As is the case with most closeted cross-dressers, getting nice sexy women’s clothing and lingerie is often difficult, to say the least. One day when I went to the laundry room in my apartment complex, I found the hottest pair of panties I ever laid eyes on left in the dryer. I immediately pulled them out and put them on the bottom of my clothes basket. As soon as I got back to my apartment, I took off my sweat pants and undershorts and put on the panties. I was in heaven. I spent the remainder of the day walking around my apartment in just the panties and a long oversized tee shirt.
Up until then, all I had were a few pairs of not so sexy panties and an aging bra left from an old girlfriend. I couldn’t get over how great I felt in the newfound panties. I wore them every opportunity I had, which required regularly washing them. It was then I knew I needed a more extensive wardrobe. I also realized that my new panties would eventually wear out.
In the past, I would always gaze at the lingerie as I passed by the ladies' area in the department store. Sometimes, I would deliberately wander the store making multiple passes. Other times, I would go into the area across from the ladies' wear where I could get a longer look, at a distance, without being noticed. In any event, there didn’t seem to be a way to shop for what I wanted, let alone pay for any purchases at the register if I did pick something out. So close, yet so far.
The next week I needed to pick up some toiletries so I went to my neighborhood department store. As always, I walked past the ladies' wear on my way to the personal care aisles. I picked out some soap and shampoo, placing them in my cart. Then, I walked the long way to the checkout, passing by the ladies' wear once more. The store was busy and one of the workers suggested I use the self-checkout. It was the first time I ever used one and was pleasantly surprised at how convenient it was. As I was scanning my items, I noticed that the lady at the next kiosk was scanning some clothing. The light bulb over my head came on.
That night I drove to another department store several miles from my apartment. It was much larger and had two self-checkout areas with a dozen kiosks each on either end of the store. I got a cart and walked by the ladies' wear. The store was not crowded and there was hardly anyone in the lingerie area. I went to the men’s wear first and put a pair of blue jeans in the cart. Then, I went back and milled around the lingerie, waiting for an opportunity. I figured I would quickly pick out something and put it under the jeans to hide them until I got to the checkout, then quickly scan them and put them in a bag.
When there was no one around, I pushed my cart next to the open panty rack and started to look at the vast selection. I felt like a woman in the fact that I couldn’t make up my mind. As I became infatuated with their inventory, I realized that a woman was close behind me. I pushed my cart towards the ladies' jeans, waiting for her to move on.
As soon as she moved out of the area, I moved back in, only to have another woman take her place. This went on for twenty minutes, frustrating me, since I now wanted some new sexy panties desperately. The next opportunity, I moved in next to the rack. Again, another woman moved toward me. As I started to move, she asked, “Hi, Sweetie, could you be a dear and help me a little?”
I gave her a puzzled look as I replied, “I guess, what can I do for you?”
“I want to buy some sexy panties and I was hoping to get a man’s opinion since that’s who will look at them the most.” She looked at my expression. “I’m so sorry, Sweetie, I didn’t mean to embarrass you.”
I stuttered, “That… that’s okay. No need to be sorry. I guess I’m just a little bit of a prude.”
She picked up a pair of hot red panties with black lace around the waist and legs as she asked, “What do you think of these? Do you think this will get a rise?”
I couldn’t believe how forward yet nonchalant she was. I answered, “They are quite sexy.”
“Why don’t you pick out a few that you like for me?”
It was like a dream. I couldn’t believe this woman was asking me to help her shop for panties. One part of me was excited and about to explode; the other part was scared and embarrassed. She took my one hand and held it against her thigh as she pushed her right breast into my arm. I picked up a lacy thong and handed it to her.
She spread it out on the top of the display rack. “You have excellent taste, Sweetie. I like these, too.” She threw them into her cart. “Pick out a few more for me.”
Before I knew it, we were both sorting through the panties, showing them to each other and asking for comments. This went on for at least fifteen minutes until she had a half dozen pairs in her cart. Finally, she said, “I need a bra, too. Let’s go over and look at them.”
Still in a somewhat state of disbelief, we walked over to the bra section with our carts. She stopped at a rack where the bras were hanging individually on display. As she started touching a few of them, she looked at me and asked, “If you had to wear a bra, which one would you pick out?”
I looked at her with a new wave of embarrassment, trying to find an appropriate answer. “I...I don’t know.” Pleading the fifth, I further answered, “How would I know?”
“Oh, come on. Bras are the same as panties. They are as attractive to the viewer as they are to the wearer. Help me out and pick one, please?”
She wasn’t taking ‘no’ for an answer. I looked at them carefully before picking out a black one with individually formed cups, red lace trim, and a red embroidered rose between the cups. It was giving me a hard-on looking at it. She motioned for me to take it off the rack and give it to her.
As I handed it to her, she remarked, “Another good choice. I love it. Don’t you like helping me pick out intimates? You have such great taste.”
I answered, “Yeah, I guess so. I’m just still a little embarrassed.”
She took both my hands in hers as she replied, “Would you feel better if I modeled this in the privacy of my apartment?”
At this point, I was in total shock. I thought for sure I was dreaming or it was a trap for some diabolical plan to kidnap and murder me. It was an offer that required careful consideration, yet she was waiting for an answer.
After a long awkward minute of silence, she looked directly into my eyes and said, “I’m sorry, Sweetie, maybe I should clear something up for you.” With my hands still in hers, she pulled my hand into her tight jean-covered crotch, rubbing it around. She was right. It was clear now. She was a he.
With a very sincere look, she asked, “Are you disappointed? Are you mad? I just wanted to help you. I went through the same thing years ago.”
A thousand different thoughts went through my head. I felt like a slot machine with my wheels spinning, but when they stopped, there were three windows showing. I enjoyed looking at the intimates with her, I was excited, and my hand was still in her crotch.
“I’m sorry,” I answered. “You took me by surprise. I would have never guessed. You look so good as a woman.”
“Thank you, Sweetie, I think.”
“Please, I meant it as a compliment. I wish I could look as good as you.”
“Does that mean you’ll let me model for you? I think you could look and feel as good as me. We are probably the same size. You can pay me for the items you like and take them home with you.”
I don’t know why I was hesitating. This was a golden opportunity to get what I originally came to the store for. I smiled, “Tonight?”
She smiled broadly, “Yes, Sweetie, tonight. Is there anything else you want to look at before we go?”
I told her, “Not tonight.”
We went to the self-checkout and scanned everything. I insisted on paying for it all. Then, she instructed me to follow her in my car to her apartment. She lived about ten minutes from the store in the opposite direction from my apartment. It was in a quaint complex with units in clusters of four along a stream. Each unit had its own private parking for two cars, so we parked within steps of the front door.
I walked over to her car, took the shopping bag from her, and carried it to the door. I thought to myself, she is clearly the woman and me, the man. She unlocked and opened the front door. As we entered, I realized I didn’t even know her name. As excited as I was, I still felt quite awkward in so many ways. Thankfully, she continued to make me feel comfortable by taking the lead.
“Well, Sweetie, let’s get comfortable and get to know each other. Oh, by the way, I’m Tiffany. What’s your name?”
Without thinking, I replied, “Shawn.”
“Can I get you a drink, Shawn? Water, soda, wine? How about some good scotch.”
Once again, I followed her lead. “The scotch sounds good.”
She put some ice in two glasses, followed by the scotch and some water. It didn’t seem like a very feminine drink in spite of her obvious feminine looks. After handing me a glass, she took a sip of hers before taking my hand, leading me down a short hallway to her bedroom. Her feminine side was obvious in her bedroom. The walls were a light pink; the bed was a combination of pink and white satin covers and pillows. There was a large vanity on one wall with two velvet cushioned seats and ‘Tiffy’ scrolled across the wall in fancy lettering. There was a large walk-in closet and an attached bathroom on the other side. She took both our glasses and set them on coasters on the vanity top as she said, “It's gurl time, Sweetie.”
She pushed her shoes off on the floor using her feet as she began unbuttoning her blouse. With her blouse still on and wide open, she wiggled her jeans down her legs to the floor before stepping out of them. With the exception of the bulge in her panties, she still looked every bit a beautiful woman. She took off her blouse, laying it on her bed. Then, she slowly turned around one complete revolution. “Well, Sweetie. What do you think? Like what you see?”
Still feeling a little awkward, yet needing to encourage her to continue her efforts, I responded, “Yes, you are . . . Uh . . .stunning. I’m quite impressed. But, how?” I was so confused and it must have been obvious to her.
Once, again, she rescued me from myself. “It’s a combination of hormones, breast enhancement, constant skin care, make-up, hair styling, and voice training. But probably most important is attitude, appreciation, and observation. I have carefully watched biological females for years, watching their every move, appreciating everything they do, and changing my attitude to be the same as theirs.”
This was pretty deep, but I suddenly found myself captivated by her and what she was saying. I had to ask her, “Were you feminine-looking before?”
“Not really,” she answered. “I saw a lot of before and after pictures of others who transitioned. I was inspired by so many of them. It made me believe that it was possible, even for me.”
All my tensions were dissolving and my mind seemed to focus clearly as I intuitively inquired, “Do you think I could change like you did?” I thought to myself: Did I really just ask that question?
Tiffany’s face lit up and a big smile ran across her face, “Oh, Sweetie, absolutely. It would be so much easier for you because I would be there to help you all the way. I would be your BFF, dear.” Then she gave me a big hug. “Let’s move slow starting off tonight and let you ease into it. If you change your mind, I’ll understand. I’ll still be your BFF.”
She reached down to the bottom of my shirt and pulled it up over my head. Neatly folding the shirt, she set it on the small night table next to the bed. “Take off your shoes, Honey.” After removing them, she grasped my waistband and pulled down my sweat pants. An hour ago I would have been horrified at the prospect of someone seeing me in a pair of panties. But, Tiffany changed that. “I love your panties. You have such wonderful taste.” I was actually beaming at her compliment.
She emptied the bag from the store out on the bed, picking up the bra we purchased. “Let’s try this on you. Turn around and hold your arms out.” She slipped the bra up my arms, then walked behind me and pulled it on me, hooking the rear clasps.
“I knew we were the same size. It fits you perfectly. How does it feel?”
For the first time tonight, I could talk freely without the apprehension I harbored since meeting her, “Oh, it feels so absolutely wonderful, Tif.” I immediately began to understand her comment about the attitude. My choice of words was so female. They made me feel more feminine just saying them. “I can only imagine how good you must feel with your breasts.”
She took my hands in hers and placed them on her breasts. “They do make such a difference. Let me take my bra off for you.” She reached her hands behind her and unhooked the bra before letting it slide down her arms, tossing it on the bed. Again, she took my hands in hers and held them on her naked breasts.
They were firm, yet the skin was soft, perfectly formed, and perky, with prominent nipples. They were proportional in size to her body, not too big, not too small. While I have seen and touched women’s breasts before, I was never encouraged nor had the opportunity to study them so closely. She put her hands on my head and pulled my mouth to her right nipple. I began to lick, then gently suck it. She gripped my head tightly, leaned her head back, and let out a moan.
“I’m sorry, Sweetie. I lose control when that happens. They are so sensitive. I’m so glad I only got small enhancements and let the hormones do their thing. Let’s see how sensitive you are.”
She pulled my bra up and started licking, then sucking my right tit. I never had anyone do that to me before. I couldn’t believe how good it felt. I began cooing like a little girl.
She looked up and smiled at me, “We are so much alike. You’re as sensitive as I am. It’s so much more fun being a gurl, isn’t it? Have you ever had anal or oral sex? Giving or receiving?”
Each time I reached a level of comfort, she kicked it up another notch. I took a couple of sips of my drink as I thought about her question. It was clear she was waiting for an answer, so I obliged her, “I’ve gotten a blow job a few times.”
“Have you ever imagined having sex with a man? Do you want to explore that a little? You know you can trust me, don’t you? I really am your BFF.”
At this point it was all out on the table. I not only trusted her, I wanted her to lead me down a road that I had often envisioned in my dreams. I couldn’t imagine anyone more genuine than her. I opened my closet to her, “Yes, I have imagined what it must be like for a woman to have sex with a man. Yes, I would like to explore it with you. And, yes, I feel so fortunate to have met you tonight. I never imagined having a BFF, let alone one as amazing as you.” I gave her a small kiss on her cheek.
She told me to lie on my back in her bed. Then, she began rubbing my cock through my panties. I was already hard and had a sizable wet spot. She pulled my panties down to my thighs before licking the precum oozing from my cock. She expertly used her tongue around the tip before moving down my shaft. Her mouth was like an oven inside as it engulfed me. After moving up and down my shaft a few minutes, she pushed her head down to the point where I could feel my cock going down her throat. I let out a moan. She quickly lifted her head up, letting me spring free.
Then, she walked to the night table and took out a small packet, tearing it open. It was a condom, which she rolled onto my cock. At first, I thought she was going to finish blowing me with the condom on. But, then she climbed up on the bed, pulled her panties down to her thighs, straddled me, and lined my cock up with her ass, all the time looking directly into my eyes. She eased her weight down on me, forcing my dick into her warm and tight ass. I couldn’t believe the sensation. When her ass cheeks rested tightly on the top of my thighs, she leaned back a little and just sat there motionless.
“I don’t want you to cum just yet. I want to enjoy the feeling of you so deep inside me. How do you feel, Sweetie?”
“I never felt anything this good in my life. It’s amazing,” I answered.
With a big smile and look of contentment, she replied, “It’s not as amazing as I’m feeling right now. Is this your first time for anal sex?”
“Yes, I guess it is.”
“When you’re ready, I’ll teach you how to take it in the ass. The advantage of being a T-gurl is we know what men like. How does this feel?”
With that, she began to move the muscles inside her ass. It felt like she had a milking machine inside her, but she wasn’t even moving on the outside. I let out a moan involuntarily. Then she exclaimed, “Now I’m going to finish you off, Sweetie. Hold on.”
She shifted her pelvis forward while contracting herself inside. I had no control; I shot my load like never before while letting out one long groan. She continued flexing her anal muscles on my now sensitive cock. I always thought of cross-dressers as submissive, but not Tiffany. She was surely in charge of this sexual episode.
Finally, she eased up and sat there smiling. Her eyes never stopped looking into mine the entire time. She tightened her muscles one last time as she lifted her body off of me. I could see my cock pulling out of her ass and the condom. I told her, “Tif, the condom came off in your ass.”
She said, “I know, Sweetie. It isn’t going anywhere.” She climbed off of me onto the floor. Pulling up her panties, she leaned over and licked the cum off of my dick before putting her face inches from mine and asked, “Would you like a little taste of your cum? It’s not a requirement and I understand if you don’t want to try it at this time.”
I guess I took too long to think it over and answer. She put her lips against my lips and slowly pushed her tongue into my mouth. I could taste and feel the unfamiliar substance on my tongue. It didn’t seem too bad. She French kissed me for a few minutes spreading the taste of my cum throughout my mouth. When she stopped, she said,”Good gurls like cum, and men like good gurls.” She pulled my panties back up over my softened cock.
I sat up on the bed. Tif sat down next to me. “I have a confession to make,” she began. “I really needed you in my ass tonight. It’s been a long time. I moved here this past summer from the East Coast. It is much different here than there. I had bookstores, gay clubs, CD meeting places, and so many other opportunities to meet men interested in gurls like me. It is much different here and I have been longing for intimacy with a man. I hope you don’t mind I took advantage of the situation.”
I answered, “Of course not. I’m just surprised that you could be uncomfortable anywhere. We are BFFs, aren’t we?"
“Yes, you’re right, we are. I think this is the beginning of a wonderful relationship. When can we get together, again? I can’t wait to spend time dressing you up and teaching you to be a gurl.”
I immediately said, “Is Friday night good?”
“It’s perfect. Could you do me a favor before you leave?”
“Just name it.”
She turned around, pulled her panties down below her cheeks, bent over and asked, “Could you pull that condom out, Sweetie?”
I grabbed the end that was hanging out and pulled it free from her beautiful ass. She pulled her panties back up, took the condom, and walked to the toilet, throwing it in. When she came back out, she pulled the first pair of panties that I picked out in the store from the bag and handed them to me. “Here, put these on for the ride home.”
I wiggled the panties down I had on, letting them drop to the floor. Then, I pulled on the sexy pair from the store. They fit so perfectly and felt so good. Tiffany helped me put my pants on and pulled my shirt on over the bra.
“I have a few gifts for you to take home tonight, Sweetie.” She went in to her closet and sorted through some drawers. Then, she brought me a pair of breast forms which she reached under my shirt and tucked into my bra. “How do you like them?”
“I love them, Tif.”
“Good, because I want you to wear them home tonight. I have another gift for you.”
She handed me a box with a see-through lid. There was a vibrator in it. She smiled at me and said, “You need to start using this now. You do want to be a real gurl, don’t you?”
“Yes, I do. I’ll use it tonight. Thank you so much.”
I gave her a kiss and a hug. She put the vibrator in the shopping bag with all of the panties we picked out tonight. Then she went to her closet and picked out a beautiful silk nightie, placing it in the bag, also. “You can wear this tonight. It’ll help get you in the mood.”
We both hugged each other. I put on my shoes, finished my drink, and took the bag as she walked me to the front door. I couldn’t believe that I was walking out the door with a bra on underneath my shirt. It was quite the thrill. This was only the first of many thrills yet to come from my new BFF. More to come.
