me to sit side ways a little. So I laid my head down on Doug's shoulder, and feeling a bit bored I closed my eyes. I was rather comfortable, feeling two men touching me. My legs were pressed up against Tom's, and I was resting my head on Doug. Opening my eyes, just to see the movie had progressed to the mandatory love interest love scene that seems to happen in every generic movie.

I saw the beautiful actress stripped down to her black bra and panties and they were off to the races. I on the other hand had, in my daze of the movie, had moved my hand down to Doug's cock, and was rubbing it though his pants, he just put a coat over me rubbing him. I relaxed a bit, and kept rubbing him. Then I felt someone's hand on my knee, kind of cautiously, then a bit more deliberate, with his fingertips tracing of thigh. I just kicked up one leg to cross my legs again which put my high heel pump right in Tom's crotch. I looked over at him, and smiled, his hand went back onto my leg as he started to massage my stockings. Occasionally grabbing my ankle and rubbing my pumps into his tool. I turned my attention back to Doug and opened his pants and pulled his cock though his boxers and just stroked him slowly but we were focused on ourselves before we knew it the credits were rolling. We got out straightened up; I knew both Doug and Tom had huge rock hard tools. As we were leaving Tom walked us to the car, and he mentioned we could go down to the docks where his uncle's boat was, and being so happy and feeling good we jumped at it.

It took 10 min to get there, and by the time I was out of the truck, Tom was already on board. He offered me a hand, and we sat out watching the waves, just relaxing, Tom took control of the boat and fired up the motor and we were off again, we cruised to a nice quiet cove Tom knew about, and by that time the wind picked up and got a bit cold, so we all went below deck, not saying it was a huge multimillion dollar boat but it was a nice 30 sail boat with a full size main cabin, with bed and TV. Tom offered me and Doug drinks and I took it and walked over to the bed and sat down and just slowly melted into the bed, we drank for a time, and I closed my eyes for a min, and I could hear Doug and Tom talking quietly about me.

Tom asked all kinds of questions, how long have I been dressing? When did Doug Know? How long have you been dating? They keep the 20 questions going for a while, until I heard, "Well Doug is she good at giving head? Is she a good fuck? Doug just looked over at me and smiled Tom was caught, I was starring right at him. He looked at me and before he could utter another word, I just slid close to him, grabbed his collar and pulled him into a deep passionate kiss. When he pulled back and looked at me with a worried look on his face.

"Well do you want an answer to your question or not?" I said sexily. Before he could respond I was undoing his pants. Quickly pulling out his cock, which was beautiful, he was a good 9in long like Doug, but quite a bit thicker. He saw the look on my face, asked me if I was scared. But the only answer I gave to him was to pull him to me swallowing his cock just licking and sucking him. He just smiled and moaned when I took him all the way down to the bottom of his shaft. I pulled back just before my gag reflex kicked in. I shifted father up on the bed with my new love tool still at my lips.

Feeling Doug's hands on my legs, as he was kissing my ankles, running his hands up my legs. He pushed up my dress found my panties. He quickly hooked my panties and pulled them down. Feeling the night air against my now exposed bottom, got me a little worried being exposed, but I was soon relieved with my legs being spread. Now my exposed hole was greeted by Doug's warm tongue. Making me moan with pleasure, I sucked and kissed Tom's hot pole, just lying there busy sucking Tom and being pleasured.

Soon I could feel Tom building to climax, he pulled away and slid down my body, I was pouting, he told me to roll me over, which I did with a smile he grabbed the zipper of my dress and then slowly pulled the dress down off my shoulders, and I rolled back over and pulled my arms out of the straps and exposed my black bra, he finished pulling my dress off, exposing me in my garter belt and stockings and my hard manly clit, he quickly grabbed my ankles and put them to his shoulders, that's when Doug reappeared with some lube and a smile on his face. Tom was curling me up under him with his cock just inches away from me. Tom was just smiling, Doug handed Tom the lube who quickly lubed himself up and with Doug's spit from his tonguing administrations, and he quickly and easily pushed through my resistance. He wasted no time to bury his cock to the hilt. Making me cry out, he just moaned and then kissed my lips forcing his tongue into my mouth we kissed for what seemed like an eternity, but then he shifted and started to saw that monster tool into me. Quickly building to a frantic pace and, he soon was slashing his cum inside me. He pulled out and got off the top of me. He collapsed down next to me all spent.

But soon Doug was taking his place and he too fucked me like I needed him too, and soon was dumping his cum into me. After the hard fuck they both gave me, we all passed out.

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