Jake/Ashlyn--Magic Boobs 2

Okay, I’ll have to continue my “Thanksgiving recap” tomorrow. I wanted to mention a few things that happened last night.

Cambridge is an interesting place. If I was really an attractive single young woman, this might be the perfect place to live. The area is teeming with young singles because of the numerous colleges. Cambridge is also the home to MIT and Harvard. You can almost smell the intelligence in the air. This creates and interesting dynamic that I think affects the people and businesses of Cambridge.

Which brings me to where I work.

It’s an eclectic place. It’s part cocktail lounge and part “mom and pops dinner”. You can get a killer drink and a blue plate special all at the same time. The wait staff is hip and sexy. I struggle with the hip part because I’m really over a decade older than I look—but I make up with the sexy part. I learned early on showing a bit of cleavage and sexy stride got me better tips.

The original Ashlyn was a party girl—and she knew a lot of people. On a fairly often basis, customers of the lounge come running up to me and give me a hug. They give me the old “Wow, where have you been?” or “Are you going to this party or that party?” I’ve gotten pretty adept at pretending I recognize everyone.

Which brings me to table 1 in the private dining room, party of four.

For a Tuesday night we were “in the weeds” which is restaurant slang for being really busy. I was in a funky mood when I had gotten dressed for work, so I probably pushed the sexy thing a little far—short, short skirt and a top that looked painted on. So when I walked up to my “party of four” and it turned out to be a table of middle-aged guys, I new I was going to well in the tips department.

I give them a big smile. “So what can I get you boys this evening?”

“Hello babe.” One of the four acted like he knew me. He had Italian features and his suit looked high dollar.

I hesitated, unsure if I was reading him correctly.

“You don’t remember me!” He feigned being hurt, “How could you forget me? It’s me, Anthony… you danced naked for me during your audition.”

I blushed all the way to my toes, but the little pieces of info clicked into place for me. Right after I decided to live Ashlyn’s life and caught a train to Cambridge, the first thing I did was check the messages on her/my phone. There was a message from an Anthony who ran a strip club—he was disappointed I had decided to turn the job down.

“Anthony! Sorry, it’s kind of dark in here. I didn’t recognize you.” I wasn’t sure how well Ashlyn new this guy, so I leaned over and gave him a hug. I’ve found guys never turn down a hug from a girl as stacked as me.

“So this is what you are doing instead of dancing? What a waste of your talents.” He turns to his companions. “This is the redhead I was telling you about. You should see her tits, they are world class.”

One of the other gentlemen pipes up. “You have any work done?”

The question kind of caught me off guard. It was a rude question, but the guy was so straight forward I could tell he wasn’t trying to be offensive. I really didn’t know, but I didn’t think so, so I told him no.

“Amazing.” He says.

“What I tell you!” Anthony tells his companions.

I took their drink orders, and ran off.

They ended up staying for a couple of hours. I ended up spending a lot of time at their table. At one point they demanded I sit and have a drink with them. Since it was the private dining room I didn’t see the harm. We sit, drink and tell dirty jokes. It was actually kind of fun.

Finally they decide it was time to leave. I present the bill and Anthony pulls out an envelope. From the envelope he pulls out a gift certificate. I see the amount on the certificate.

“Wow. What a nice gift! Someone must really like you. I’ll go get your change.”

“Nah, you keep the change.” He motions for me to come closer. “Actually the gift certificate was an anonymous gift. It just showed up in the mail.”

“Lucky you.” I say.

“No, lucky you.” He replies back.

He pulls out a huge roll of cash. He takes two one hundred dollar bills off the top and shows them to me.

“Come closer.” He says to me.

I get right up next to him.

“Lean down.”

I hesitate, uncertain as to what he was doing—but he had been kind to me all evening, so I decide to trust him.

He looks me in the eyes. “I know why you turned down the job, and I understand. What you don’t know is I run a classy joint—and what you did for us this evening, taking care of four businessmen, making conversation and sharing a drink isn’t all that different from what my girls do at the club.” He pauses. “They just do it with less clothing.”

He folds the bills and slides them down into my cleavage.

“Thank you.” I awkwardly say to him.

I turn to leave.

“How would like to double that two hundred?” He says to me.

“Excuse me?” I was surprised.

“I’d like my business associates to see those world class tits of yours. Take off your top and I’ll tack on another two hundred to the tip.”

A million thoughts entered my head at that moment.
And I was conflicted.

I’ve enjoyed dressing up in short skirts and tight low tops, flaunting my borrowed good looks. It’s like I’ve been in costume in a play, and I have been having fun with the part.
Up to this point it’s been all harmless and fun.

The way these guys were looking at me—this was different. If I did what he asked I would be crossing some kind of line.

The money could help cover my trip to Texas. If I did this, what kind of girl does that make me? And does it matter? I may not be in this body in six months.

I was repulsed, yet intrigued that I could make so much money just for flashing my boobs at these guys.

“Right now? Here? Someone could walk in.” Maybe I was looking for a way to say no without saying it.

“I’ll add another hundred on for the risk.” He took off three one hundred dollar bills off his roll of cash.

“Deal.” I couldn’t believe I said it. My stomach felt sick and my heart started to race.

I reached for my top and I started to quickly pull it off—I had a band aid mentality, do it quickly and get it over with.

“Whoa! Slow down and take it easy. Go nice and slow, let us enjoy it. Give us a show.”

So I take my time. I remove my top and stand there for a moment in my bra. I had worn one of my sexier ones. I reach behind and undo the clasp of my bra. I turn away from the men and totally remove it. I turn back and face them—topless.

I let them get a good look—they paid for it.

The men made all sorts of appreciative noises. “Those are some fine looking tits.” One of them announced.

I walked over to Anthony with my hand out. He reached into his pocket and pulled out a business card and handed it to me along with the three hundred dollars.

“You could make this kind of money every night.” He says to me. “I have a soft spot for red heads Ash, you still have a job if you want it.”

I get dressed. They watch.

Once I’m fully dressed everyone is pleasant again. It’s like it never happened; only I’m 500 + richer.

I know I should be disgusted with myself—but I keep thinking “Those idiots just paid three hundred dollars to see my boobs.”

I walked the gentlemen to the door, wish them a good night, and go back to pick up the check and gift certificate. When I get it, I look at the price again—It more than covered the bill.

There was also some writing on it.

It said: Be sure to ask for Ashlyn. I’m a big fan of hers. From a secret admirer.

I froze when I read it. Anthony probably assumed that the secret admirer was for him—but it doesn’t say “from YOUR secret admirer”. It says “from A secret admirer.

My intuition was telling me that maybe this was my admirer.

I’m not sure what to think. I probably ought to have lunch with Art and run this by him. We’ve got things to talk about anyway. I need to pick on him for sleeping with a dude, and I’m sure he needs to do the same to me for showing my boobs for money.