Please read "Tammy, Lisa, and Karen Part 1" first.
I walked out the store looking at the bag of lingerie in my hand and my cock was so hard, I could barely walk. Lisa wanted me to be pretty for our date. I only had some lipstick and eye shadow at home; I needed to figure out how I was going to make myself pretty for her. That's when I walked past the the answer, but could I really do it?
I was standing in front of the Makeup counter in Dillard's. I guess I was just standing there with a glazed over look on my face, when this 18 or 19 year old red head, maybe 5'4" with pert 36 B cup breasts and nice round ass asked, "Is there something I can help you with?”
Before I had the chance to talk myself out of it I said, "Yes. Can you make me to look like a woman with your makeup?"
I think I shocked her at first, but then she got a great big smile on her face and her nipples instantly poked out of her blouse.
She said, “I think there is a beautiful woman just waiting to come out, let's see where she hiding.”
She said, “I think you should come around back, unless you just want people watching.”
I said, “No lets go to the back.”
“What’s your name?” she asked, as she closed the back room door.
“John,” I replied. “What’s yours?”
“My name is Karen, nice to meet you, John.”
She had me sit on a stool and began by cleaning my face with a damp cloth. Karen then began to apply foundation to my face, neck, and upper chest. I couldn't take my eyes off her nipples poking through her blouse. My cock was so hard from staring at her beautiful breasts. Karen had not missed the fact that I was staring at her chest.
She said with a smile, "Since you like the way they look so much, why don't you feel them? They feel better than they look, I know you want to.”
I instantly had my hands on her pert little breasts. Karen just kept applying my makeup, with a huge smile on her face.
She had me close my eyes, as she put eye shadow, eye liner, and mascara on them. As I sat there with my eyes closed, and my hands on her breasts she asked, “Do you like how they feel?”
“Yes,” I said.
She said, “I bet it doesn't feel as good as this." She unzipped my pants and grabbed my cock. That's when she hiked up her skirt up over her hips. She pulled her thong to the side, dipped two fingers into her sweet nectar, and putting them in my mouth, letting me lick, and suck them clean.
She then pulled off my pants and pulled my cock out of my thong. She sat on my cock burring it in her hot, tight pussy. She slowly rocked back and forth, as she continued to apply my makeup. She finished up my transformation with some bright red lipstick.
She showed me what I looked like in a mirror. "What do you think?”
I said, “It’s great, all of it.” She began to speed up her pelvic thrusts as she put the mirror down.
She kissed me deep, and thrust her tongue into my mouth. I sucked her tongue into mine further, as I probed her mouth with my tongue. My cock was throbbing as she rode me. I could feel every time she clenched down on my cock with her sweet pussy.
I unbuttoned her blouse exposing a white lacy bra. I reached around behind her and unhooked it, freeing her beautiful pert breasts. Her breast had large, dark brown aureolas, and nipples that stuck out a half inch.
I began to kiss her breasts, leaving red lipstick marks all over them. As I started sucking on her nipples she arched her back, backwards and began riding my cock faster. I watched her lipstick covered breast bounce as she road me. I felt my balls tighten, and I exploded in her pussy, just as she came on my cock.
Karen slid off my cock, and sucked it into her mouth cleaning me up. She stood up and said, “Your turn to clean me.”
I just looked at her; she wanted me to lick out my cum from her pussy? I told her, “I have never eaten, my cum.”
She said, “A pretty girl like you has never tasted your cum? Well there is a first time for everything.”
She pulled me off the stool, and pushed me onto my knees. I looked at her beautiful pussy; it was shaved all but a thin patch of red hair at the top. Her pussy was soaked with her cum, and then I saw some of my pearly white cum starting to trickle out. Karen said, “What are you waiting for?” I guess I wasn't moving fast enough for her, she grabbed my hair, and guided my mouth onto her cum filled pussy. My tongue dove in as deep as I could. I completely sucked everything from her sweet pussy. I then fixed her thong.
Karen cleaned the lipstick off her breast, hooked her bra, and buttoned her blouse. She then pulled down her skirt and touched up my makeup.
I bought all the makeup Karen used to make me so pretty, and then headed home. I pulled into the garage, headed to my bedroom, stripped off all my clothes. I then took out the bra with white shear cups, the lace on the edges, and a pink bow in the front, that Lisa loved. I then put on the matching garter and stockings. I dug around in the bag until I found the matching panties. I slid them up my stoking clad legs; I tucked my cock under, and pulled them up over my ass.
I put some perfume between my little breasts and on my wrists. I dug in my shopping bag again pulling out my new blouse, and skirt. I put on my semi shear top and buttoned it up, leaving the top few buttons undone. You could see my bra through my top. I pulled up the mini skirt and zipped it. Lisa was so right, my ass looked great plus it showed off my legs. I slipped my feet into a pair of open toe, red and black high heels. I finally brushed out my wig and put it on, the look was complete.
I drove to the mall and arrived at 9 o'clock. I called Lisa to tell her I was there.
She said, "Wonderful, drive around back to door number 71 and wait for me." I found the door to her store, and then got out to wait on her. As the door opened I expected to see Lisa and the other sales ladies from the store, but the first person out was Karen.
She smiled at me and said, "Hi Tammy, it is nice to finally meet you, formally." Next out the door was Lisa smiling at me,
"I see you have met my daughter, Karen." I didn't know if Lisa knew what happened between Karen and me.
That's when Lisa asked me "Did you enjoy Karen's tight pussy as she did your makeup today?" I looked into this beautiful woman's eyes, knowing she knew everything that had happened.
Lisa just smiled and said, "Just keep in mind Tammy, you’re my girlfriend, not hers."
Lisa said, "I know Karen can be persuasive when she wants to be, but if something like that is ever going to happen, I will let you know when and where, ok?" I just shook my head yes.
I could not believe it; she just called me her girlfriend. I’m Lisa’s girlfriend. Lisa tossed Karen her car keys and said, "We’ll be home later." I led Lisa to my car and she told me where to drive. After several turns down roads I have never been on we finally stopped at a night club. I was frozen, I couldn't go in dressed like this. Lisa got out, walked around the car, opened my door, and took my hand; as if she knew what I was thinking. Squeezing it she said, “You’re coming in!”
As we walked in, arm and arm, I saw it was a cross dresser, and transvestite friendly night club. Lisa told me she brought me here just to show me off. She wanted to make her friend, the owner of the bar jealous. The owner was another beautiful woman named Trish. Trish was wearing a corset that pushed up her ample breasts, and black slacks that looked like she had been poured into. Trish had long black hair to the middle of her back. On her pouty lips she wore my favorite bright red lipstick. Lisa said, "Trish, I want to introduce you to Tammy, my new girlfriend."
Smiling at me Trish gave me a kiss on the lips, "Nice to meet you Tammy."
Trish then told Lisa, as she looked me up and down "If you ever want to give her up, just let me know."
Lisa said, "I think Karen already has dibs on her,"and the two women laughed.
I couldn't believe it, I had been looking for a woman to accept me like this for years, now I have found three in one day.
After several hours of drinking and dancing we headed for Lisa's home. We walked in the front door; Karen was sitting on the couch in just a lavender baby doll with a matching G-string. Lisa said to her, "nice try baby, but Tammy is mine."
"Oh mom, can’t you share?" said Karen.
"Not tonight, you are going to have to take care of your own needs, there are plenty of girlie boys out there."
Lisa led me to her bedroom; shut the door, put on some romantic music. She walked up and pulled me close and kissed me softly on my lips. She felt my right breast with her left hand, her right hand unzipped my mini skirt and slid it in and cupped my ass. We kissed deeper as she played with my pantie covered ass, and pinched my nipples through my bra. She stood back and unbuttoned my blouse, slid it off my arms, letting it fall to the floor. She then hooked her thumbs in my skirt and slid it down my legs.
I started to unbutton her blouse, but she pushed my hands away. She began to do a strip tease for me. When her blouse came off I saw her wearing the same bra as me. She unzipped her skirt, let it fall to the floor, there we stood in matching lingerie. I thought to myself, 'Oh my god does this woman know what she is doing to me?'
Lisa said, "I decided it looked so good on you today, I just had to have too. What do you think love?"
I said, "You’re the sexiest woman I have ever known." Seeing her dressed the same way as me turned me on more than I ever thought I could be. Lisa started to kissing me as she walked me backwards towards her bed, before I knew it she had me on my back and was climbing on top of me. We started kissing all over each others bodies.
I reached around, unhooked her bra freeing two of the most beautiful breasts I had ever seen. Her hand was on my seven inch boy clit. "Is my Tammy a virgin?" she said as she played with my rose bud.
"Yes." Lisa got a big grin on her face as she pulled off her panties. She opened a hope chest at the end of her bed, and pulled out a strap-on.
"Come here lover, I'm going to take your cherry. Do you want that?"
"Yes Lisa, please take me. I'm all yours" I said.
Lisa said that I needed to give her a real good blow job before she would give me what I wanted. I got on my knees and started to lick, and suck her hard rubber cock. It must have been nine inches long, but I could only get about half of it in my mouth.
Lisa said, "You’re going to have to do better than that. You’re going to take all my cock in your mouth and up your boy pussy." She started telling me how to deep throat her cock until, the rubber balls were hitting my chin. She said, "You’re such a good cock sucker Tammy."
Lisa stood me up and took my panties off. "Get on the bed, on all fours." I felt Lisa lube up my ass and insert two fingers. She reached around and found my hard boy clit, she started stroking it. She then slipped in a third finger, working me a bit more. She pulled her fingers out and put lube on her cock.
Lisa said, "Now just relax, I'll be easy," she then pressed her hard cock into my virgin ass. It hurt as she first went in, she buried all nine inches of it me, and she then let me relax a bit before the assault on my boy pussy began. Lisa then started to slide her cock in an out of my tight, rose bud, slow at first, but picking up speed soon after. Lisa held on to both of my hips, as she rammed her cock into me. The more she fucked me, the better it felt. I couldn't believe it. I felt my balls tighten as she fucked my ass; I was going to have an orgasm without even touching my cock. That's when I erupted all over the bed covers. Lisa felt me cum and began to cum herself.
Lisa pulled out and removed her strap-on. When she saw the mess I made on the bed.
"You made that mess, get down there an lick it up like a good girl." I instantly licked up all the cum. Lisa started to lick my soft, limp, boy clit, sucking it in her mouth, using her tongue she got me hard, she then straddled me, slid her hot wet pussy on my boy clit.
I am so turned on by this woman, we are still wearing our matching garters and stockings. I still have my bra on and she was on top of me riding me as I held her breasts. I felt her orgasm as she shook and screamed out, "Tammy, oh Tammy."
I am not far behind her, "Don't stop, Lisa, don't stop, oh yessss." I came deep in her pussy filling her up with my cum.
Lisa pulled off, spun around into a 69 position, and for the second time in a day I was eating my cum from a woman’s pussy. Lisa cleaned off my boy clit, after I had swallowed both our cum, she turned around and we slid under the covers. She got behind me and we spooned, with her leg over mine, and her hand in my bra, we fell asleep.
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<a href="https://www.lushstories.com/stories/crossdressing/tammy-lisa-and-karen-part-2.aspx">Tammy, Lisa, and Karen part 2</a>