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Showing posts with label cross-dressing. Show all posts
Showing posts with label cross-dressing. Show all posts

Friday

Halloween Costuming 1977, a Story

Halloween is my favorite holiday. I love to go “all-out for it.  My best friend, Linda knew this about me and took advantage of my enthusiasm by asking me to dress her up and do her make-up for a Halloween party she'd been invited to attend at her husband’s work.  I was glad she decided to be a Witch. (one of my favorite characters to enhance), cause I hate doing clowns.

On the agreed upon time, Linda and Bob showed up at my house carrying large plastic garbage bags of possible costume combinations.  “What’s going on?” I asked Linda.

“We brought a bunch of stuff ‘cause we didn't know what you would want to use for us.” She replied

“What do you mean, US?” I asked. “I thought I was just doing you!”

“Aw! C’mon!” she wheedled. “You know I can’t go to that party as the perfect Witch, if Bob goes in an average sort of get-up.  Besides, they have prizes for the best couple and we want to win!”

“No, No, No.” Bob piped in. “I don't want to impose. I can do my own make-up. you girls just do your thing.”

Linda started to object.

“Linda! I can do it myself.” Bob insisted good naturedly. And with that, he grabbed a plastic bag and went into the other room. So, I began painstakingly mixing iridescent green eyeshadow to a flesh toned make-up base and applied it to her face, neck arms and hands.  Tearing several black dresses to shreds, I hung them on her body. The ragged death-shroud fashion fit her perfectly. She began cackling hysterically as I finished her off. I could barely do my job, as I was giggling.

In the midst of our jolly mood, Bob entered wearing his costume.  My laughter increased to guffaws and my belly was in spasms.  He looked absolutely ridiculous! There was Bob, naturally built like a feather-weight, wearing a nurse’s uniform, cap and shoes carrying an old-fashioned metal bed pan and enema pack.

“You’ll make a better Witch than I!” Linda shrieked. Bob, at first laughed along with us. But, as the moments passed, he got red in the face, as I pointed out that he did not fill out his dress properly. He almost squirmed as I suggested that we enhance his beauty. But he consented to a make-up job.

Even though he had shaved earlier, pan-cake was the only thing that could cover his thick black whiskers.  We all grew quiet as I concentrated on heavily applying lipstick, rouge, mascara, and eyeliner. Pretty soon his face was transformed into a believable woman. Linda, sat staring at him, mesmerized. Once I was finished with his make up, I ran to my closet and pulled out an eight inch Auburn Afro Wig. It was a relic of the 70’s. I had thought I was so cool to wear that, then.  I  brushed it out to its complete fullness and carefully placed it on Bob’s head and accessorized his look with a pair of earrings.

Bob had no mirror to see what I was doing. So, when I was finished, Linda and I took him to the full length mirror in my hallway. For a brief moment, he looked like he was going to cry.

“Oh, my God!” he moaned. “I look exactly like my mother!” That had us in stitches another twenty minutes. Then, Linda and I were able to convince Bob to wear padded buttocks and bosom. I grabbed some small pillows from my sofa and squished them tightly into his bra. Er, I mean, my bra. When I told him to hike his skirt so I could stuff his panty-hose, he adamantly refused.

“I barely have a shred of dignity left!” He protested as he went into the bathroom to do it, himself. Linda and I looked at each other with raised eyebrows. Had we taken this thing too far? We decided to behave more respectfully.
“Otherwise, we won’t win!” Linda whispered. “He looks great! You did a good job” She patted me on the back. I smiled.

“I almost wish I could go with you.” I said.

Just then, Bob opened the bathroom door and stuck his head out. “How in God’s name do you women tolerate wearing this stuff? I am sweating like crazy!” He was about to wipe an arm across his forehead.

“Oh, No!” We both piped in at once. Linda grabbed a Kleenex and dabbed lightly at her husband.

“You don't want to smear it.” she admonished. Bob just rolled his perfectly done eyes, and sighed. His head was still sticking out from behind the bathroom door and the rest of him was hidden.

“What’s wrong, Bob?” I asked, fearful that he had changed his mind and I would have to do a clown costume and make-up instead.

“Uh. Well, I don't know how to make them line up with each other.” He said. Linda and I had all we could do to maintain straight faces. “Will you come in here and help me?” he asked his wife.

I was grateful as she went to his rescue. I gripped my belly as I bent over laughing. I could hear them tussling in the bathroom.

“Hold Still!” she said.

“It tickles!” he responded, giggling uncontrollably.

A few shrieks of laughter later, they came out of the bathroom with Bob’s bottom in proper position. It stuck out just fine! With his tiny waist, he made a very shapely nurse. Linda and I just stared at our creation with envy in our hearts, but silence on our lips.


The next day they came over to return my underwear and wig. They had won the contest for the best couple, a dinner out on the town in a fine restaurant. They joked continuously with me about all the fun I had missed. Apparently, a gentleman at the party found Bob quite attractive and followed him about like a puppy dog. Bob grew more and more uncomfortable with the situation.

“I want to tell you two something. I owe you both an apology.” Bob said. I couldn't imagine what he was talking about. “In the past, I have ridiculed you. But no more. I now know how it feels when guys look at you in a disrespectful way or hit on you. And from now on I will take it seriously if anyone ever bothers either of you, again.”
My mouth hung open in disbelief as Linda just knowingly nodded.

I have bruises on my pectorals and gluteals where guys grabbed at me last night” he said.
“But how could that be? You had all that padding” I said

"That’s just the point. Since they were squished up in such hard balls, over time they grabbed at me, it was like having a cannonball hit me.”

We sat in silence as we pondered this.

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Note: the pictures are only representative of Linda and Bob