My New Girlfriend has a Penis

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A lady and a transgender woman share a hotel room.
10.9k words
4.85
69.4k
200

Part 1 of the 2 part series

Updated 06/11/2023
Created 04/15/2022
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IsabellaEmily
IsabellaEmily
3,780 Followers

Greetings perverts.

This is a story I've long wanted to write, simply because I love the erotic imagery of someone discovering any sort of sexual pleasure or new attraction for the first time.

As with most things that I write this story takes place in a happy alternate reality where people don't worry about pandemics, std's, or the need for birth control.

Only two characters here, Emily and Alexa.

As always, I hope you enjoy reading about some of the things that arouse me in my fantasy life.

IsabellaEmily

~~

She was the most beautiful woman I'd ever been this close to in a sexual way.

And her cock was beautiful too, hanging between her legs as we stared at each other in the hotel room, anticipation, lust, and curiosity burning within each of us.

But first, let me back up a few hours.

~~

I like to explore new cities, but I hate the hassle that comes with traveling. Airport lines, baggage claims, delays, waiting for a taxi, the uncertainty of how clean a hotel room will be, and the gamble of hoping the airline doesn't lose your luggage.

Or ask any questions about the sex toys you've packed.

I was heading to a convention for SINEP, which is the company I work for, and I was looking forward to missing most of it.

No one that I knew was going to be there, so if I skipped seminars and sales pitches no one would be the wiser, and I'd have three days to myself, in what would hopefully be a nice hotel.

I don't get away from my husband and kids that often, and a chance to be out of town with no responsibilities was just what I needed.

I packed a new bikini in case the hotel had a pool. And in case it didn't I packed a slutty dress, which would help me introduce myself to someone young and handsome who might be willing to pump me full of hot cum.

I love my husband, but a few weekends a year I make it a point to get a rock-hard cock or two up inside me.

Shy college guys are my favorite, since they're grateful for the sexual attention, and they can usually get hard again almost immediately after cumming. Or stay hard.

I had my heart set on a young cock and had been wet on and off for days leading up to this trip anticipating the feeling of a stiff erection pushing into my tender hole. Young guys were not only fun to teach, but they were usually so excited to get laid that they didn't care if I was old enough to be their mother.

Yes indeed, if I could find some barely experienced twenty-year-old who could get nice and hard and stay that way all night I'd fly home a happy lady. and would be excited at the chance to get laid, even if I was old enough to be his mother.

And in case I couldn't find a guy who met my criteria I'd packed two vibrators and an anal plug so I could stay in and entertain myself.

The airline got me there almost on time, and they didn't lose my bag, although getting my rental car and finding the hotel in the sudden snowstorm that greeted me was a colossal pain in the ass.

And then there was the room reservation. Apparently, they had gotten my reservation through my company, but they'd gotten my city and state wrong, and booked me into a room on the top floor with a balcony shower and a hot tub.

Which thrilled me, until I got into the room and found someone in it already unpacking her clothes.

Once we made sure that we were each in the right room, we went down to the front desk to straighten it out.

And it turned out there was nothing that could be changed.

Every hotel and motel in town was booked full. And the hotel had assumed we were together because of the mis-labeled city on my reservation and had mistaken us for two women from the same city who wanted to share a room.

Fortunately my new roomie was as pissed off as I was about the situation. That made me feel less like a bitch for the complaining I was doing.

"Well, this fucking sucks." She declared, as we rode the elevator back up to the top floor. "I can't believe the whole city is booked."

She looked like she was twenty years old, but she had a convention itinerary with her reservation packet, so I assumed she was older than she looked.

"You're not wrong." I said, staring at the digital readout of the floors flashing by. "This truly does suck."

I was consumed with thoughts about all the orgasms and kinky fun I was going to miss out on.

I consoled myself with the knowledge that I looked pretty good for a forty-five-year-old mother and wouldn't have a hard time finding a married guy away from home who'd be happy to take me back to his hotel room and fuck me.

With a little bit of luck maybe I could find someone in their late twenties, although they mostly prefer women their own age. I might have to settle for a middle-aged guy.

At least middle-aged married guys were usually so grateful for a blowjob that they'd happily do anything that was asked of them.

"I'm sorry." Said my roommate. "I know it's not your fault, and I certainly didn't mean to imply that you're ruining my week."

I looked over at her and smiled, realizing that my irritated mood was probably making the young woman feel like a villain.

"I'm sorry as well." I said. "I do feel like my week has been ruined, but I hope you don't think I'm blaming you. It's the fucking hotel that screwed us."

She smiled back at me.

"At least we're on the same page." She stuck out her hand. "My name is Alexa. Alexandria really, but you can call me Alexa."

"I'm Emily." I told her, taking her hand. "Is this your first convention for SINEP?"

"Yes, it is." Alexa replied. "I've only been with the company for a few months. No one else wanted to go, so I was told to volunteer."

"Our office is the same way." I laughed. "Except I usually like coming. No one keeps track of what I do while I'm here, and I have the whole time to myself on their dime."

The elevator doors opened, and we stepped out into the hallway and headed for our suite.

"I was looking forward to that part." She said. "Having some time to myself. I was going to explore the city before I realized we'd be snowed in. I was going to meet people. I was going to enjoy myself. How were you going to spend your time?"

I opened our door and lead the way into the room.

"I was going to get laid." I grinned. "At least that was the plan."

She stood looking at me for a moment, probably unsure if she heard me right.

"You heard me right." I laughed. "I was going to find some young stud and let him fuck my brains out."

She grinned.

"At least I'm not stuck with someone boring." She said. "But I am sorry that you're stuck with me. If you need some privacy let me know and I'll take my laptop and go sit in the lobby."

"I appreciate that." I said. "But I couldn't do that to you. I wasn't interested in a quick date, I wanted hours and hours of sex. The kind where you fall asleep wet and wake up sticky and start again."

"I guess that does sound better than the convention." She said.

"You guess?" I asked. "I know we just met, but Alexa please take my word for it, a hard cock and some orgasms are way better than anything the convention will offer."

"Oh I believe that." She said. "I just haven't had a lot of real-life experience in proving that to be true."

"I'm sorry." I said, seeing the worried look on her face. "I didn't mean to bring up something that would make you uncomfortable."

"It's okay." She said with a smile. "You weren't being mean. Just honest. Sorry you're stuck with me instead of able to have a good time."

She went to the window and looked down at the snowy city below us.

"It's not your fault we're stuck together." I said. "And from the looks of the weather my plans might not have worked out anyway, even if I had the room to myself."

"I heard the guy downstairs say we might be snowed in by later tonight." She said, turning from the window. "For better or worse we really will be stuck together."

I felt bad. My plans might have been ruined, but it certainly hadn't been Alexa's fault.

And I realized I was behaving exactly like the stuck-up older women I'd hated when I was her age. If I didn't do something to make it up to her, I was going to hate myself for it.

"Then we might as well make the best of things." I said, forcing some cheer into my voice. "Let's shower, change, and head down to the bar for some drinks and some food. Afterwards we'll get some junk food and maybe find a movie to watch on the pay-per-view."

"That does sound nice." Said Alexa. "I could use something to eat."

"Me too." I said. "And drink. You can shower first and I'll unpack some of my things."

Alexa stared at the shower.

As advertised, it was on the far wall of the room, and technically it took up a third of the balcony. Three sides of the shower were clear glass, enabling a clear vision from the shower into the room, onto the balcony, and out at the city below.

The floor, the ceiling and fourth wall were tiled to look like a dark stained wood, giving it the feel of a sauna.

The wall of the shower that looked out over the city was tinted green, indicating that it was the kind of glass that allowed whoever was inside to see out, without anyone outside being able to see in.

Not that anyone would be up this high. At this height you could probably stand on the balcony and scream at the top of your lungs and no one on the sidewalk would even notice you.

"Is there a shower curtain?" Alexa asked.

"I don't think there is." I said, walking up to the shower and looking around. "I suspect this room is usually occupied by couples who like watching each other shower. I guess the only real privacy is in the bathroom."

The room had a hot tub outside on the balcony as an added feature, not that it did us any good in a blizzard. And in the corner of the room was a small bathroom, with a toilet, and double sink.

"Oh." She said, her face reddening.

I instantly realized that she was embarrassed. While showering in front of strangers hadn't bothered me for years, I remembered being at an age where it did.

"If you like I'll shower first, and then I can head downstairs, and you can join me after you're done." I said. "Or I can sit and watch tv and I promise not to look."

"You probably think I'm strange." She said softly.

"Alexa we've already established that I'm the strange one here." I said. "You don't need to be embarrassed if you'd like a bit of privacy."

"Well," she said slowly, "it's sort of a weird thing, but I hadn't planned on having to tell you or even mention it, but I didn't realize that the shower was so.....open like that."

"I'm sure there's nothing you can tell that I'll think of as weird." I told her. "I've been showering in front of other women since college, and I doubt you have anything that all those other women I've seen didn't have."

"Okay." She said. "I guess there's something I need to tell you, because the sooner you know, the sooner we can figure out how we're going to deal with it."

"You weren't sent here by my husband to keep me from getting laid were you?" I teased.

She flashed a quick smile, and I realized that whatever was on her mind was serious.

"Hey I was just kidding." I said. "Unless you're a serial killer I'm sure we can figure out whatever it is you're worried about."

"Maybe we should sit down." She said.

"Sure." I said. "But in case this is as serious as you say I'm getting something from the mini-bar."

I opened the compact fridge and spotted some wine-coolers. I took out two of them and handed one to her.

"You look like you could use one too." I said, sitting down.

She took the bottle and stared at it for a moment.

"You are old enough to drink, aren't you?" I asked, raising one eyebrow.

Even though my boss didn't care what I did at the convention, I'm sure she'd be pissed if I got an intern drunk.

"I'm twenty-five." Laughed Alexa. "You won't get in trouble for giving me booze."

"That's a relief." I said, twisting the cap off the bottle.

"First off," she said, taking a deep breath, "I should say that if you want me out of the room, I'll get my stuff and leave. Or if you want to leave, I'll pay for another room for you anywhere you can find one."

She was looking at the floor and still holding her unopened wine cooler.

"I don't tell strangers this." Said Alexa. "And I wouldn't be telling you, but with the shower, and there only being one bed in here, it would be unfair not to tell you."

"Whatever it is," I said, "just go for it."

"I'm a female." She said. "And I have a penis. I've always felt like a female, and for six years now that's the way I've lived."

She paused and took another deep breath before continuing.

"But I have a penis and if you're going to be forced to be in a room with me you're going to find out, and I'd rather have you know now than find out by seeing it and being weirded out or offended."

"Wow." I said. "That is not what I was expecting."

"I've never told a stranger before," she said with a shy smile, "but I don't think there's an easy way to say something like that."

"I think you said it just fine." I told her. "It's not something I have a problem with, but I am glad that you told me. I appreciate your not wanting to surprise me with it, and I really respect your courage in telling me."

"I wasn't sure I should." She said. "I thought maybe I'd just change in the bathroom and wear lots of layers to bed and you'd never see it. But that shower. Sooner or later, you'd see me. Especially if we're trapped here for several days."

"Well, it would have surprised me." I admitted. "I would have never guessed. If you hadn't said anything I might have never even known."

"Yeah but the longer I kept it hidden the worse, it would seem if you did." She said.

"No. Not worse" I assured her "It would have been more of a surprise for sure, but I'm a fan of penises, so I promise I wouldn't have been mean about it. Surprised maybe, but not mean."

"I appreciate that." She said. "I feel a lot better. I was afraid you'd be angry."

"I will be as respectful of your privacy as I can in these cramped quarters." I assured her.

"Thank you." She said. "You act towards me however you're most comfortable. But I am a female and you don't need to keep your distance on my account. I'm comfortable around women and I'm just like you. Except for my genitals."

"Well, you need to be forewarned." I told her. "If you catch me looking it's just curiosity. Please forgive me in advance for that, because I'd never want to make you feel like a freak."

"Oh I am a bit of a freak." She said. "Not too many women have a working penis. I'm certainly unique in the small town that I'm from."

"Well I think you're unique because you're beautiful, friendly, and have an amount of courage and confidence that I didn't have when I was your age." I told her. "This might not be our first choice, but I am glad I'm getting to know you."

"Really?" she asked.

"Really." I replied. "Now we should get cleaned up and get on with finding some dinner."

"I guess I'll shower then." She said. "As long as you won't mind?"

"I won't." I told her. "I promise. I'll hang a few things up, turn on the weather channel, and I won't peek any more than twelve or fifteen times."

She laughed.

"Peek all you want." She said. "I sort of like to be watched."

My eyebrows went up.

She blushed.

"I'm sorry." She said. "I wasn't trying to be weird. I do like to be watched in a sexual way, but I won't mind if you peek. And if you do look, I won't think that it's a sexual thing."

She stood up and went towards the closet, before turning around.

"In fact," she said, "if you're curious I'll show myself to you. You don't have to look, but if you want to see I don't mind. Like I said I won't consider you being curious a sexual thing."

"Well I am curious." I admitted. "But I don't want you to be uncomfortable. I was pretty much teasing about peeking at you. But if you'd like to show me I would very much like to see you."

She pulled her blouse over her head and tossed it towards her open and empty suitcase, and then reached behind herself and unhooked her bra.

Her breasts, tiny and firm with gorgeous little brown nipples came into view and I tried not to stare at them.

I've never done anything sexual with another woman but have long been very aware of my visual attraction to small and perky breasts.

She saw me looking and smiled, and I realized that she truly didn't mind being watched. She wasn't showing off, and she wasn't being provocative, but she wasn't embarrassed or uncomfortable either.

She unsnapped her knee length skirt and let it fall around her feet, and then kicked it towards her suitcase.

She turned back towards me, and just as she had said, in her pretty pink panties, was a definite bulge.

A strange feeling shot through me, and I realized that I found it incredibly erotic to see a beautiful female body standing in front of me, with such an obvious penis in her panties.

Alexa put her thumbs in the waistband of her panties and pushed them down, bending to pull them off her feet one at a time, and then threw them into the suitcase as well.

When she stood up, she took a step towards me, and I saw that her penis was completely hairless. She had a tiny tuft of blonde pubic hair right above the cock, but her penis and balls looked completely soft and smooth.

Her soft penis was less than three inches long, and it looked fairly thin. I couldn't help but notice that it fit the size of her body so perfectly and looked positively gorgeous.

"You're a beautiful woman." I said, hoping I didn't sound as stupid as I was afraid I did. "Beautiful all over. In every way."

"Thank you Emily." She said softly.

She turned and picked up a bottle of shampoo, and then opened the door to the shower and stepped in and turned the knob.

She jumped as a burst of what was probably cold water hit her, but I quickly saw steam start to rise, and she put her head into the water, and I wrenched my eyes away, unsure that I'd be able to stop looking if I watched for any longer.

Because the truth was that I wanted to watch.

I wanted to press up against the glass and stare at her.

It seemed crazy to me, that I was feeling so drawn to someone I'd just met. And not just someone, but someone that was a female.

Was it the lone male part of her that I was drawn to?

Or the feminine beauty that had captured my imagination?

Or the gorgeous juxtaposition of her female body with the absolutely male cock?

Was I physically attracted to her?

Or was it her courage and confidence and vulnerability that had pulled me in?

If I was physically attracted to her, was that fair? Would I just be treating her as a sexual prop?

I realized that I was standing still as I wondered all of this, and I moved to my suitcase and started to hang up my things, and then I unpacked the rest into the empty drawers of the dresser, leaving out a sensible skirt and blouse for dinner.

I was tempted to dress as sexy as possible for dinner to impress Alexa, but I wasn't sure why I felt that need. I put that thought out of my head and started to get undressed for my own shower, stealing a glance to see if she was almost done.

She wasn't.

She was washing her cock and balls, her fingers moving slowly and gently as she worked a soapy lather around them.

I felt myself tense up as I watched and felt my heart thud in my chest. She was standing with me on her right side, and she was facing left, staring out the glass wall of the shower at the city below.

I watched her hands working and then I again wrenched myself away. If she caught me staring, she'd think I was a complete pervert. I turned the television on and sat down to search for the weather channel in my bra and panties.

I was determined not to look into that shower again until Alexa was out of it.

IsabellaEmily
IsabellaEmily
3,780 Followers