

My Dream Girl
Part 3

Two weeks later, while I sat at my desk at work, cruising porn sites on my computer, my 
secretary buzzed me and said that Mr. Luther Jones was on the phone. I picked up and 
said “hello”. Luther said “Hey Joe, How’s it going. I’m surprised that I haven’t heard 
from you. Lisa said that you guys had a “good interview”.  She expected to hear back 
from you before now.” I replied that I had been busy. Luther came back with “Lisa’s not 
busy this afternoon. Why don’t I pick you up at 2:00 PM.?” I said ‘Well I don’t know. 
I’ve got a lot of work to do.” Luther jumped back with “Come on Joe. A little break will 
do you good. I’ll have you back in an hour. Lisa really wants to see you.” I gave into the 
pressure and said “OK”. Luther drove me to the Marriot and gave me the phony suitcase. 
I called him back with the room number and waited. I was nervous and excited about the 
events to come. When Lisa arrived, she looked even more beautiful than the last time. 
She was dressed like a young business woman in a grey suit. She had matching shoes 
with 3 inch heels which made her a lot taller than I am. She immediately embraced me, 
kissed me on the lips and forced her tongue into my mouth. As she held me tightly with 
my head tilted back slightly because of her height, she continued to probe my mouth with 
her tongue. I realized it was clearly an assertion of her dominance but I couldn’t help 
enjoying it. In fact, I found myself getting really turned on. When Lisa finally pulled 
away, she said “Help me get my clothes off, Joe” After she took off her suit jacket and 
hung it in the closet, I unbuttoned her blouse and helped her get it off. I hung it in on a 
hanger in the closet.  She turned around so that I could unhook her bra. She pulled out of 
the shoulder straps and let the bra fall to the floor exposing her small breasts. It boggled 
my mind to think that this beautiful feminine creature was really a man. I lowered my 
mouth to her lovely breast and took her nipple into my mouth. She moaned while I 
sucked. Then she moved my mouth to her other nipple and as I started sucking she said 
“Oh yes, that’s a good boy. Now take off your clothes, baby”. I sucked a moment longer 
and then pulled away. I quickly removed my clothes and left them on the floor. Lisa 
stood up took off her high heels, skirt, pantyhose and panties. I looked at Lisa’s big black 
cock and saw that it was partially aroused. We sat on the edge of the bed and kissed until 
Lisa started to push my head down. I suckled on her nipples for a minute of so. I was 
getting really turned on by the encounter. Then she pushed me down towards her cock 
saying “That’s a good boy, Joe. Now suck it for me just like you did last time. It’ll be 
OK. Just open your mouth.” I barely opened my mouth. Lisa held the back of my head 
and pushed down until the head of her cock slid between my lips and into my mouth.  
She didn’t have to tell me to suck this time. I knew what she expected. It was much easier 
for me, mentally, to perform for her. After a couple of minutes, Lisa told me to kneel on 
the floor between her legs. I was more comfortable in this position and it was easier to 
work on her cock. Part of me felt really sick about what I was doing. But another part of 
me felt an emotional connection to this man/woman and I wanted to give him/her 
pleasure. I looked up at her beautiful feminine face. She wore the perfect amount of 
makeup. Her lips were painted red. But not a flashy colored red. She looked at me and 
smiled. Her perfect white teeth contrasted against her black face. It was easy to see that 
she was a lot younger than I am. As my head bobbed up and down on the growing cock, 
she started talking to me saying “Joe. I like to be open and honest about things. That way, 
people know what is going to happen and what is expected of them. When two people get 
together for sex and one is a man, they work together to make the man cum. Both 
participants make this the goal and take pleasure from the act of achieving it. A lot of 
times, the participants are a man and woman. The woman uses her mouth, her pussy and 
whatever else she has to get the man’s seed. Sometimes she has an orgasm, but the real 
point is to work together to get the man to cum. Sometimes this is to impregnate the 
woman and sometimes not. Now you would think, with my feminine side being so 
prominent, that I might take the servicer side in our relationship. But look at you Joe. 
You have a cock that’s too small to be any good to anyone. The rest of your body is pale 
and frail. So when we get together, it will be to work on my cock. It will be an 
opportunity for you to experience a big cock.” My efforts had gotten Lisa cock to its full 
size and her hip were bucking in unison with my bobbing head. The precum was building 
up in my mouth and I fought to swallow it down. After a few moments she continued 
saying “From now on we will be getting together twice a week, on Tuesday and Thursday 
afternoons. I have worked with other white men who are under endowed in one way or 
another, so I know how to structure your training to maximize the pleasure that we will 
both receive. We will start with simple blow jobs like the one you are giving me right 
now. As you progress, we will move onto other positions and other techniques like deep 
throating. When your oral skills have progressed sufficiently, we will work on your anal 
lovemaking skills.” As I starting involuntarily making slurping noises because of juices 
that were building up in my mouth, I thought Lisa was crazy. I had no intention of 
making our interaction a regular thing. However my cock was betraying me. I had a 
raging hard on. As I reached down and stroked it, I realized that it was harder than I can 
ever remember it being. Lisa started talking again saying “I like this hotel, but the desk 
clerk will catch on if we keep meeting here. From now on we will meet at my place. My 
boyfriend and I have a place not far from here. Don’t worry. He won’t be around when 
you visit. I don’t feel right about you paying me cash for our little get togethers any 
more.” She stopped talking. I continued slurping and she started making little moaning 
sounds. I could tell that she was getting close. Looking down she said “I make a lot of 
precum don’t I, Joe? I know how that is. My boyfriend is that way too. Why don’t you 
pull off and swallow?” I pulled off and swallowed the spit and whatever that accumulated 
in my mouth and coated my throat. When I had finished swallowing the mess and took 
her cock back into my mouth, she continued “Now we are ready to share an orgasm. I 
want you to look in my eyes as we share the moment.” Lisa and I locked our eyes as we 
continued to work towards her orgasm. In less than a minute she pulled back a little and 
started shooting in my mouth. Between he moans of pleasure she said “That’s a good 
boy. Now don’t spill a drop.” When Lisa finished cumming and our eyes still locked, I 
pulled back and swallowed. The slimy texture almost gagged me and the salty bitter taste 
was disgusting, but I got it down. She pulled me forward onto her softening cock and said 
“Now jerk off for me, Joe” With our eyes still locked and the softening cock in my 
mouth, I jerked until I shot my load onto the carpet. My orgasm was intense and the 
pleasure spread throughout my body. Lisa suggested that we cuddle in bed for a while. I 
crawled in beside her and she pulled my head to her breasts and laid there for the better 
part of an hour. When we revived, she suggested we take a shower together. At her 
direction, I used soap and a washcloth to clean her entire body. When I finished, she 
gently pushed me to my knees and I sucked her off again while the warm water spayed 
on us. It really didn’t take her that long to cum considering she shot her load an hour 
earlier. However, the volume of semen was a lot less and I had no problem swallowing it. 
As I knelt there, I couldn’t believe that I was pondering how long it took for her to 
ejaculate and the amount of cum I was swallowing. What the hell was I doing sucking off 
a transvestite or anyone else for that matter? I knew that my slight body and little cock 
did not qualify me to be a real stud. But wasn’t I a man who liked to fuck women? Then 
again, didn’t I let my wife humiliate me by feeding me my own cum and that of her 
lovers? At least this time my cock did not get hard while I serviced Lisa. After the shower 
we got dressed in silence. Lisa had that glow of a person who is sexual satisfied. She 
called Luther and told him I was ready to go back to work. I took out my wallet and 
started to pull some cash out. Lisa told me to stop. She said that I wouldn’t be giving her 
cash any more. But there was another way that I could help her. She said that it’s hard for 
a transvestite to get a regular job, so she was a little behind on her bills. She said that it 
would be great if I could help her out with her Visa bill. She handed me the unopened 
envelope as I left. When I got back to the office, I opened the bill and saw that with late 
charges the amount due was just over $2400.00. I told myself that there was no way that I 
was going to pay. As I looked through the bill, I noticed that there were charges for 
clothes, hair salons, nail manicures, and trendy restaurants. Other than the late charges, 
the bill was similar to the one my wife ran up each month. The next day, I went to my 
bank and withdrew $2500.00 in cash. Then I went to a check cashing place and bought a 
money order for the amount of the Visa bill. I walked to the post office down the street 
from my office and mailed the payment in an envelope with no return address. 



Continued in Part4

Please address any comments or encouragements to jcbottom@hotmail.com


