Becoming Elizabeth Ch. 02

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Testing the waters.
3.1k words
4.5
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Part 2 of the 5 part series

Updated 10/29/2022
Created 12/22/2010
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Author's note: Some of the sexual behavior chronicled here is patently unsafe. I really hope that the story makes your dick hard (or pussy wet, for my gentle female readers), but use some sanity when you're out in real life.

As usual, there's truth mixed with fiction, but mostly fiction. I'll let you decide what's real and what's not.

Chapter 2: Testing the Waters

Debby and I left for Rockport on Friday morning. It wasn't that far of a drive, and we arrived before noon. After getting everything set up, we went through an underground newspaper that she'd picked up at an adult bookstore near her work. I was surprised to find out that Corpus had three gay bars listed. It's not really that large of a town, and I didn't expect more than one.

Late in the afternoon, we headed down to Corpus and had dinner. We were both anxious about getting to one of the bars, so we sort of hurried through it. It was early evening when we pulled into the parking lot of the bar that she thought we'd have the best chance at.

It was a disaster. Neither of us were into the bar scene, so we were bit uncomfortable to begin with. The crowd was early 20's, and even I stuck out like a sore thumb in my early 30's. Plus, the music volume was mind-splitting and we had to yell to each other to be understood. We endured about a half hour of being ignored, even by the bartender, and left.

Getting back in the car, Debby directed me to the second of the bars listed. It was more our speed, fairly quiet with an older clientele. However, it didn't pan out much, either. The second bar turned out to cater more towards transvestites and transsexuals. While a few guys came on to Debby, they were surprised to find out that she was a real girl and even more surprised that she was there with her husband. They weren't interested in me, and I wasn't interested in the men dressed as women.

Depressed, we called it a night and went back to Rockport. Debby was in a grumpy mood on the ride back.

She was so perturbed that we didn't even fuck that night. I tried to cheer her up, to no avail, and we finally went to bed.

As we lay in the darkness, I heard her say quietly, "Do you trust me?"

"Implicitly," I replied.

"Do you love me?" she asked.

"Madly," I said.

"Remember that tomorrow," she said, rolling over away from me and going to sleep.

She was in a much better mood in the morning. She didn't wake me up with a blowjob, but she wasn't as grumpy as the night before. She announced that we were going shopping.

I had hoped to do a little sight-seeing while we were there. While we'd come to Rockport a time or two since we married, we didn't go into Corpus that much. I wanted to see the aquarium and the aircraft carrier, but she once she decided that we were going shopping, all those plans were tossed out the window.

Shopping with her is an ordeal. I love her, but I want to run screaming when she asks me to go with her to a department store or a mall. It always turns out the same: I push the cart, she shops. She'll hold up an article of clothing or something, and ask my opinion of it. I always say the same thing: "Looks great, put it in the cart." She's learned to ignore that, yet she still insists on asking my opinion.

We drove back into Corpus, and stopped at the first department store we found. Her usual route was purses, shoes, clothes, housewares, and then electronics. The last part was pretty much an apology to me for having drug me thru the rest of it.

She surprised me this time by heading straight to the womens department, then surprised me further by walking right past the plus sized area (she's not huge, but as I mentioned before, she is overweight). I followed her, pushing the cart.

We stopped at bra's first. She glanced at me with a critical eye, then picked up several lacy ones and tossed them in the cart. Panties were next. Then, on to dresses.

She picked several slinky dresses off the rack, then motioned me over. She held one, then another, than another up against me.

"What are you doing?" I hissed at her. Honestly, I had no clue.

"I thought you trusted me," she asked in an innocent voice.

"I do," I said, "but..."

She interrupted me. "No 'buts'. If you trust me, then do what I say and push the cart." She leaned over and gave me a peck of a kiss on my cheek.

The most embarrassing part was shoes. She blithely picked out several styles, and had me try them on right there in the store. I almost refused, but she gave me a stern look. The last thing I wanted was for her to get in a bad mood again, so I complied.

We trundled the cart to a register, paid, and left. After a quick lunch at a fast food restaurant, we headed back to the beach house. Once there, she told me what she was doing.

"You didn't seem interesting to anybody last night," she explained. "Especially at that second bar. So, I'm going to make you more appealing and we're going back there tonight."

We unloaded the bags, and then she led me to the bathroom. She started the shower, and we both undressed and stepped inside. As the steam fogged the mirrors, she washed me. We seldom fucked in the shower, so all this attention got my dick hard.

"Hmmm," she said, looking at my dick sway back and forth. "We need to take care of this."

She dropped to her knees, and quickly wrapped her lips around my dick. She proceeded to give me a totally utilitarian blowjob, designed to get me off as quickly as possible. It didn't stop me from enjoying it, though. The only part I didn't like was when she stood up, pressed her lips against mine, and pushed my cum into my mouth.

"Swallow it, baby," she said. Grudgingly, I complied.

My dick, sated, went back to sleep. Standing up, she grabbed the shaving cream and razor. I stepped back away from her.

"Whoa!" I said, holding my hands up in front of me. "Where do you think you're going with that?"

She put the hand holding the razor on her hip. "Listen, missy," she said, "just shut up and let me finish, ok?"

"Missy?" I asked, breaking into a grin. It sounded funny.

"Yep, once I get done with you. Now get over here," she said sternly, filling her hand with shaving cream.

She shaved my entire body...and I mean entire. Legs, chest, crotch, armpits, even the little patch of thin hair I had on the small of my back. Then, she handed the razor to me and told me to get rid of the mustache.

That was difficult. I'd had a mustache since I started shaving. It was a dear friend of mine, and I thought it looked good on me. Debby, however, thought it made me look evil. Slowly, regretfully, I shaved it off. My upper lip felt naked.

She turned off the shower, stepped out, and dried me off. Then, she led me to the bedroom and started opening the bags from the department store. The first thing in her hand was the panties. She stared critically at my dick for a second, then looked up at me.

"I have NO idea what to do about that," she said. "You'd just better not get turned on tonight." I stepped into the panties, and my dick twiched in rebuttal to her warning. I willed it back down.

Next was the bra. It was an A-cup, but she'd bought padded ones to give me something more of a female form. Then the nylons. Last was a blue semi-slinky dress. She'd judged all my sizes correctly.

She told me to close my eyes, and led me back to the bathroom. "Don't peek till I'm done," she warned. I was tempted to, but she was having a blast being in charge and I wanted her to enjoy it.

She turned me around, away from the mirror and pulled out her makeup bag. She trimmed my eyebrows, then proceeded to apply a foundation to my face, followed by lipstick, eyeliner, and mascara. She did her best with my hair...I had longish hair for a guy, but not long enough that she could do any styling to it. She ended up brushing it straight back.

She laughed and said, "You look like a dyke with that hair." I started to turn around and see what she meant, but she stopped me.

She finally finished and said, "Ok...turn around."

I turned around and was shocked. I barely recognized myself. I was never very buff or muscular, and had something of a slight frame. At a glance, I could easily pass for a woman. And I was attractive, too! If I saw my reflection in a bar, I wouldn't avoid her. "Holy shit," I said.

Debbie put her arm around me and looked at our reflections. "You should have been born a girl," she laughed.

I reached out and grabbed one of her tits. "I don't think so," I said, giving it a good solid squeeze.

She put some perfume on her, then me. Putting my wallet in her purse, she led me the living room, then stopped.

"We have to do something about your walk, too," she said, a concerned look on her face.

I have what Debby calls a "John Wayne" walk. There's a bit of swagger in my giddyup, so to speak. It took quite a bit of time and effort on both our parts to get my walk down to something even remotely feminine.

"Remember, short steps!" Debby said, cheering me when I finally got it down.

She picked up her purse and grabbed the car keys. As we walked towards the door, I had something of a panic attack. All this was fun inside, but I was having second thoughts about going out dressed like a woman. I hesitated.

Debby stopped and gave me an inquisitive look.

"I'm not sure I can step out that door," I said, honestly. I actually grabbed the back of the couch, like the house would suddenly tilt and spit me out the front door unprepared. My knees wobbled a little bit.

Debby walked up to me and hugged me. "You look fine," she said. "Besides, what's the reason we're doing all of this?"

I mumbled, "So I can see you with another girl."

"Right," she said, patting my shoulder. "So, no outside, no pussy for me to lick."

I debated for a minute. At first, I thought that giving that up might be a fair trade to stay inside. But, all this WAS fun, and Debby was having a grand time. It was kind of exciting, also.

I shook my head. "Ok, let's go," I said, reaching for the car keys.

Debby danced away from me. "Oh, no, I'm driving," she said. I always drove, but she was taking every bit of masculinity out of me for tonight.

As we drove to Corpus, she suddenly said "You need a name, a girls name. What do you think?"

I thought for a half-second and said, "Jackie?"

She shook her head. "Too tomboyish," she replied. "Try again."

"Elizabeth?" I ventured. It was her middle name.

"I like that," she said. "I'm Deborah Elizabeth, and you can be Elizabeth Deborah. Nice to meet you, Liz."

"Nice to meet you too, ma'am," I said in what I thought was a girlish voice.

Debby gave me a disappointed look. "We'll need to work on your voice, too, but that'll have to be another time."

We arrived at the bar, and the difference from the night before was like night and day. Rather than being fairly ignored, heads turned and I heard snippets of conversation about us float by..."...new girls...."

We walked up to the bar and sat down. I ordered a bourbon and coke, but Debby countermanded that with a daiquiri.

"Hands in your lap, Elizabeth," Debby whispered to me.

It didn't take long for the first adventuresome soul to walk up to us. He was in his 50's, balding, but looked like he was in good shape.

"HeLLO ladies," he said. "My night just got better now that you two hotties are here."

Debby rolled her eyes and gave me a quick "no" shake of her head. We talked with him for a few minutes, pleasantly but noncommittally, until he finally got the hint and wandered off.

Having experienced my first pass, I mentally apologized to all the women in bars that I had used similar lines on. Did I look as ridiculous back then as he did now?

We'd finished our first drink and was on our second when another man came up. Younger than the first, but not in as good a shape. He walked up to me and extended his hand, but turned to Debby when he said, "May I have this dance?"

Debby smiled and nodded, then looked at me. I gulped, nodded, and let him lead me to the dance floor.

The DJ was playing a slow song, and he put his arms on my hips. I had no clue what I was supposed to do, but a quick glance around the dance floor gave me one. Copying the other "girls" on the dance floor, we began dancing. I was stiff and uncomfortable.

He pulled me closer to him. "Nice lady," he said. "Your mistress?"

I shook my head. "Wife," I replied.

He chuckled. "Actually, I was thinking more of the slave/mistress kind of mistress," he said, smiling.

I grinned at him. "Isn't that pretty much the same thing?"

He threw his head back and laughed. "Touche," he said

We talked as we danced, and I was pleasantly surprised that I was moving more gracefully and less stiff. It helped that his hands had slipped off my hips and around to cup my ass.

As the song was ending, he pulled me close against his body. I could feel his hard cock press against me.

He whispered in my ear, "Do I need to ask her permission to go any further with you?"

That was an excellent idea, and I'm glad he assumed he needed to. Debby would probably have a better judgment of men than I would. I quickly nodded.

He led me back to the bar. I sat down and took a sip of my drink ("Little sips," Debby kept telling me) while he leaned over and said something in Debby's ear. I couldn't hear what he said, but it evidently pleased her. They exchanged whispers back and forth for a moment, then he smiled at me and walked off.

I leaned over and asked her, "What was all that about."

She smiled at me and said, "I just set up your first date for the night."

"Oh," I said, my heart beating a little faster. I don't now if it was from fear or excitement. We sat for a few minutes, then Debby got up and said, "Come on, go with me to the bathroom."

I stood up and followed her. I almost walked in to the mens room, but was saved at the last second by Debby's quick yank on my arm.

She towed me into a stall, then held the door open a bit behind us.

"I know you girls go to the bathroom together, but I didn't realize how much 'together' it was," I wisecracked.

"Hush," she said. "Sit down on the toilet. You don't need to pull your dress up." A second later, the door to the stall opened and my dancer friend slipped into the stall with us. It was crowded with me on the toilet, Debby standing next to me, and him standing in front of me.

"Go ahead, Elizabeth," she commanded, "suck his dick."

He quickly unzipped his pants and pulled his hard cock out. I leaned forward as his hand went to the back of my head, and his cock slipped between my lips.

In that instant, my mind flashed back to my teenage years when I sucked Scott's cock. He had said that I did a good job sucking him, and I did everything I remembered from that time now.

My mouth slid up and down his cock, and I pulled back and gave special attention to his cockhead. He made soft appreciative noises, urging my head forward to take his whole shaft again.

He got a little carried away and pushed his cock too deep in my mouth. I gagged.

"Sorry," he mumbled, pulling back a fraction of an inch. I regained my composure.

I glanced up at Debby at one point. I could tell she was horribly turned on. One had was shoved between her legs while the other one squeeze her breast. The man who's dick I was sucking had her other breast in free hand.

I sucked noisily, wetly. I didn't know if I was actually doing a good job or not, but he seemed to be enjoying it. Dimly, I heard Debby's breath explode out of her as she orgasmed.

I was really sucking him hard and his hand was urging me faster and faster when suddenly he reared his head back and made a noise that sounded like "Nnnggg". Instantly, my mouth started filling up with his tangy cum. It actually felt like it was burning my tongue and lips.

Coached by Debby, I swallowed as much as I could, but some still slipped out of my mouth and left cum droplets on my dress. I kept sucking and swallowing until he pulled his dick out of my mouth.

"Thank you, babydoll," he said, patting me on my head. He turned to Debby. "And thank you, ma'am," he smiled at her. He poked his head out of the stall, glanced around to make sure nobody was there, then left.

I wiped as much of the cum off my dress as I could. then followed Debby out of the bathroom.

"Enough for one night?" she asked me.

I nodded. We paid our tab and walked out to the car.

As I was getting in the car, I saw cum stains on the dress. "Shit," I complained. "Will this come out of my dress?"

Daisy laughed at me. "You're more a girl than you let on," she chuckled.

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5 Comments
BrendaNWBrendaNWover 4 years ago
very hot

I think that both of them are going to have a wonderful time expanding their lives

cdCindy1cdCindy1over 6 years ago
my fantasy exactly

I would love for my wife to set up a man for me to suck his dick -- especially with her watching. I love crossdressing and fantasize all the time about my wife helping me dress and especially helping me with my make-up. I haven't yet told her that I'm a sissy faggot CD cocksucker -- maybe one day i will.

AnonymousAnonymousover 7 years ago
my wife too

I fantasize all the time about my wife doing this as well. Watching me suck a dick in front of her with the guy fondling her tits and making out with her. That would turn me on. I truly want to be a sissy cuckhold faggot cocksucking bitch. I can't wait to read what happens next in your story.

Tootight1Tootight1almost 9 years ago
loved it

I've had similar times, with wife, and were great.

TammiBadgerTammiBadgerover 13 years ago
Nice Beginning

I hope these two have many more adventures ut of town and even more when they get home.

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