Stephanie and I had spent a very nice and exhausting afternoon in my bed. Walt was taking us to supper later and Steph was looking through my clothes for something nice to wear. She is a little fuller than and was having difficulty finding anything that looked nice on her. She finally found a skirt and blouse that looked good on her.
“Don’t you have anything nice that’s not sexy?” she complained. “Almost everything you have screams ‘Fuck Me’! Don’t you get tired of having strange men making passes at you?”
I shrugged. My first outfit was intended to help me seduce my high school friend. I also had a few Hello Kitty tops and panties I wore around Dave, my first lover. I had several tank tees and denim cutoffs. Walt liked seeing me in these! Jackie and Silve had helped me pick out then rest of my outfits.
As we were leaving, Stephanie asked Walt if he would mind running by her place. He waited in her living room as she dragged me into her bedroom. She rummaged through her closet and found a nice, knee length dress. She had outgrown it and, while it was little large on me, it still looked good.
Walt whistled when I entered the room and said, “That looks lovely on you!” I was a little embarrassed, but secretly pleased.
“Next week, I’d like Angie to spend the night. I’m taking her shopping for some new outfits. Get your VISA ready!” Stephanie exclaimed.
“I’ve been trying to get her to buy anything she wants, but she spends very little on herself!” he exclaimed.
I grew up with little extra money so I’m very cautious. Miguel complained because I barely touched my allowance when I was his mistress. Not spending his money used to upset him. we often fought about that until i moved in with Walt. I don’t even spend all the interest on my trust fund. While Walt is well off and financially secure, I don’t want to be frivolous. Both my lovers told me they are supposed to spend money on their trophy girlfriends!
The following week, as I headed out, Walt handed me his Gold Card and told me to have fun and buy lots of clothes. I could also buy something for Stephanie as a ‘Thank You’ if I liked. Stephanie picked me up and drove to a very upscale lingerie store. She told me they were used to serving transsexuals and were very discreet.
“While slutty outfits are nice, men like Walt and Roger prefer classy,” she informed me.
The clerk, a very tall and lovely black woman, had me remove my bra and panties then took several measurements. I hadn’t been naked before a stranger in a very long time, but she was very professional. She had me model several sets before she found two or three styles that would be flattering. I tried on a set that was very comfortable, and I liked what I saw in the mirror.
The clerk asked Steph what she thought. Steph came up to me and fondled my breasts through the bra. She then pulled me close to kiss me, reaching behind to release the clasps. She ran her hands down my side and across my bottom.
“I think her boyfriend will love these,” she said.
The clerk, Monique, was helping me fit my new bra. Stephanie had stepped out for a few minutes. As I looked in the mirror, she leaned over and nuzzled my neck. She slid one bra strap off my shoulder and kissed there, too. I must have moaned encouragingly.
“You have a beautiful bottom. May I…….?” she asked before she slid my panties down and knelt behind me. She kissed my bottom and lightly caressed me. I sprang to attention. She turned me around, looked at my cock and sucked me gently. I came quickly!
“That was nice. Thank you”, she said and left the fitting room.
I ended up purchasing several styles and colors to wear with the new dresses I would be buying. I also bought a couple of sets I thought might look good on Stephanie. She was pleased with her gifts. After all, I’m her lover and I should spend on her, too!
We stopped for coffee and Stephanie asked what had happened. I told her and she whistled appreciatively. She told me Monique had done the same for her a couple of times. We fantasized what it would be like to have a threesome with her, but couldn’t figure out the best way to approach her.
Our next few stops were to find dresses, skirts and blouses. My current dresses include my very sexy and revealing gowns and short dresses. Mainly the ones I wore for Miguel’s pleasure. I had blouses and tight skirts I wore when working for Jackie and teaching college classes. I also had a few bright sundresses. I like dark blue. Stephanie said I needed two or three black dresses and some with different colors, for different occasions.All were short sleeved. One fell below the knee, one above the knee, and a couple fell mid-thigh. None showed exposed cleavage. I would have to bend over for Walt to get a peek at my breasts. I felt beautiful and classy at the same time. I had Steph try on one similar to my favorite. We both liked how it looked and thought about going out together like this. I told her Walt was paying. We found other dresses in different colors and styles for every day wear. We found a few blouses I liked.
After a late lunch, we bought shoes. I bought two pairs of tall spiked heel boots, regular high heels, some flats and some sandals. I insisted on a few pairs of colored sneakers.
Next came dressy slacks and nice designer jeans, then some nice sweaters. I was beginning to feel guilty. I had spent at least three months’ salary from my job at Jackie’s! If Walt was concerned, I would repay him from my funds. I called and asked Mrs. Daly, his secretary, for advice. I gave her the total and she laughed. I wasn’t even close to what he would allow! Walt’s ex-wife spent 2-3 times that amount every month.
“Go buy some really nice jewelry.” Wren advised. “He wants to buy you some, but is really clueless to what you like. He wants to take you to company and client functions and show you off. Walt is so proud of you! And I’m so pleased he found you!”
I bought a simple, yet elegant, necklace, a bracelet, and earrings. I bought a nice necklace for Stephanie.
We went to a little café and ordered some beers. Stephanie was pleased with my choices, then asked me about sleepwear.
“I wear Walt’s old tee shirts, when I don’t sleep naked.”
“Don’t you have any nice and sexy gowns?” When I shrugged no, she decided to return to the lingerie shop. I bought several long elegant gowns, some teddies, and a few short gowns, all in black, or dark blue. I intended to wear them long enough for Walt to remove them!
Stephanie asked for Monique, but she’d already left. The other clerk said she’d left a note if we came back. It had her phone number. We called and made arrangements for dinner.
Over dinner, we learned that Monique was a dominant transsexual. She lived with another dominant tranny and shared a submissive live in boy toy. She definitely seemed interested in us. We invited her to my old apartment, but she preferred her place instead. Monique reminded us she was a top and if she joined us, she would fuck both us. We would also do what she asked. She then laughed and said she only did the rough stuff with her “toy”.
Monique greeted us at the door and invited us in. Her partner, Gabrielle, was seated at their bar with her dress pulled up to her waist and her ass hanging over the back. Kneeling behind her was Craig, their boy toy. His wrists were manacled behind him and he was eating her ass with great enthusiasm! Gabrielle came over and hugged us both, and Craig said hello. We sat around making small talk. Craig by the stool, still manacled. Gabrielle was a smaller, full-figured, older tranny, near Jackie’s age. She knew Jackie professionally. Gabrielle was a professional dominatrix. She was home this evening because her appointment rescheduled. She also had a nice fat cock, maybe seven inches long.
“Craig didn’t clean the kitchen very well. I need to have a few ‘words’ with him,” Gabrielle grinned wickedly. Craig’s smile covered his face.
Monique took us on a tour of their loft while Gabrielle attended to Craig. We could hear loud swats and Craig saying “Thank you, Mistress. Harder please, Mistress.”
Steph and I wondered what we had let ourselves in for. Monique laughed and said, “We only play rough with the boys, not little girls like you.” Little girls like us???
Monique showed us the master bedroom. There was a small bed similar to a bed for a very large dog at the foot of their huge bed. Monique told us Craig slept there, ready to service either one should they require. The second room was set up like a massage parlor with two tables.
We returned to the main room. Craig presented his ass to Monique, who promptly said he wasn’t red enough yet. He smiled brightly as he looked at Gabrielle and mouthed, “I told you so!” Hmm! I wonder exactly who is servicing who? Monique had us undress. The room was suddenly full of cock: two dominate trannies, two transgendered women, and a really strange boy toy! Monique positioned me and Steph doggy style. Craig proceeded to eat both our asses, alternating between them while the tops stroked themselves and watched. While this felt very good, Steph and I were a little uncomfortable.
Monique had me turn around. She had the choice of Stephanie’s ass or my mouth. Gabrielle was on the other side. Monique pushed her cock in my face, wanting me to suck. I could feel Gabrielle pushing into my ass. While both cocks were thick, they didn’t compare with Walt’s. I wouldn’t have any problem, but Steph might. Roger has a narrow cock. If she didn’t want to do it, I would handle both. I had a lot of experience from when I worked for Jackie.
Suddenly, Stephanie got up and backed away, a terrified look on her face!
“Angie, I want to go home, now. Please! Take me home?” she begged.
I didn’t like the looks I saw on Monique and Gabrielle. I stood up and thanked them, but politely said we were leaving Monique just waved us off and pulled Craig down to where I had just been! She forced her fat cock down his throat and started face fucking him!Gabrielle rammed her cock into his ass and was fucking him hard.
“Goodnight, little girls,” theyc alled mockingly after us. We could hear their laughter after we shut the door.
We hurriedly dressed in the hall and ran to the car. Stephanie was sobbing uncontrollably and handed me he rkeys. She cried all the way home and didn’t stop until we got to her place. The terror had passed, but I saw great sorrow in her eyes. I asked her what was wrong. She just had me sit on the couch and then sat on my lap like I did on Walt’s.I held her close as she continued crying. She cried for nearly an hour. I was really worried and offered to call Roger. She quickly shook her head no. After a moment, she told me her story.
“When I was young, my father and brothers dressed my like a woman and repeatedly raped me. I ran away from home and worked as a prostitute before I met Roger. I used to let men, women, and other trannies use me like they were using Craig! Seeing them reminded me too much of my past!”
She got up and led me to her room.
“Please, just hold me tonight?” she asked. I lay by her as she cried herself to sleep. “You’re the best friend I’ve ever had,” she said.
The next morning, the old, ready-to-face-anything Stephanie was back.
“Ready to go shopping?” she smiled and headed to the door.
----to be continued----