Wedding Date

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It was friday night, and I was at a sports bar watching college basketball with my best friend, Alan. We’d grown up in the same suburban town and had been friends our whole lives, meeting in kindergarten, and taking the same classes through high school. We did everything together, slept over at each other’s houses, double dated, and were like brothers.

We went to separate colleges though, and lost touch. After graduation he moved to New York City and I didn’t see him for quite a while. When I graduated from law school I took a job at a firm in the city and ran into Alan at a “fun run” in Central Park. He was surprised to see me. We went for a beer after the race and talked, really talked. When I asked why we hadn’t kept in touch, Alan was embarrassed, finally admitting that he had a secret, and was afraid to tell anyone, especially me. He took a deep breath, and told me he was gay. He was sure I would hate him if he revealed his secret. I laughed, and told him I knew, and that I’d always known. I said it didn’t matter then, and it didn’t matter now. He was surprised, then relieved, and we’ve been best friends again ever since.

That’s how we ended up in the bar watching a game between our respective alma maters. We had a friendly wager on the game and he was continuously razzing me as his team held a double digit lead throughout the second half. He kept teasing me about all the things he was going to make me do for him after he won the bet. When my team cut the lead to 5 late in the game he remained confident, pointing out that there was only 30 seconds left. He almost choked on his peanuts as he watched a 3 point basket, a quick steal, and another 3 pointer at the buzzer give me the 1 point win. Alan sat back in his chair with a shocked look on his face.

“Wow, I can’t believe I lost! Oh, man…and after all the shit I’ve been giving you! All right, lay it on me, what do I have to do to settle the bet? Wash your car? Pick up your dry cleaning?

I smiled and scratched my chin.

“Welllllll…I’ve never had a butler before. You know, someone to wait on me hand and foot for a week…or a month?

Alan groaned.

“Tell you what. Why don’t you buy the next round and we’ll call it even?”

Alan jumped up and ran to the bar before I changed my mind. He returned with a cold Heineken for me and a light beer for himself.

“Here you go buddy. Thanks for taking it easy on me. Are you sure there’s nothing else you need?”

I took a long swig from my beer.

“Aaah, that’s good. No, I’m ok. Wait, maybe there is something you can do for me. Do you have any single female friends who owe you a favor? A BIG favor? And they have to be available tomorrow?”

“What are you planning you perv? Like I’d subject any of my girlfriends to someone as lame as you! WAIT! This is about your sister’s wedding, isn’t it? You STILL don’t have a date? “

I blushed red. He was right.

“Yeah. The wedding is tomorrow and I don’t have a date. I was planning to go with Allison, but she dumped me last month and I haven’t met anyone nice. Now it’s way too late.”

“Why don’t you just go alone?”

“I wish I could. My sister is bugging me to bring somebody, anybody. She spent a lot of money on this wedding and doesn’t want to waste any. Besides, she is my baby sister and can’t believe that I’m not already married. I think she wants to work on whoever I bring. You remember what she’s like.”

Alan smiled. He did remember what she was like. She was much younger than them growing up, but tried to run everyone’s life, even then. She always got her way. Alan and I sat there quietly for a minute, lost in our thoughts. Finally, Alan cleared his throat and looked at me.

“I could do it. I mean, if you want…”

I was confused.

“Do what?”

Alan looked down, embarrassed.

“Go as your date.”

I özbek escort chuckled.

“I’m not sure that’s what my sister had in mind, me coming to her wedding with a man.”

“I don’t have to be a man.”

I blinked and put down my beer. Was I sure what Alan was offering?

“Do you mean…? Are you saying you want to go the wedding as a woman? With me?”

“You know I like to crossdress. We’ve discussed this. I could do it.”

I thought back to last New Year’s Eve. We had attended the same party and Alan had a little too much to drink. I had taken him home and helped put him to bed. When I went to hang up his jacket I found the closet was full of women’s clothes. Since I was pretty sure Alan didn’t have a live in girlfriend, I figured out they were his. I slept on the couch, and the next morning over coffee, a LOT of coffee, Alan told me about his life as a woman. He said he was getting very good at it and could easiy pass. Said he did it all the time.

“Well…that is an interesting proposition. But I don’t know Alan, I’ve never even seen you dressed up. I have no idea what you look like, you know, that way.”

“Don’t worry! You’ll be surprised! Besides, wouldn’t you rather go to the wedding with someone who already loves you than some stranger doing you a favor?”

That’s what did it for me. The line about loving me. I knew he wouldn’t embarrass me if he could help it.

“Well, if you put it that way…”

Alan jumped up, excited.

“You won’t regret it! I promise you! I better go, I’ve got some shopping to do! What time is the wedding? “

“Ummm, at 2 pm?”

“Great! Pick me up around noon. And don’t worry, if you don’t like what you see, we’ll call off the whole thing. I promise!”

Alan threw me into a big hug and ran for the door.

“Bye! See you tomorrow! “

I shook my head. I hadn’t seen Alan this excited in years. Only time would tell what kind of disaster I was walking into.

————

I walked up to Alan’s apartment and knocked on the door. As I waited, I considered what I should say to walk away from this plan without hurting Alan’s feelings. The door opened and I gasped. I was looking at a woman, a beautiful woman. Slightly shorter than me in heels, she had shoulder length blonde hair, a gorgeous, perfectly made up face, a lovely red silk spaghetti strap dress showing small but perky cleavage, and shapely legs in white silk hose. I was stunned.

“Alan?”

“No, Sofia.”

I blushed at my stupidity.

“Oh…ummm…sorry, so sorry! I thought you were someone else! Is Alan in?”

“No you idiot.” she said with a smile. “It’s me! But when I’m dressed like this I prefer to be called Sofia.”

I stood back and took her in. She was beautiful! No, more than that, she was perfect! She did a slow spin to show herself off.

“So what do you think? You like?”

I couldn’t believe it was Alan, I mean, Sofia. That was going to take some getting used to! She was right. It I had met her in public I would never have known. She was stunning!

“Yes, of course. My goodness! You look fantastic!”

She grabbed her handbag and a wrap for her shoulders and stepped outside, locking the door behind her.

“Then let’s not be late sweetie.”

She took my hand and led me out to my car at the curb. I opened the passenger door and she slid into the front seat. I saw a man walking by glance over to admire her as she slipped in the car and felt oddly protective. I shook it off, got into the car, and pulled away into traffic.

We got to the wedding early, and mingled with friends and family. Sofia was a natural, befriending all the ladies and charming all the men. Several family members complimented me on my delightful new girlfriend. I wisely thanked them for their kind words, azeri escort but didn’t expound.

The ceremony was typical. Sofia and I sat in the second row, Bride’s side, and had the perfect view of everything. She was the perfect companion, sitting close, holding my hand, sharing knowing looks at the appropriate moments. I was really glad she came with me.

The first hiccup came immediately after the ceremony. The bridal party formed a reception line at the front of the church and greeted all the attendees. When I got to the front of the line I gave my sister a kiss, shook the groom’s hand, and introduced Sofia. My sister turned, smiled at Sofia, then froze, a strange look on her face.

“It’s a pleasure to meet you meet you Sofia, but, I’ve got to say, you look really familiar …have we ever met?”

I started to panic, and would probably have said something stupid, but Sofia just laughed, put her hand on my arm to stop me, and defused the situation.

“No, but I met your brother when I was visiting my cousin Alan. Do you remember Alan? He grew up down the street from you? A lot of people say we look alike. I was in the city to see my cousin and this cutie was there. How could I resist that face?”

My sister visibly relaxed and smiled.

“Of course! I see the family resemblance! That’s why you look so familiar! Thank you for coming. Please enjoy yourself!”

My sister gave Sofia a hug then turned to me. She gave me a hug and whispered in my ear.

“I like her! She’s a keeper!”

We drove to the reception and went inside. I got us a couple of drinks and we found our seats. Eventually everybody arrived and the music started. When the food arrived we all sat down and enjoyed a fabulous meal. Sofia again charmed everyone at the table. I was amazed as she conversed. She was not only the prettiest person here, she was apparently the nicest, smartest and funniest too.

After dinner there were the obligatory speeches and toasts. Finally the lights were dimmed a bit and the dancing music started. After sitting out the first few dances aimed for the kids, a beautiful song was played. Sofia stood up, held out her hand and asked me to dance. I took her hand and we walked to the dance floor together. We danced and laughed and danced again. Then a slow, romantic song started. I wasn’t sure what to do, but Sofia did. She pulled me close and we swirled around the dance floor, holding each other tightly. As the last notes of the song played out, we stood there staring into each other’s eyes. I don’t know why I did it, but I did. I leaned down to Sofia’s face, pulled her to me, and kissed her softly on her lips. She wrapped her arms around my neck, pulled me tight, and returned the kiss. I don’t know how long we kissed, but it was long enough to generate applause from the watching crowd, my sister included.

With my face turning red, we walked back to our table. My hand was around Sofia’s waist. Without thinking, I let my hand slide down her back and caress her ass. When I realized what I had done I quickly pulled my hand away. Sofia gently took my wrist, and placed my hand back on her ass.

The rest of the night went by in a blur. We drank, danced, and laughed for hours. Finally the bride and groom left, the band shut down, and everyone said their goodbyes and headed home. I drove Sofia home. We were both quiet all the way home. At her apartment door we stood for a minute looking at each other. We smiled at the same time, easing the tension.

“Thank you Sofia for being my date for the wedding. It was … really great. I’m sorry for being suspicious.”

Sofia smiled.

“I should be thanking you. That was the best date I’ve had in years.”

I looked down, unsure of what I was about to say.

“That was the best date I’ve had in … ever. I’m actually kazank escort sorry it has to end.”

Sofia put her arms around me and looked me in the eyes.

“Does it? Have to?”

“Yes. I mean … well I thought… doesn’t it?”

“No. I doesn’t. Not if you don’t want it too.”

I looked in her eyes, and fell. She opened the door, took my hand, and pulled me into the apartment. She put down her bag and wrap. She turned to me. I took her in my arms and we kissed. And kissed. And kissed. Breaking our embrace, I gasped for breath.

“Wow.”

“Hold that thought baby.”

She took me by the hand and led me into the bedroom. I stood in front of her bed as she wordlessly removed my jacket, tie and shirt. Then she undid my belt and zipper. In a single motion she lowered my pants and underwear to the floor. My stiff cock sprung to life, pointing straight at Sofia. She stood up, softly stroked my throbbing penis, and planted a kiss on my lips. Then, placing her hand on my chest, she pushed me and I fell backwards, landing softly on the bed. She removed my shoes and socks, then pulled my pants off. I now lay completely naked and erect on her bed while Sofia stood fully dressed in front of me. She reached behind her back, found the zipper of her dress, and lowered it slowly. She dropped the dress off her shoulders, then stepped out of it. I moaned. She stood there in the sexiest lingerie I had ever seen. It was red to match her dress. She ran her hands over lacy red bra cupping her tiny breasts, then down her sides, drawing my attention to the tiny red panties and the garter belt holding up her stockings. Her own hard cock peaked out of the top of the panties, making me moan again. She turned to a drawer and bent over, giving me a show with her thong covered ass. It was exquisite! She turned back around with a condom and a tube of lube in her hands and excused herself to visit the bathroom.

“I’ll be right back honey, a girl needs a little privacy you know.”

I lay there, hoping she wouldn’t be long as I was about to explode. She returned quickly and climbed up on the bed and straddled me, still wearing her high heels. She began rubbing against me. I could feel her hard cock rubbing against mine, separated only by the thin silk of her panties.

“If you keep doing that I’m gonna cum right now.”

“Not yet baby, I’m not done with you yet!”

She opened the condom wrapper she was holding in her hand. She slid down my body, stoping over my groin. Placing the condom in her mouth, she wrapped her lips around my cock and deep throated me, which unrolled the condom over my member. Then she kneeled over my cock and grasped in in her hand. She pulled her panties to the side and rubbed the tip against her asshole. I could feel that she had lubed herself when she was in the bathroom and was ready. She closed her eyes, and slowly lowered her ass onto my cock. I heard her gasp slightly as I entered her, but she soon took me all the way in. She began rocking back and forth on my cock. I reached for her and pulled her to me. Our lips met and our tongues explored each others mouths as my cock slid in and out of her slippery asshole. A few minutes of this and we were both covered in sweat and breathing heavily. Sofia suddenly sat upright, threw her head back, and moaned loudly. She shuddered, and I saw streams of silky white cum squirt from her cock and soak her pretty panties. This was so erotic I came immediately, slamming my cock harder and faster into her until I was spent. We collapsed in a sweaty, cum filled pile on the bed and gasped for breath.

We must have dozed off, because I opened my eyes and found Sofia sleeping softly on my chest. I looked down at Alan, my best friend, now Sofia, my lover. I felt warm and loved. I hugged her tightly and kissed her forehead. Her eyes fluttered open, then fixed on me. She smiled shyly.

“You should probably go home baby. I think I turn into a pumpkin at midnight.”

I stroked her hair softly and kissed her again.

“If it’s all right with you, I think I’ll stay.”

“Good.” she murmured. And nestled deeper into my body, quickly falling back to sleep.