A Company Man Ch. 4

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Jack & Karen are married.
1.6k words
4.13
70.7k
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Part 4 of the 4 part series

Updated 10/22/2022
Created 12/01/2001
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I looked at the wedding dress. It really was beautiful. I knew it was for me. I also knew that if I refused to wear it, it would be senseless. I'd end up wearing it anyway. So, I looked at Susie and Nancy and said, "I guess we better get started or we'll be late!" They both smiled at me. Susie said, "Well, first things first, we need to do your hair and make-up." So, we went into the changing room and sat down at the vanity. Nancy placed a wig on my head. Then, she did my make-up. Staring into the mirror, I was quite surprised at how cute I was.

When Nancy finished, Susie told me to come over to her and she'd help me get dressed. Susie had already gotten dressed in her gown; Nancy did her hair and make-up as I went to get dressed. First, I put on a white satin merry widow. Susie added pads to the bra cup to fill it out nicely. Then, I put on a matching set of white crotch-less panties.

Then white silk stockings were added and fastened to garters, which were already part of the merry widow. Then, she helped me slip into the dress. In what seemed like minutes, I went from looking like an average guy to looking like a beautiful woman! Nancy whistled from behind me, "Wow, you look better than most women! You'll definitely turn a few heads today!" We all laughed.

It was almost time to go. Susie and Nancy finished dressing and preparing themselves. I waited patiently for them and we talked about various things from my job, hobbies, to sex. Finally, I slipped on a pair of white high heels. I almost fell on my face! Susie and Nancy started giggling. "Good thing, you'll be escorted!" I hadn't thought of that. I was being given away? By whom? As if reading my thoughts, the door opened. In walked Karen's father. He was dressed in a black tuxedo and looked quite handsome. Of course, the last time I had seen him, my face had been a lot lower than eye level. He gave a low whistle, "You look beautiful" He came over and offered his arm to me. "If we had a little more time, I'd bend you over right now!" Nancy scolded him, "Now, we'll have none of that. You'll wrinkle the dress and mess up Jackie's makeup. What would your wife say?" He looked crestfallen. He knew that if he tried anything his wife would be furious. Then, placing my arm in his, he led me out the door.

We went down the hall and went out a back patio door onto the mansion's grounds. There an elaborate wedding ceremony had been staged. All the family members were there. Standing at the end of a long red carpet stood Karen. She was dressed in a Tuxedo. Yet, even in that, she was gorgeous and sexy. She smiled as she looked at me. I could see the delight in her eyes. The music started playing and the ceremony began. Before I knew it, I had said "I do and Karen was kissing the bride, me!"

We went back down the carpet and into the house. Karen led me, still wobbly on those high heels, back to the banquet room. There a wedding reception had been prepared. The wedding cake was in the middle, but I noticed that there were no little figures on top. I laughed at that and told Karen, "Well, I doubt if you could buy figurines of a cross-dressed male and his new "husband."" Karen laughed at that and said, "But darling, we are the center pieces!'" She took my hand and led me to a round cake shaped dais. Sure enough, we were now the centerpieces of the cake. Pictures were taken of the wedding party. All in all, except that we were both cross-dressed. The wedding was normal.

It was normal until my mother-in-law came to the dais. She turned and spoke to the crowd, which became quiet.

"As you all know, Jackie is now the "wife" of my daughter, Karen. However, as it is a custom in this family, the head of the family claims first rites of the new bride." Karen turned me around and then lifted up my dress. She whispered in my ear to bend over, which I did. Then, with no warning, I felt the head of a dildo sliding into my ass. It stung and felt like it was ripping me apart. I had not expected that. The only saving grace was that the dildo had obviously been lubed and the lube quickly eased the dildo's movement in and out of my ass. I moaned. Janet, my mother-in-law, laughed and said, "Yes, Jackie, it's mine whenever I want it!" My cock was beginning to harden as I felt her slide in and out. I knew that the other end was giving her immense pleasure as I could also hear her start to moan. She reached under me and played with my balls, squeezing them in her hands. A finger slid up the shaft of my cock and then stroked the head. I could feel a little drop of pre-cum form. She took her finger and swirled it in the pre-cum and then put it to my mouth. "Lick it off, baby." I took the finger in my mouth and sucked it clean. My tongue not missing any of the cum. Janet, in a load moan, came. Her body slumped onto mine and I could feel the heat of her body pressing against me. She said in my ear, "Karen did pick a wonderful man. I'm glad you're in the family. Welcome, sweetie!" With that, she stood up, and said to the rest of the crowd. "Ok, she's all yours!"

A receiving line was formed. As each couple walked by, I was expected to service both of them. The man I would suck until he was ready to cum. Just before he squirt his thick white cum, I would take his cock out of my mouth and aiming his cock, let him squirt into a silver wedding goblet. The lady I would present my ass to. She would slide her "cock" into me and use my ass for her pleasure. I was then expected to lick her pussy clean. Each lady that way would cum twice, while each man but once. Karen stood by me, smiling and accepting congratulations on finding such a beautiful wife. In all, there were 30 couples and several single men and women attending the reception. I had thought there were only 15 couples on the Company's board. Karen told me I was right, these other people were friends of the family and that I was to treat them always properly.

Finally, the line cleared and there was only one last person, my father-in-law. He stood for a second and then turned to face the crowd. "As my beautiful wife was first, so I am last. Jackie, let that also be a lesson to you." Having said that, he offered his cock to me. I took it in my mouth. My jaw was beginning to ache. Nether-the-less, I gave him the best blow job of the evening. He was groaning in delight as I licked his balls, sucking them one by one into my mouth. He shuddered as my tongue slide up and down the shaft and then lapped at the soft underside of his cock head. Then, I opened my mouth wide and let his cock slide deep inside my throat. He got so turned on that he grabbed my head and started fucking my mouth.

"Daddy, shame on you! You know the rules; you can only stand there!" Karen was livid. Janet, who was standing next to her daughter, reached over and pushed her husband back. "Don't spoil it, Nicky. It's your daughter's wedding day." His cock started to jerk and I quickly lifted the goblet to it. Using my hand, I milked him dry, just as I had done the other 45 men. Finishing the reception line, Karen told me to stand up, which I did. My dress fell back down in place.

Nancy and Susie had been quietly at my side, greeting people and helping them position themselves for me to service. As the reception line was finished, I felt their hands on me. They removed my dress. I now stood in front of almost 100 people in lingerie. My cock was standing out straight and hard, through the opening of the crotch-less panties. Karen said, "My dear family and friends, thank you for joining us today. I knew from the day I met him, that Jack was the man for me. I am honored that each of you joined with him in celebrating this event." While she was doing that, Nancy and Susie had placed their hands on my cock and balls, and were slowly jacking me off. Nancy slid a finger up my ass and also massaged my prostate. In seconds, with all eyes on me, I started to cum. Karen was holding the silver goblet that was full of cum from the 46 men I had recently serviced. I added my cum to the mixture as Susie milked me dry.

Karen handed me the cup and said out loud, "Jackie, to seal our marriage, I offer you this goblet. It is full of the best wishes of your peers, family and friends alike. Drink it down and in thus doing, seal your love for me." I looked at her. Last week, I would not have entertained the notion of sucking a man's cock, let alone swallowing the cum of 47 men. Yet, looking into her eyes, I knew I was in love. I took the goblet and drank deeply. Karen smiled and with tears of joy in her eyes leaned over and kissed me.

"I love you, Jack, now and forever."

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