A Woman on the Weekend

~So what started as a one-shot, primer story has become a trilogy! Unless I think of more to do with the story without it getting too stale, this will probably be the last part. Plus, I want to write something with a happy ending. I recommend reading "A Weekend of Firsts" and "A Halloween Weekend" if you haven't already before reading this one!~

*****

Sending...

I sat there looking at the phone for what felt like hours with the message still not going through. It was just staring right at me, torturing me. Almost any way this situation could end played through my mind while waiting on this message to go through. Would she be happy, or accepting like Phil was? Would she reject me in disgust? Would she not even answer or ever talk to me again?

Failed. Message not sent.

Well, that wasn't an outcome I planned for... I sat there for a moment while the phone asked me if I wanted to retry sending the message. The failure to send the text gave me an idea. If I wanted Rose to find out my secret, I had to do it on my terms, and I had to do it in person. If she saw me, and saw I was happier this way, maybe she wouldn't reject me and she would react like Philip did. It had to be the best way. It had obviously worked the first time, so it should work again, right?

Me: (Let me see if I can arrange a meeting with her for you this weekend. Sound cool?)

Message sent.

Rose: (...)

Rose: (Sure! Friday night is fine with me if it is with her. Dinner maybe? Are you going to come too?)

Me: (I might have plans this weekend, but if I can I will. If not, I'll let you two have a girls' night.)

Me: (Is it okay if I ask why you've taken such an interest in her?)

Rose: (Well, she seems pretty cool, and I don't really get along with most girls our age. It would be nice to make a new friend. I had this instant connection with her I think, and I want to see if she feels the same.)

Me: (Okay. She said Friday is fine.)

Rose: (Yay!! I can't wait.)

I had a few days to prepare. I texted Philip about what was going on and told him I wanted to go in person on Friday, so I would have to postpone our weekend activities.

Philip: (Well, I know it's not a weekend, but tonight is Halloween. Since we have to start late this weekend, care to make it up tonight?)

I replied immediately with a yes. The thought of being with Phil tonight was so strong, that I didn't even care it was a weekday. Idea! It's Halloween. I can totally walk out in the open dressed as Tiffany and pass it off as a costume! I thought Harley might be a little too much, so I just got right into my process of getting ready and all femme'd up. I left my room and went across the hall into my sister's room to pick out something to wear. I had just shaved again on Sunday, so I didn't worry about re-shaving my legs or anything. I pulled a pair of lacy, red panties from her top drawer and a matching red demi-bra. I hooked the bra in the front at first, and then spun it around so the cups were in front before sliding the straps up my arms, to my shoulders. I slowly pulled the panties up my legs and firmly tucked my cockette in place.

I almost sprinted over to Tam's closet to sort through my outfit options for tonight. I finally settled on a slightly lower cut blue top with a frilly collar and a black pencil skirt. After I had my outfit done, I pulled my homemade falsies out and stuffed them into the bra. After a little bit of re-arranging, I managed to get some convincing looking cleavage. Thank you XXY chromosomes for the extra breast tissue! I pulled the curly blonde wig out next and fixed it to my head before sitting at her dresser to brush it out and apply my makeup. I went for a natural cute look tonight, since I was going out "normally". In our weekend escapades, I had done a little more shopping out of town, so I grabbed a pair of strappy, black stilettos from the mall a few towns over. I buckled them on and headed out to meet Phil.

On the way out, I passed the living room and made a really bold move. I called out to my parents to let them know I was leaving.

"I'm heading out to Phil's for a costume party. " Crap. That was my femme voice. I lowered my tone and added on "I'll be back later."

Oh! Umm... nice costume?" My mom answered back looking me over head to toe. I could hear a slight snicker from my Dad behind her.

"Oh. Yeah. I kinda lost a bet. Phil caught the bigger fish so I had to dress as a girl for Halloween."

"Oh. Okay then... Be safe."

"I will, Mom." I headed out to my car, heels clacking on the pavement as I moved to my car. Mom followed my every step with her eyes as I went. I'm glad I got used to walking in heels. I'd have been so embarrassed if I fell over and needed rescuing. I drove to Phil's house still feeling my heart pounding as I went.

When I got up to his door and rang the doorbell, Philip's dad answered.

"Uh, can I help you miss?"

"I'm here to see Philip. Did he say I was coming?"

"No. He said a friend was coming. I thought he meant... some one else. He really only has one friend I know of." It took me a second to realize he meant me. Well, he meant Tim me.

"Oh. Sorry, sir. It's me, Tim. This is my Halloween costume. Lost a bet." His jaw dropped along with the tone of my voice as he turned around and called Phil.

"Phil! Tim's here! What kind of bet did you make with the poor guy?" He turned his attention to me again. "For doing this on a bet, you look really convincing. Sorry I didn't recognize ya there. It's just you look really -" He was cut off by Phil coming downstairs looking wide-eyed at the door.

"Uh, hey Tiff- uh Tim. I wasn't expecting you to be in, uh, costume yet. You look nice."

"Thanks," I smiled back to him, "not bad for a quick job right? I mean, I hope you didn't think I didn't take our bet seriously." I was really hoping he would catch on and play along.

"Oh, right! The bet. Yeah. Haha. You totally look like a chick. I knew it!" He hurried past his Dad and went to his car. He opened the passenger door for me as I walked over gracefully and sat in the seat, smoothing my skirt as I sat. He ran around and got in the driver seat as we took off.

"Are you crazy? Walking up to the house like that? I mean, I thought you wanted to keep it a secret?"

"I did, well I do. I think. But I thought since it was Halloween, I could pretend Tiffany is just a costume. For a day, I just get to be out in the open. No secrets or lies. It feels really nice."

"Okay, okay. I get that. So where to then, Tiff?"

I smiled and moved my hand across the console to his crotch and began massaging his semi-hard cock through his jeans, "Anywhere. I just want to be with you." Just then, my phone went off.

Mom: (You're father and I are going out dancing and to get some drinks. We'll be out late, so don't wait up. Btw, I hope Phil likes your costume. Looks like you worked pretty hard.)

I read the message to Phil and we changed course and headed right back to my house. We were barely in the door before we were all over each other. I had him locked in a tight embrace kissing him passionately as our tongues explored each other and met continuously. We went straight for the living room, not even bothering to turn on the light. A movie was playing on the TV, but we didn't care. Phil sat down on the couch and hurried to unbutton his pants. He slid them down as I knelt in front of him on both knees, my heels tucked under me. I grabbed his boxers and pulled as he shimmied out of them. No sooner were they off than my hand was around his still enlarging cock. I leaned forward and kissed the head. I looked up into his eyes as I opened my mouth and let his member slide past my red lips into my waiting mouth. I touched the tip with my tongue as I began bobbing my head up and down. The irony was not lost on me that usually people were bobbing for apples on Halloween, but not me. I was bobbing for cock and I loved it. My gaze never left Phil's as I kept swirling my tongue around his shaft as he pushed and slid further into my mouth. It was getting harder to take as he was quickly hardening to his full 9.5 inches. I struggled to control my gag reflex as I felt the head hit the back of my throat. He slid out and back in again until we got into rhythm. With each stroke towards my face, my nose was closer and closer to his groin. It was turning into a full on deepthroat session. I had just realized this was another first. I've sucked his cock before over the last few weeks, sure, but this was the first time I ever had him this deep. I could feel the tip of his cock pressing against my tonsils on each push. After deepthroating him for almost 20 minutes straight, I backed up and pulled my head away, letting his erect cock fall from my mouth.

"I wanna go for a ride now, baby. Wanna drive?"

"I hope you like stick shift." I giggled at his corny joke as I wiggled out of my panties and let them fall to the floor. I centered myself over him and swung my legs over his lap. I hiked up my skirt and slowly began lowering myself onto his waiting cock. He guided his bare member into my ass as I grabbed onto his shoulders for leverage. I was still loose enough from our weekend sexcapade that I could feel his cock quickly fill me up as I hit his lap. He grabbed my sides just above my hips and lifted me up off his lap and lowered me back down slowly. I moved my hands from his shoulders and wrapped them around the back of his neck as he lifted me again. I kissed him passionately as he slammed me back down to his lap with gusto. Up. Down. Up. Down. He started picking up the pace until I was bouncing so quickly on his cock feeling his bare flesh slide in and out of my hole. The pace picked up and I could hear the sound of ass slapping against his groin over and over. We were so into our intense riding and make-out session, we never heard the door open. We barely even came to our senses as the lights turned on and I heard my mother gasp.

"I KNEW IT! I knew you were walking to well in those damn heels, but this!? I come home and find my son pegged on the dick of his best friend, riding him like some damn cowgirl? Halloween costume my ass!"

I turned and saw my parents, standing in the doorway to the living room, my Dad's head was turned away from us, but it looked like some sort of smile was on his face. They must have come home early for some reason. Mom was beet red, and it was her turn to face the other way as I stood up, while Phil's cock popped out of my ass. He quickly tried to pull his pants up as I grabbed my panties from the floor and ran past them into my room heels clicking rapidly on the hardwood floor as I entered my room and slammed the door.

Only minutes passed, but it felt like hours, while I could hear Philip ask my parents to please let him talk to me before he left. He knocked and slowly entered my room and sat down on my bed next to me. My knees were up against my forehead with my arms folded to hide from everything around me.

"Hey," he spoke softly. "I talked to your parents. They're not angry, you know? Your mom was just... um... surprised. Just as surprised as she would be if she walked in on Tam. Your dad didn't say much, but I think we need to go talk to them. Together."

I picked my head up and looked into his eyes. I saw nothing but concern, and truth. No doubt he was sincere. "Okay." I sniffled. "Let's go."

We spend the next few hours talking to my parents, and through a few teary moments, I told them how I had been dressing for years. I told them how nothing felt right until I was dressed. I told them how any girl I tried to be with just didn't click, and I told them we used "camping trips" as a cover story for our weekend adventures in motels towns over. My parents told me how they were shocked seeing it, but had suspected something for a while. They knew I wasn't happy. I was their kid, after all. It felt like ages before Dad said anything, but he had a sort of bright look in his eye. All he said was something that would resonate for a little while.

"I'm going to say this outright. It's been hard since your sister left. I mean, losing my little girl. I feel like we pushed her away. I won't make that mistake again. Someone up there just gave me a second chance at having a daughter." We all cried, and laughed. My parents excused themselves to their room, and I went to my own along with Phil.

"So what now?" He asked.

"Just, stay with me tonight. Please?"

"Okay. But first, I think we have some unfinished business?" I giggled and slid my panties off once again, tossing them to the floor. I unbuckled my stilettos and threw them aside before dropping my skirt. I took off my blouse, followed by my bra with the forms in it. For the first time, with the only exception being my wig, I was truly naked before Phil, showing my full trust, as he quickly stripped too and positioned himself over me, just like he did the first time we fucked. I spread my legs for him slowly as he glided into my still stretched hole. This time it was tender as he slid in and out. We weren't just fucking, or just having sex. He slowly pumped in and out of me, with force, but also with love. What was happening now hadn't occurred to me before. We were making love. This was the difference. Our trust was out in the open. Our love was out in the open. I looked up into his eyes and he looked down into mine, still pushing himself in and out of my ass.

"I love you." I said it first. And I truly meant it. I knew it was the truth.

'I love you, too." And he kissed me slowly, and passionately as we continued in perfect sync. Long strokes in and out, my ass moving to meet his groin at every push and pull. Our moans and grunts, along with saying each other's names a few times were louder than ever. Then, for the second time in less than a week, he stopped and pushed himself all the way into me. I locked my legs around him and held on tight as our bodies both began to twitch. I felt the spasm as he shot jet after jet inside of me. My whole body shook as my own cockette began spurting jets of the fluid out across my flattened stomach. Phil stayed on top of me and let his cock soften before pulling it out and rolling over on the bed, laying next to me. I snuggled closely against him and laid my head on his chest. He wrapped his arm around me tight and we fell asleep together, his head resting on top of mine. For the first time in a long time, I felt not only safe, but free as we drifted.

I woke up the next morning before Philip did. We were spooning and I could feel his morning wood pressed firmly against my ass. I slid out of bed and walked over to the floor. I picked up my bra and panties and put them back on, along with the forms. I couldn't be bothered to find my shirt and skirt to I just grabbed his shirt and put it on. it fell over me like a small dress. I heard movement in the kitchen and walked out to meet Mom, already up making coffee. I couldn't help but laugh because we matched. She wasn't wearing anything except Dad's shirt from the night before either. She turned around and laughed too.

"Long night?" She asked cheekily.

"You too?" We laughed and hugged as she offered me a cup of coffee. We sat and talked. Really talked for the first time. I didn't have anything to hide anymore. Nor did she. We sat at the table finally bonding in a way we never did as mother and son. We were bonding as mother and daughter. We talked about everything. We talked about how my school was going, we talked about work, and then we talked about boys. Of course we knew we both loved our partners and would never do anything to cheat on them, but we talked about what male celebrities we would sleep with. That's when Dad walked in to nonsensical giggling,

"Morning girl talk?" He asked with a grin as he leaned over and kissed Mom. "OH! In all the excitement last night, we never asked. What is our daughter's name? We can't very well call her Timmy."

"Tiffany. I really like the name."

"I coulda told ya that," said Mom, "I heard Phil saying it through the walls last night." I turned beet red and we all laughed. Phil walked in at that point wondering what was so funny, and where his shirt was.

***

The rest of the week was uneventful, but I did talk to the college and to my job about transitioning from Tim to Tiffany on campus and at work, and it went surprisingly well. Mom called an endocrinologist, and pending approval from my counselor, I would soon be taking hormones. I would take a few days off, getting a long weekend to get everything in order, but next Monday I started my new life. All I had to worry about today was getting ready to meet with Rose. She wanted to meet Tiffany, and it was time to tell her the truth, especially since Tim wasn't going to be around a few days later. I dressed casually, but still kind of cute. I went ahead and got my ears pierced, so I put in hoop earrings, and had a matching necklace and wrist bangles. I wore a black tank top with a long striped sweater over top, tight blue with a rip in the knee, and my boots from my Harley costume. I was carrying a black purse with all my essentials. I also picked up a new wig, this one the same shade of blonde as my curly one, but it was slightly longer and straight with a sideswept bang. I walked into the cafe we were meeting at just off the college campus and I saw her sitting in the corner booth. She waved and smiled brightly. I smiled and waved back as I walked over towards her. I sat down and started off.

"Hi, Rose. Good to see you!"

"You too, Tim. Sorry, Tiffany."

"You knew?"

"I had my suspicions." She said with a smile, "Seeing you here now, no clown makeup and mask, I would recognize you. I know you too well. Plus, you didn't hit 'no' when it asked if you wanted to retry sending a message."

She turned her phone around and showed me her messages. Surely enough, there was a message at the bottom that read two simple words.

Me: (She's me.)