Several weeks after I met Roxy, I began to feel slightly more comfortable with being with a transsexual. By that I mean I was willing to go out of the apartment at night in a safe area that was poorly lit. Roxy was a good sport, she was so relaxed and at ease, it rubbed off on me. I had met her roommate Dianna by now and we got along like old friends. Dianna was more obviously transsexual but she did dress very sexy and was a wiz with makeup. I knew she was a man but in a club at night I think she would be able to lead most men home by the member, if you take my meaning.
Roxy and I decided to go out and eat; we drifted down to Broadway and eventually had a couple slices of pizza at Rizzoli's. We had a beer with dinner and loosened up some, so when we left the restaurant we started bravely walking up Clark Street, until we came to the first bar. Inside we sat down for another drink, because we were feeling loose and free. I said to the waitress, bring us a couple beers! Roxy, gave me a mischievous smile and grabbed the waitresses arm, make it two cum in the hot tub. The waitress laughed and went back to the bar.
I had a huge question mark on my face as she turned back to me. She leaned in and kissed me on the lips, her hot pink lipstick, glossy and inviting. "That isn't an answer" I said after our lips parted.
"Relax babe, you will like these and there isn't anything sexual about them but the name."
When the waitress returned, she had two shot glasses, with amber liquid and what looked like a large drop of cum floating in the center.
I gave her a (way to embarrass me look but she ignored me and lifted her shot for a toast.
"Too large loads of cum!" She giggled and threw hers down.
I followed suit and was so surprised by the taste. Sweet, warm and robust.
She giggled again and rubbed my leg under the booth with her toe.
"That is good, what's in it?"
"Rum, amaretto and a drop of Bailiy's."
Mmmn I said that taste like more, so I caught the waitress's eye and gave her the international signal for one more round.
We chit chatted and soon the second round arrived. We toasted and shot them as well.
I was so enchanted with Roxy, ever since we hooked up several weeks ago; I had really gotten over my fear of the gay lifestyle. I think I had anyway.
We had two more rounds and were feeling quite happy as we tabbed out and floated out into the night air.
Chicago is with out a doubt the greatest city when you are young and in love. We kidded around, pushing each other out toward traffic and stopping for an occasional deep kiss.
Roxy said turn here and let's walk up Broadway.
No problem there, I was light as a feather and in lust.
We hit Broadway and the foot traffic as well as the automobile traffic intensified.
Soon we were in the beginning of the gay bar district, which a month ago would have me hailing a cab. Tonight it was an American in Paris, I figured, I am out with a transvestite, so who better than gays to appreciate us.
Just then a fish net stocking leg, swung out onto the sidewalk and back in again, on a wood swing seat.
I was almost instantly hard.
A woman in black ruffles and black fishnet stockings approached us and more or less hooked us into the bar. Not that I cared, I was ready for some more cum in the hot tub.
Roxy was just as cool as always and followed suit.
I guess I was fairly drunk, or had my drunk goggles on because when we got inside it was obvious that this was a tg bar, more crowded and bawdy then the one I first met Roxy in."
I started to stiffen up and Roxy sensed it, "Honey you are with me and we are among friends, just loosen up and have fun!"
After a soul searching kiss I realized she was right, no one here was going to interrupt a couple in love.
We found a semi-quiet corner and got a couple more shots. They came with a little kidding but none the less they were just a delicious as the others.
Roxy slipped her hand down my crotch and kissed me deeply.
I felt myself rise to the occasion. I kissed her back and returned the favor and because when she was wearing a gaff I couldn't tell but I assumed she was excited as well. Her eyes gleamed with excitement.
I signaled for another round and just then a woman in a red mini skirt and black leggings moved in between us and give Roxy a big wet kiss.
Steve, this is Michelle. We met a few months ago here and she helped me find my living situation."
I smiled and offered my hand but Michelle leaned in and hugged me then kissed me full on the lips. Seeing my reaction, she slipped Roxy a knowing smile and kissed me again, slipping her tongue into my mouth and Frenched me like my first girlfriend.
Michelle laughed and kissed Roxy deeply and went back to the dance floor.
I looked to her, trying to communicate that Michelle had kissed me, not the other way around.
She threw her shoulders into the air like I am not involved and paid the bartenders for the next round.
Suddenly Michelle was back and held my wrist before I could shoot my drink, she removed the shot glass and smiled, if there is any cum to be drunk, I am the girl to do it. Before I could react, she shot the glass and then licked her lips sexily, then out of the blue she said, here Hon, let me share the cum. She deep kissed me again.
I have to admit that her mouth was delicious.
Again I looked at Roxy and again she shrugged and made the sign for 3 more.
Now I was really light headed and loose and I leaned against the bar to watch the scène. There were a good number of leather freaks, both male and "female"
There were some very well dressed women, some I would have been excited by if Roxy wasn't at hand. I actually found my dick to be rigid as I scanned the floor. A couple girls glanced over their date's shoulders and licked their lips at my boner, which made me blush and turn away.
Michelle reached down and grabbed my dick and looked at Roxy,"somebody has a boner!"
Roxy laughed and handed us all a round of drinks and said "Cheers"
Half an hour later we were surrounded by girls, some bawdy, some demure but all caught up in our little tight cluster.
I lost track of the names but I was kissed more than once. I was in a fog of happiness. I wanted the night to go on for ever.
Roxy slowly separated me from the pack and kissed my deeply, "Come on big boy let's go home before you are useless to me.!"
You didn't have to ask me twice.
Roxy kissed me again and whispered, would it be alright if Michelle came with us?"
I was frozen for a second but when I looked into her eyes, I realized that this was her idea and she was into it.
I kissed her again and said,"If you would like that, I can deal with it."
Inside I was feeling greedy since these were the best looking girls in the bar but what ever made Roxy happy was fine with me.
Back at the apartment we were stripping and kissing and rubbing all the way to the bedroom.
I have to admit that Michelle had a wonderful kiss and when her panties came down, she had a seven inch nicely trimmed dick. I gave Roxy a glance which she as much as said, please, she needs it.
I dropped to my knees and went to work on her sweet dick.
Roxy stayed busy finishing undressing me and eventually got to my member.
I was in true ecstasy when the front door lock made a racket and Dianna walked in. She froze in space for a moment until Roxy managed,"Hi Hon, join us if you want!"
My mind registered the words but Michelle was on the verge of Cuming, so I kept at it until she shot a huge load down my throat.
When I recouped, Dianne and Roxy were giving each other head on the bed, so I took Michelle by the hand and we all climbed onto the small bed. As the night went on, we all had a chance to swallow cum and shoot a big load. I may have had a severe hangover the next day but I have a memory most men or women for that matter will never have.
Kisses
Charlene