The light shining in the window woke me up. It took me a minute to realize I was in Tiffany’s bed and started to remember and replay the previous night in my mind. Her right arm was hanging over me as she spooned me. I could feel her perky breasts against my back. My cock was sticking out of the crotchless panties I was wearing. The lace was stiff from the dried cum all over. I still had a wig on, but it was out of place from sleeping with it on. I didn’t want to wake Tiffany, so I lay still for a little while.
When she finally stirred, she said, “Good morning, sunshine. How did you sleep?”
I answered, “Like a baby, girlfriend. Last night was so wonderful. You’re the best.”
“Does that mean you’ll stay the weekend?”
I quickly thought of what I might have to do since I only planned on being here last night. Then I thought to myself, what could be better or more important than this. I replied, “Yes, of course I will. But I must go home Sunday night so I can log on for work on time Monday morning.”
She assured me, “No problem, Sweetie. We can have breakfast, get cleaned up, dressed up, and go out for the day. It will be so much fun. How about a little sixty-nine to get the day started?”
In her usual self, she didn’t wait for an answer. She sat up, rolled over on top of me, moving herself down my body until her mouth was on my cock. This placed her cock, hanging out of her crotchless panties, over top of my face as I now lay on my back. I could feel the warmth of her mouth as she pushed her lips over my soft cock. I reciprocated by opening my mouth, raising my head slightly, and taking her already hard cock between my lips.
Although this was the second time her cock was in my mouth, it was the first time I was actually giving a blow job in my life. I wrapped my arms around her waist, pulling her down on me. The tip of her cock was at the back of my mouth, pushing at the entrance to my throat. I wanted to take more of it, but I wasn’t sure if or how I could. There was something magical about having her cock in my mouth, almost the same as having it in my ass; I couldn’t get enough. I wanted more of it.
At the same time, she had most of my dick in her mouth. Her lips were moving up and down my shaft. When it seemed like she was all the way down on me, she would push a little harder and I could feel myself entering her throat. Her lessons on observing women began to take over. I started to copy her movements. I used my arms to pull her into my mouth. This time when she was at the entrance to my throat I squeezed my arms around her as tight as I could while I tilted my head back. Without warning, her cock pushed into my throat. There was an instant feeling of accomplishment. I didn’t know it was possible to enjoy oral sex from this side. The intimacy was amazing. I felt joined to her.
Suddenly, I realized I couldn’t breathe. I pushed her out of my mouth in a panic as I gasped for air. It took a few moments to regain my composure. My mind went back to the feeling in my own cock as I felt how hard and wet I had become. I wanted to give her the same feeling she was giving me. Once, again, I pulled her cock into my mouth as I prepared to take her in my throat. This time she seemed more wet and slippery. This time I knew what to expect. This time I took a deep breath before I pulled her cock into my throat. It slipped in much easier than the first time.
I moved my head up a little taking it down my throat until her balls were smothering my nose before bobbing a few short strokes, then I shifted my head back, releasing her from my throat while still keeping her in my mouth so I could take a breath. I could feel my own cock being pulled into her throat during this breath break. It felt so good. I waited until she let up before I took her back down into my throat. We were like a see-saw as one cock went down a throat and the other came up. She was becoming more wet and slippery with each cycle. We both grunted back and forth at each other with our full mouths. Both of us had our arms wrapped around each other’s waist to pull ourselves into the other. It was an amazing experience as we satisfied each other simultaneously. The tension kept rising beyond what I thought possible. I wanted to hold back to make sure Tiffany came around the same time as myself, but I was ready to explode.
My grunts were becoming higher pitched. She began to almost whimper. Her grip on me tightened as her legs tensed up. I took a deep breath and held her in my throat as she did the same. I could feel her balls pulse against my nose followed by her cock pulsing in my throat as she began to pump her cum directly into my stomach. I became so excited that I exploded into her throat seconds later with such intensity that I could feel my own balls recoil.
I could feel the tension relax in both of our bodies almost immediately. I pulled back a little so I could breathe while keeping most of her cock in my mouth. While I knew she came, I really couldn’t taste it like I did last night. I felt so content lying there with her cock in my mouth as it began to soften a little. Softly, I sighed out, “Mmmm.” She responded with the same.
After several minutes, we had both softened, almost shriveling. I slowly pulled my lips from her cock. She lifted herself up, letting my cock slip from her mouth. Then she turned around, lying next to me, and gave me a huge kiss on my lips. “That was awesome, Sweetie. What a way to start the day.”
We got out of bed and took a shower together before I dressed in the new jeans, blouse, and bra we bought last night at the store along with a lacy thong from her dresser and breast forms. Then, she sat me down in front of the vanity and showed me how to make up my face with the new cosmetics we purchased. Finally, she finished with another wig from her closet while saying, “You should let your hair grow out. It’s a lot better than wearing a wig, you know.”
After changing the sheets, cleaning up, and eating breakfast, we decided to go to the park for a while. Tif said it would be a good opportunity to go out in public to practice walking and, maybe talking, with minimal risk. This time we took my car and I drove. She was right; I was comfortable at the park. We walked for quite a while. I was wearing flat shoes and increased my confidence and look in walking. We said hello to a few people we passed on the walking path. I was so excited being out in public in the middle of the day. Once we even passed two young men who turned and looked at us. I thought I was going to melt.
“Well, are you feeling more comfortable?”
I answered, “Yes, I am. I can’t thank you enough.”
Tif responded, “Good, let’s step it up another notch. We’ll go to a bar tonight wearing dresses.”
Damn, I thought to myself, every time I reach a comfort level, she takes me out of it. I have known her less than a week and she has changed my entire life. Although, I had to admit, it has been the best week of my life and I was probably heading in the same direction anyway. I’m sure it would have taken me ten years to get this far on my own. I took her hand and gave her a big smile.
When we got back to her apartment, we went to her walk-in closet and she picked out a skirt and blouse for herself. She said it would be a good chance for me to wear the skirt we bought at the store the night before. We both stripped down to our bra and panties as she asked me if I wanted to wear stockings tonight. I replied to her, “I don’t know. I’ve never worn stockings. What do you think?”
“Well, you have beautiful legs, but they are quite pale. Let’s get you a pair of thigh highs. They’re easier for going to the bathroom and they feel sexy. I know you’ll like them.”
As always, she was right. I loved the way they felt on my legs. She handed me my blouse as she said, “You have to button it yourself this time, Sweetie.” She put on her stockings, skirt, and blouse while I was still buttoning the left-sided buttons. “You’ll get better at it over time,” she chuckled.
When I finally finished with the buttons, she held my skirt out so I could step into it. She pulled it up, tucking in the blouse under the elastic band. It was such a thrill. I felt so exposed. There would be no hesitation stepping outside tonight. We both sat down at the vanity.
Tif said, “You have to keep working on your make-up. It is important for women and critical for us gurls.” We spent almost an hour as she showed me, again, step by step. She had me brush my wig while it was on so I could learn how to touch it up when we were out. Then, she went to her big jewelry box and picked out two bracelets, an ankle bracelet, and a cute little necklace. “We must get your ears pierced soon, Sweetie. How about tomorrow? It’s quick and almost painless.”
I replied, “We can talk about it in the morning.”
“Okay,” she said. “Are you ready for shoes?”
She went into the closet and came back with heels. I was hoping they wouldn’t fit, but they did. They looked good as I stood up, but it was clear that I would be practicing walking all over again. Tif advised me, “Walk like you’re standing on your toes.”
I walked around her apartment while she was getting herself ready. While the heels felt feminine, they were surely a challenge to master. Tiffany yelled out to me, “The sound of your heels are as important as the look of your walk, dear. It can be a dead giveaway.” She’s never short on advice, I thought to myself, but I quickly understood as I now paid attention to the clacking they made.
As I continued to nervously walk around the kitchen, I heard Tiffany walking in. She not only looked sexy in heels, she sounded sexy in heels. “Calm down, Sweetie. You’re going to be fine. Let me pour you a small scotch. Have I let you down yet?”
I smiled, walked over, and gave her a big hug. “No, you haven’t let me down. I’m so thankful to have you as my BFF.”
As we sat and finished our drinks, Tif said, “We need to find a name for you. I can’t very well call you Shawn when we’re out tonight. Do you have any choices?”
I thought about it for a few minutes, running a list of girls' names in my mind, before suggesting, “How about Katrina?”
Tiffany responded, “I like that. It’s a pretty name, Sweetie.”
I had to ask, “By the way, Tif, what is your real name?”
She answered with an embarrassed expression, “Thomas.”
We both laughed. I didn’t say any more.
Tiffany picked out two pocketbooks from her closet. She put the small purse with my license and credit card in one of the pocketbooks along with lipstick, make-up, a hair brush, and a mirror. Then, she put some things that I couldn’t see in hers. She locked up and we walked out to her car as I continued to work on my walk with heels. “Don’t forget you're wearing a skirt, Sweetie. Get in the car like a lady.” I had to think about that a little. So I watched Tif and followed her lead. I pulled my hands under my skirt and sat sideways in the seat. Then I swiveled around, keeping my legs closed. Another gurl lesson learned.
We stopped at a convenience store and got some cash from the ATM machine since we could have trouble using our credit cards in person. She said she knew an LGBT bar about thirty minutes away. It seemed like a nice place when we pulled in. We sat down at a table and ordered drinks and a large sampler appetizer as we had yet to eat anything since breakfast. There was a large walk-around bar across the room, a dance floor in the middle with a stage at one end, and high tables on the side we were sitting. There were subtle hints of its LGBT theme all over.
Tiffany said, “Bar food is my downfall. I love it in spite of it being bad for me and my weight. We may have to dance some of it off when the band comes on, later.” It seemed so natural and comfortable having dinner and drinks, as we enjoyed the evening. I almost forgot I wasn’t actually a woman.
Tif stood up as she said, “Let’s go freshen up, Sweetie.” I’ve heard women say that a hundred times, but never really understood it. “Don’t forget your purse,” she reminded me, another habit to be learned. I grabbed my purse and followed slightly behind her, studying her walk carefully.
We walked into the ladies' room, where there were two couples at the sinks looking into the mirrors. I wondered if this was normal or because it was an LGBT bar. Tiffany stepped into one of the stalls. I took her cue and stepped into another. Her timing was good. I really did have to take a pee. I pulled my thong down and my skirt up before sitting on the toilet. The thigh highs were a good idea. It was as easy and convenient as standing up and taking a leak, but much more sexy. I never thought I could get excited taking a pee.
Tiffany yelled from her stall, “How we doing, girlfriend?”
I knew it was in my best interest to respond. “Great,” I replied in a subdued, yet high-pitched voice.
When we were both out of our stalls, she took my hand and led me to the sink. We washed our hands and then she touched up her hair and then mine. I felt like she was my mother before sending me off to school as she examined my face and clothing. There was another couple doing the same thing next to us. One of them commented to Tif, “I love your shoes, dear. They go well with your dress.”
Tif replied, “Thank you. It’s hard to believe I only paid twenty dollars for them.” Everyone smiled.
When we returned to our table, the waitress was removing our plates and asked if we wanted another drink. Tiffany ordered two more for us. The band was setting up on the stage. I was getting a little nervous at the thought of trying to dance in high heels. I wasn’t much of a dancer in the first place.
The bar was filling up and it was becoming more apparent that it was a “friendly” bar. There were pairs of men and women everywhere. They were all busy with each other, restoring my comfort level as we seemed to blend in with the entire crowd. Once the band started playing, the dance floor quickly filled.
Tiffany took my hand and led me to the floor to dance to a few faster songs. The high heels actually seemed to help since they limited my foot movement, increasing my body movement. I carefully watched the other women dancing. As I began to copy their motions, I began to feel like I was becoming them. I would adjust my skirt and hair regularly. As they smiled at me, I smiled at them. I never thought I would enjoy dancing.
When the band switched to a slow dance, we walked back to our table. There were two fresh drinks waiting. The waitress told us that two men at the bar bought them for us and pointed them out. Tiffany told her to tell them thank you and invite them to join us if they would like. When I gave her a shocked look, she said, “Relax, Sweetie. It’ll be okay. There’s no harm in talking.”
A few minutes later, the two young men came to our table. One started the conversation, “Hello, ladies. How are you tonight? I’m Jimmy and this is Ted.”
Tiffany replied, “We’re good. Thank you for the drinks. I’m Tiffany and this is Kat, short for Katrina. Are you two gay?”
I looked at her and said, “I can’t believe you asked them that.”
Jim jumped in, “That’s okay. It’s a fair question. This is a gay and lesbian bar. I have to say we’re both bi. We swing both ways. Now, it’s my turn. Are you ladies lesbians?”
Tiffany quickly responded, “Touché. I guess you would have to say we’re T-gurls.”
As I stood in total shock, Ted answered, “Wow! I’d have never guessed. You’re both stunning and convincing women. It’s my pleasure to meet you.” He took my hand and held it to his lips, giving it a little kiss. Then, he did the same with Tiffany.
Jim did the same before saying, “I couldn’t agree with you more, Ted. Ladies, you are both beautiful and I so appreciate your honesty. Now that we have cleared the air, would you care to dance?” He held his hand out to Tiffany. She took his hand as they both looked at me. I guess I, also, now appreciated Tiffany’s honesty. Once again, she took an awkward experience and made it quite comfortable. I smiled and held my hand out to Ted.
We all walked out to the dance floor. The band was still playing slow dance music. Ted put his hands on my waist and I put my hands on his shoulders. He looked into my eyes and said, “You are amazing. How long have you been transitioning?”
I replied, “Almost a week.”
He laughed, “Seriously. I’ve known a lot of cross-dressers, T-gurls, and trannies. None of them could hold a candle to you, Kat. How long has it really been?”
I didn’t answer. I just held him tighter. He responded by moving his hands around to the back of my waist. My appreciation for Tiffany was never greater than at this moment. She was really the amazing one and truly my BFF. I couldn’t believe how far she brought me in less than a week. Ted leaned his head in and gave me a few little kisses on my neck as we continued to slow dance. Then, the band raised the tempo. We danced to a few of the faster dances before returning to our table for our drinks.
The four of us spent the next few hours talking, drinking, and dancing until the band packed up for the night. At one point, Jim asked us if they would see us again. Tiffany said we would answer that after we freshened up. She reached for my hand and we headed to the ladies' room.
After we finished peeing and washing our hands, Tiffany asked, “Well, what do you think? Should we give them our phone numbers? I really like Jim. Or would you like to go all the way and offer to spend the night with them?”
I was as excited as she was. I couldn’t believe I answered, “Let’s go all the way. Ted is such a gentleman. I know it’ll be great. We should suggest their place though, don’t you think?”
Tiffany agreed. We went back to the table and gave them our answer. Jimmy said we could go to his apartment. Ted took my hands in his, then gave me a little kiss on the lips, and said, “We can ride in my car. Tif and Jim can ride in her car.” We finished our drinks and went to the cars. Ted opened the car door for me. I remembered to get into the car like a lady. Ted smiled as he watched me. I really felt like a lady when I was acting like a lady. The thrill of wearing a skirt in front of a man was such a rush.
It was a short ride to Jim’s apartment. Ted got out, ran around the car, and opened the door for me, again. As I swung my legs out and put my feet on the ground, he put out his hand to help me. I stood up, turned around, and bent over to get my pocketbook from the car seat. He placed one hand on my waist. As I stood back up, I placed my hand on top of his, pushing it down onto my one cheek. Then, I turned around, facing him. He leaned in and kissed me on my lips. I responded by wrapping my arms around his shoulders and wagged his invading tongue with mine. Never before had I kissed a real man. The passion was unbelievable.
A voice rang out, “Get a room.” Tiffany and Jimmy were walking past us toward the front door.
Ted chuckled a response, “Can I use your room, Jim?”
Ted took my hand in his and we followed Jim and Tif to the apartment. Once inside, we took off our high heels and Jim poured us all a drink. Tiffany asked where the bathroom was before instructing me to “help her freshen up.” I was getting ready to tell her we just freshened up before leaving the bar, but then I thought to myself, she always has a reason for her actions. I should trust my BFF, so I smiled and went with her to the bathroom.
She closed the door behind us. “You must be my good luck charm, Sweetie. I’ve gone to that club since I moved here and this is the first time I met a man, let alone went home with one.” She reached into her pocketbook, pulled out two packets, and handed them to me. “Here, these are lubricated ribbed condoms. I think you’re going to need at least one. Don’t let him near your ass without one on. If you have any trouble with him, yell for me. Take one of these, too.” She handed me a small pepper spray.
I said, “Thank you, Tif. I don’t think we’re going to have any problems. They both seem so sweet.”
She replied, “I’m sorry, but I’m your BFF. I’m always prepared for anything and I want you to be, too. I hope I didn’t scare you out of having a good time tonight.”
I gave her a big hug and told her, “You’re the best. Now let’s get laid, Sweetie.” She fussed with my hair a little and then gave me a pat on the ass as we walked back to the kitchen with the guys.
Tif picked up her drink, took a sip, and told Jim, “Lead me to the bedroom, stud.”
They walked down the hallway while Ted handed me my glass. I turned and leaned against the small island counter as I took a sip of my drink. Ted stood behind me. He pulled my hair back a little, exposing my neck, giving me several small kisses, sending chills through my body. I let out a very quiet moan. He moved his hands over my shoulders, then down my back. I moved back from the counter half a step, keeping my hands on the counter.
He moved his hands down to my waist. I shuddered as his hands reached around to the front of me and worked their way up to my breasts. I leaned my head back toward his shoulder behind me. Again, he gave me little kisses along my neck. It was a sweet seduction. It was at this moment I became a woman and knew that feeling was not going to change. I raised my right arm and placed my hand on his head. He tightened his embrace and moved his lips to the side of mine. Although I was wearing breast forms, I could feel his hands against them. Another moan escaped me. I pushed my ass hard against his groin.
He moved his lips along my face, down the side of my neck, returning to the back of my neck once again. His hands drifted slowly from my breasts to my waist. I put my hand back down on the counter and used them both to hold me up, half bent over, grinding my ass against him. He backed up slightly and lifted my skirt, rubbing his hands along my exposed cheeks. My skin was tingling from the feel.
I reached over to my purse, pulled out one of the wrapped condoms, and handed it back to him. I could hear him unzip his pants, then I could hear the wrapper being torn open. It was music to my ears. I wasn’t sure what to expect since I never saw or felt his cock yet. He pulled the back of my thong down before rubbing the tip of his dick up and down my ass crack. It felt quite large.
I held onto the edge of the counter as he started to lean forward. My cheeks separated from the tip of his dick pushing into them as he used his hand to guide his shaft to my waiting entrance. He pushed a little, but his cock began to bend. He pulled back slightly and poked forward a little. Just when it felt like he was going to penetrate me, he backed off a little before poking forward again. He repeated this several times as he said, “Damn, Kat, you are really tight. I’m not hurting you, am I?”
“I’m okay, Sweetie. Don’t you like it tight?”
“Oh yes, of course I do,” he said as he pushed a few more times, going a little further each time as my anal ring started to dilate. Then, using both of his hands to hold his cock, he gave a steady push forward. My sphincter finally yielded to him and I could feel the textured condom sliding through my anal ring as it began to fill my colon. I don’t think there’s a better feeling in the world than anal penetration. At least, for me anyway. My own cock was becoming hard and oozing precum into the front of my thong.
Ted’s cock was bigger than Tiffany’s, but not as stiff and hard. It was all good, from entry to complete penetration. I felt so fulfilled as his balls pressed against mine when he couldn’t push in any further. I could have stayed frozen in that state forever. His hands tightly gripped my hips as he began to move back and forth fucking my ass. He started to grunt a little and I began cooing like a dove. I pushed my ass back into him, meeting his thrusts forward, my hands still holding on to the edge of the counter.
This felt so much different than with Tiffany. Her cock slid in and out of me when she was fucking me. Ted seemed to move in and out of his large soft outer shaft, resulting in less friction on my colon walls, a little like a vibrator. But, I felt a cushioned blow on each thrust forward that sent shock waves through my body. My colon was tingling and I could feel occasional spasms deep in my ass. Ted would thrust in and out short and fast for a dozen strokes, then switch to long slow strokes.
We must have fucked like that for a long time as I heard a voice in the background, “Wow, Kat, you look so hot getting it up the ass.” It was Tiffany. She just stood there smiling and watching us. I couldn’t believe how much I had changed in a week. I never thought I would be getting fucked in the ass in the middle of someone’s kitchen while being watched by someone.
A second voice chimed in, “Wow, you’re right, Tif, that is so hot. That’s almost as hot as you were, sitting on my cock like a cowgirl. How long have you two been going at it?”
Neither Ted nor I answered as Ted kept up his pace. I just smiled at Tiffany. She sat down on one of the stools as she said, “You better make yourself comfortable, Jimmy. I think they might be a while.”
Ted picked up his pace. I couldn’t hold back my little moans as he continued to send waves through my body. He was still grunting, only louder. We became oblivious to our two spectators as our lust increased along with the heat. My thong was soaked with precum. Ted was using his thumbs to spread my cheeks apart to get deeper inside me while his hands were holding my hips on the side. The spasms were increasing in my colon. My anal ring responded by tightening with each spasm on Ted’s cock.
His reaction was immediate. He yelled out loud, “Oh… Oh… Oh shit! Your ass is sucking my dick. I’m gonna cum any minute now.”
I was hoping he would cum first, but I couldn’t hold it any longer. My cock filled the front of my thong with cum as my colon went into an unbelievable spasm. I let out a high-pitched moan that was just short of a scream. Tiffany looked at me, her mouth and eyes both wide open. I felt like I swallowed a live electrical cord. I was tingling everywhere inside.
My throbbing sphincter must have been too much for Ted. He gripped my hips hard, leaned forward, pushing me up on the counter before making several loud groans, almost as if in pain, tensing up and suddenly freezing. I could feel his cock pulsing inside me.
Tiffany broke into a wide smile as she said, “That was two awesome orgasms!”
My colon started to relax as Ted began to soften in my ass. His grip on my hips began to ease up. I didn’t realize it, but I was standing on my toes, partially suspended from Ted pushing me up on the counter. He must have been standing on his toes, too, as my body lowered a little as he declared, “That was the most intense orgasm of my life. You’re incredible, Kat.”
I was so disappointed as he pulled his cock from inside me, leaving me with such an empty feeling. He pulled my thong back up in the back. I reached for a paper napkin on the counter, turned, and wrapped it around the condom, pulling it off him. It was full and dripping with his cum. I knelt down and licked the cum from his cock. It was almost sweet tasting. When I stood back up I could feel my own cum dripping in my thong and down the front of my leg. I excused myself to ‘freshen up’.
Tiffany followed me into the bathroom as I told her I was a mess. She replied, “Doesn’t it feel good, though?” As I pulled my skirt up, she pulled my thong down before kneeling and licking my cock clean. “We don’t want to waste this. You worked so hard for it. You were awesome, Sweetie.” She took a washcloth from the towel rack, wet it, and then wiped my groin area and legs. “Step out of your thong, it’s a mess. You don’t need to wear it home.” She put it in her pocketbook as she smiled at me.
My last thrill of the night was walking out of the bathroom with no panties on under my skirt. Oh, how I love being a woman. We went back into the kitchen to put our shoes on and say goodnight to the guys. After exchanging kisses amongst us, we gave them our phone numbers, before leaving to go back to Tiffany’s apartment.
I still can’t believe how lucky I was to find such a great BFF. I knew we would be having many more adventures together as she continued to teach me how to be a woman.
