Winning Strategy

Years ago, we lived in a rather small, tight-knit community. Half the town seemed to be related by blood. The townspeople were very ethnic and prided themselves on their Eastern European heritage. Parties, dancing, and lots of drinking are part of that heritage. Jean and I are social drinkers; we enjoy the light buzz alcohol provides us, but each of us rarely drinks to excess.In late September, we received an invitation to attend a costume party. We didnt know the couple very well who were hosting the party, but one of Jeans close friends did; her friend helped the hostess make up the guest list and it was through her efforts the hostess added us to the list. The costume party coincided with the weekend closest to Halloween. This particular party was well known for its excesses. People tended to lose all inhibitions and do things they would never do again, at least not sober and with a crowd egging them on. The people throwing the party took the costume theme very seriously and awarded cash prizes for best costume and best-costumed couple. There were two categories and winner took all in each category. Upon receiving the invitation, Jean not only immediately RSVPd, she also began plotting her strategy as she wanted us to take first place.Several days later, after much thought, Jean told me she had decided on our costumes; we were going to go dressed as Frankenstein and his bride. The twist was she was going to be Frankenstein and I was going to be her bride. We lived an hour from a large city. Jean got out the Yellow Pages and called all the costume stores inquiring if they had a Frankenstein mask and a bridal gown. One store did and she reserved them, arranging for us to pick up the costumes a week early. To our surprise the manager agreed to let us have the costumes a week early and not charge us extra.We went to the store to check them out. The Frankenstein mask was perfect. The clerk explained to us how his boss had acquired the mask from an actual movie set. The mask had a moveable jaw, a nose with actual nostrils that you could breathe through, and perforated ears so you could actually hear. The wedding dress was a costume piece, nowhere near as nice as a real wedding dress, but it was more than suitable for me to wear.

Jean wanted to make sure it fit so she had me try it on before we left the store. I had never worn a dress and felt more than a little self conscious being seen wearing it in a public setting (even if it were just Jean and the clerk who were going to see me). I went into the changing room and stripped down to my underwear and put the wedding gown on. Im small boned having narrow shoulders, slim hips, small hands and feet, and fine facial features. As I slipped the dress over my head, I had to admit I liked the materials texture against my skin. I walked out of the dressing room and Jean said, “Youre going to make a wonderful bride. I can already smell the money.” Jean had a brown wig in her hand. She handed it to me saying, “Put this on.” The wig was coarse and cheaply made. I put the wig on and looked in the mirror. The hair was long and came down past my shoulders. I asked Jean how I looked and she said, “Very pretty, we just need to get you some hose, shoes, and maybe some long lace gloves.”She asked the clerk if there was a veil and headpiece to go with the gown. He looked around and handed her a box. She opened it, took both pieces out and put them on me. The veil completely obscured whatever masculine features my face had making me really fit the part.Jean looked at me with a critical eye and said aloud, “Well get you fake nails and a makeup job. My friend Sue has some jellies we can use for your breasts.”

She looked closer at me lifting the veil and kissed me on the lips. “Hmmm, we may have to do something about your stubble as I want your face to be smooth. Well also have to pluck your eyebrows; they are too thick.”She looked at the clerk who was staring at me and said, “Well take it.” He looked at me and said, “Not meaning any disrespect, but your husband makes a pretty girl.” I felt myself blush. Jean said, “Thank you. I wish I had his peaches and cream complexion and with his figure, he can wear anything and look good in it.”I started to go and change but Jean said, “Leave it on. I want you to get used to it.” I looked at her seeking clarification. She said, “Thats right, just walk out to the car. Its no big deal. Youre not afraid of wearing a dress, are you?” I stammered, “No, its just a little strange.” The clerk observed us; his expression saying he didnt envy me. She told the clerk to include the wig. She paid the bill and we exited the store, Jean leading the way. She held the car door open for me and helped me get in. She got in the drivers side and we drove off. I was looking around thinking everyone must be staring at me thinking what a freak. Jean was quiet for a few minutes and asked, “How does it feel?” I said, “Very strange.” She said, “You really look good; were going to win, maybe both categories.” As we barreled down the interstate I became less self-conscious. Jean reassured me saying, “Theyre not looking at you because they see a guy dressed as a girl. Theyre looking at you because they see a bride. You really pass as a girl quite easy.” I said, “Thanks, thats just what I wanted to hear.” We pulled into town and now I felt really self-conscious. Jean said, “Dont worry I wont drive down Main Street.”

We took a side road and entered our neighborhood. We pulled in the driveway and as luck would have it our immediate neighbor was out washing his car. An older man, his mouth agape, he couldnt think of anything to say as Jean helped me out of the car. I rather hurried into the house and he returned to soaping down his vehicle. My luck had gone from bad to worse. All four kids were in the living room watching t.v., the oldest two looked at me as though I was the grossest thing they had ever encountered. I glared at them and whatever smart aleck comments they were going to utter, they kept to themselves. The two youngest thought I was the coolest and scampered out of the house in the direction of their friends house intent on telling them Dad is wearing a bridal gown and a wig. Jean caught them on the way out as I went into our bedroom.She brought them back inside and told all 4 why I was dressed in a bridal gown. She explained about the costume party and how we were going to win. She said they had to keep it a secret and made them take an oath. I was still in the gown looking at myself in the mirror when Jean joined me in the bedroom. She closed the door behind her and gave me a hug whispering, “That wasnt so bad, was it?” I told her, “It was worse than bad.” She said, “It will be all worth it when we take home the prize.” I had to admit she was right. Jean looked at my reflection in the mirror and said, “Youre quite attractive. Dont you feel sexy and a little bit kinky?” I admitted to her it was kind of erotic and I actually liked the feel of the material against me and the freedom of not having pants on was liberating. I said the wig is uncomfortable. I still had the veil on. Jean lifted it and kissed me. She whispered, “ill get a better wig and I think I want you to go without a veil, but were going to have to make your face baby bottom smooth.” It felt strange kissing her as she was wearing jeans and a sweat shirt. I felt like our roles had really flip-flopped. She ground herself against me and whispered in a seductive voice, “You really make a hot girl. You look good enough to eat.”

With that she pulled up the gown and dropped to her knees. I let the gown fall back down as I felt her yank my underwear down and take me into her mouth. I looked at myself in the mirror watching my expression as she fellated me. I thought to myself, “Not only do I look hot, but I feel like such a slut.” She was deep throating me and it felt marvelous. She had my buttocks in her hands as she guided me in and out of her mouth. I willed myself to keep my eyes open as I stared at my reflection in the mirror. She had just the head of my cock in her mouth when I felt my legs and chest tighten ass I ejaculated. Cumming while standing is a sensation all its own; its not difficult just different because its not an everyday occurrence. She kept me in her mouth until I became flaccid.She got out from under the gown and stood up, her lips were glossy. She grabbed my face with both hands and pressed her lips to mine, forcing her tongue into my mouth. I opened my mouth and she passed me my seed. I swallowed her gift of saliva and cum. She broke from the kiss and said, “That was hot, you came a lot.” I weakly smiled, not wanting to admit just how turned on I was. She said, “Go change and ill get dinner started.” No doubt I was getting off the hook from cooking for my bravery.I changed into a pair of sweat pants and t-shirt and helped her with dinner preparation. We ate dinner, the only topic the kids wanted to discuss was dad in a wedding gown and how freaky it looked. Jean reminded them of the party and their promise to keep it a secret. After dinner I cleaned up in the kitchen and the six of us played some board games. The kids then went into the family room to watch a video and Jean and I retired to the living room where we snuggled on the couch. She hinted a couple of glasses of wine would be nice and while I was at it to prepare us a snack tray. I opened a bottle of wine, poured two glasses and prepared a tray of sliced sausage and cheese, olives, and almonds and returned to the living room.Jean said she wanted to make a toast; we raised our glasses and she said, “To winning.” We clinked glasses and took a sip. We sat there listening to the stereo and talking about nothing important. She slowly steered the conversation back to the contest and how we had a lot of work ahead of us. I asked her what she was going to wear with the mask and she said she had already reserved a tuxedo.

She said, “This will be fun getting ready. Just promise me youll be a good sport.” I said, “Okay”, the pit of my stomach tightening in anticipation of what Jean had in store for me.The kids went to bed and Jean and I stayed in the living room. We had the room to ourselves and had a nice make-out session, warming us up for later behind closed doors.It was close to midnight when Jean whispered in a voice hoarse with desire, “Lets go to our room. I feel like ravishing you.”Motioning to the table, she said, “Leave it until tomorrow.” She took my hand and led me to the bedroom. In the bedroom, I started to undress. She walked into the bathroom where her nightgown hung and brought it out. She threw it at me saying, “Put this on.” Excitement was written all over her face. I started to say something, but obliged her. I was naked and I slipped the nightgown over my shoulders and let it fall. It was a deep purple in color. She watched me as she undressed, “Turn around.” I did. She said, “You look really good. Get on the bed and lay down.” Now naked, she climbed on the bed and got on top of me. She forced herself between my legs as we kissed. Her kisses were urgent, her tongue hot and very wet. She pulled my legs up and pressed her crotch against my bottom and she began to rub against me.

I loved the sensation and it brought back memories of years ago when she did this. I could feel myself hardening. I closed my eyes and imagined I was she and she was I. Jean had an almost frenzied look on Her face as she rubbed against me. I thought to myself shes going to orgasm. In between kisses she muttered obscenities and questions, “Does my baby like to be fucked? Come on, rub your cunt against my cock. I bet youd love a cock up your ass. Do you want me to find a cock to fuck you?” I played my new role telling her, “Yes, I love your cock. Fuck me. Yes, I want a cock up my ass.” Her rubbing against me simulating intercourse and the role-playing going along with it were wildly arousing. I felt myself approaching orgasm and told her I was going to cum. She ground harder her face reddened and her breath came out faster as she orgasmed. She thrust hard against me as I felt myself shoot my semen onto my belly.She collapsed on top of me. I held her tight to my body, my legs still clasped around her waist and my ankles locked together. I let out a sigh saying, “That was intense.” She said, “You can say that again.” So I did, and we both lay there laughing. My cum was all over her nightgown. I said, “Let me go clean up. Ill need to wash this tomorrow.” I finished in the bathroom and walked out naked to find her on her back legs spread wide. She said, “Go in my drawer and put another nightgown on. Then come over and eat me.” I opened the drawer and pulled out a long flowing nightgown, black in color. I put it on, loving the way it felt against my skin. Jeans eyes said it all. She was super turned on seeing me in her nightgown. She moved her body so her legs draped over the side of the bed. I knelt by the mattress and buried my face between her legs as she draped them over my back. I took my time eating her, savoring the texture of her flesh and the taste of her juices. From time to time I looked up; her eyes were closed and I knew she was locked in some fantasy while I tongued her. When her orgasm hit, she was strangely quiet and her eyes remained tightly closed. While eating her I felt my cock harden as it brushed against the smooth material of the nightgown. I imagined myself as a woman eating my lesbian lovers cunt. After Jean came, I half crouched and mounted her. Her cunt was sopping wet and I slid in. I pumped away imagining I was still a woman, but with a strap-on, fucking my lady love. Jean stroked her clit as I pumped in and out. We both came together, nice relaxing orgasms unlike the previous gut wrenchers.

As we cleaned up in the bathroom I asked her half in jest, “Can I get my pajamas on?” She said, “No, put on another of my nightgowns. I think ill sleep naked tonight. Well keep the door locked.” I exited the bathroom and fetched another nightgown out of the drawer. This one was short and deep red. I felt very exposed wearing this as it barely covered my buttocks. Jean walked out of the bathroom true to her word and completely out of the ordinary, naked. Jean has always been paranoid about having the kids walk in on us naked. No matter how tired she is, shell always put a nightgown on before going to sleep. We got in bed and she pulled me to her pulling my head to one of her breasts. I put the nipple in my mouth and gently sucked as she stroked my head. I would have given anything to know what was really going on in her head, to ascertain what deep seated emotion we had unlocked that day, but I knew it wasnt going to happen. Instead, I closed my eyes and drifted off to sleep suckling at her breast.I awoke early in the morning, refreshed and snug. Jean and I were on separate sides of the bed, her back was to me. I snuggled against her bottom and realized I needed to change. I got out of bed and after peeing changed into my pajamas and in vain tried to will myself back to sleep. I gave up, got up, put some coffee on and got the Sunday paper. As I read the paper, my thoughts drifted to the day before and all I could think of was, “What does Sunday and the rest of the week have in store for me?” can contact [email protected] OR [email protected]