A Weekend of Firsts

~The following is just a one-shot primer story that is based on true events, detailing my first time. I'm back!! Sorry for the absence, but I entered into a relationship with someone who wasn't fond of my writing. Won't make that mistake again! Here's a little primer story to get the (creative) juices flowing again!~

I had this whole weekend planned out for months. It was supposed to go all according to my master plan, but I guess it's in the nature of even the best laid plans to eventually be derailed. Everything either went horribly wrong. Or horribly right? Well, let me start at the beginning.

My parents were going out of town for the whole weekend. My mom won tickets to a cruise, so they decided to get their second honeymoon in. I was okay with it. It meant I would have the whole house to myself for the entire weekend! My brother moved out ages ago, and my sister eloped with her boyfriend somewhere in the next state over. I was finally going to have some much needed alone time.

I got my weekend in started off right. I ran a nice warm bath as I got my favorite Skintimat Shaving Cream and razors out of their hiding spot in my sister's old room. She left enough of her stuff in there, and we were close enough to the same size, that it was the perfect hiding spot for things I didn't want my parents to find. On the way home I bought the prettiest new lingerie I could afford, a light blue babydoll with black polka dots and bows, and a matching sheer black robe. It was barely long enough to cover anything, but it still looked divine. I also bought a whole pack of sheer lace panties, and bought matching bras in each color. I decided on the black tonight.

All I could think about was slipping into my new lingerie while I soaked in the tub and shaved my body clean of all hairs I could find. Pesky things. I've never been too fond of the hassle of swapping out of "boy mode", but I loved the results! I stepped out of the bath tub and toweled myself off slowly, taking time to caress my freshly shaven legs, arms, armpits, face, and of course my cock. Or cockette, I guess. It was hardly big enough to be called anything but. At a mere 4 inches with full hard on, if I was REALLY horny, I didn't think many girls would be too happy to see it.

What I was clearly lacking in masculine features, I made up for in feminine ones. Lucky me, I had Klinefelter Syndrome, which made my chromosomes XXY and gave me wide hips, a sunken waistline, almost no visible Adam's Apple, and sparse body hair. Others may have seen this as a bad thing for a strapping young man, but to me, having this intersex condition was a blessing in disguise. I never felt right as a boy, and even my body seemed to agree.

I wrapped myself in a towel and moved to my sister's room. I went into the back of her closet where I had an old shoe box hidden. I took everything into my room and started to get ready. To complete my look, I raided her make up table. I decided to go all out this weekend. I sat down in front of the vanity mirror on my own dresser and got to work. I dropped the towel and bent over to slowly pull the lace panties up my smooth legs. I firmly tucked my cockette in place and clasped the bra in the front before spinning it around to my back and pulling the straps up my shoulders. I reached into the box where my homemade breast forms were sitting. I filled two balloons with rice and then covered it with knee-high stockings that tied into a not and cut off the excess. The knots actually made cute little nipples. After stuffing them into the bra, I walked over to my bed where my new lingerie laid out ready.

After getting dressed and tying the belt of the sheer robe, I sat back down to the dresser and brushed my shortish hair straight back, placing a black wig cap over it. I had recently ordered a lace front wig for a "costume" but it was actually for my girl's weekend in. I placed the wig on my head and set it into place, letting the bouncy blonde curls fall over my shoulders. I then got to work on my face. I stood up and looked into the mirror. I didn't do half bad. Smiling back at me was a pretty blonde 19 year old with full looking C cup breasts. Granted, she looked a little lanky, standing at 5'9 and weighing in at only 110 lbs.

Now that my transformation into the girl I had named Tiffany was complete. It was time for her to enjoy herself. I had made another purchase a few weeks ago and hid it in my shoe box. It was time to test it out. I reached into the box and pulled out a bottle of silicone lube and a brand new 5 inch vibrator. It was realistically shaped, and had three settings. It was my first one, and I was finally ready to take the plunge, both figuratively and literally. I never had much luck with girls. Even when I tried to have sex the first time, it just didn't feel right. We broke up the next day. A few weeks later, I found myself purchasing this dildo at a sex shop a few towns over, just in case.

I pranced over to my bed, lube in one hand and vibrator in the other. I set them down on the towel I had laid out just in case things got messy. I opened the bottle and placed some lube on the pointer finger of my now gloved hand. It felt cold at first, but then slowly started warming up as my finger penetrated my virgin hole. I grabbed more lube, and slowly inserted the second finger into my waiting ass. I began stretching my hole as much as I could, adding my third finger in. Then the came the fourth. I began pushing my fingers in and out of my ass and the feeling was just indescribable. It was so much better pleasuring myself this way then it was with me trying to be the man with a female partner.

I laid down flat on my back and decided it was now or never. I grabbed the dildo, and poked the now stretched opening with the tip. I slowly pushed it in and gasped with a mix of pain and pleasure. The pain quickly subsided as I relaxed myself and allowed it to slide all the way in. I started to moan as I began sliding the dildo in and out of my ass. I was in heaven! This was what I was missing. I thought about how much fun this weekend was going to be, and then remembered it could get even better. I pushed the dildo all the way into my ass one last time and turned the knob. I felt the vibration from it over my whole body. It felt amazing. I turned it up once. I was letting out the most feminine sounds I had ever heard. I turned it up to the third and maximum setting. The buzzing got louder and faster as I felt my body begin to tremble.

It was sheer bliss. It was my first time masturbating as a woman and it was intense! Nothing could ruin this moment, I thought. And that's when I heard the door open.

"Yo, TIm! You in your room?". SHIT. It was my best friend Philip. I jumped up, pulling the still on vibrator out of my ass and threw it on the floor alongside the panties that had been pushed aside and soaked in pre-cum. I tried to shut and lock my door, but it was too late. I was standing on the inside of my doorway, looking up at Philip's face.

"Uh - I-, It's - I can explain." I stammered out the best that I could. I backed up from the door, and let Philip in, dropping my gaze. I didn't want to see the look of disgust on his face. It felt like an eternity before he spoke, over the still buzzing dildo on my floor by the bed.

"Well, when you told me your parents were leaving for the weekend, I thought you meant we were going to have a bro weekend. But this? This is..."

"This is... This is Tiffany. I'm sorry if you find it weird or if you think I'm a sick freak. Go ahead and leave if you want-" He shut me up my pressing his finger to my lips. He moved it down to my chin and pulled my gaze up to meet his. Even though I was barefoot he still felt like he was towering over me at his 6'1.

"Interesting. I was going to say interesting." He walked over the the dildo and picked it up. He turned it off and set it down on the dresser, stopping to look at the wet lace panties on the floor. "How long has this been going on?" He asked in a soft tone.

"A while. I've always felt different. I tried being 'normal' and it didn't work. You must hate me now."

"Tiffany, I could never hate you." It was weird hearing someone else call me that name for the first time. "I'm a little disappointed you didn't tell me. I thought we were closer than that." He sat down on my bed and I walked over and sat down beside him. He put his arm around me and pulled me into a hug.

"So, you aren't mad? You don't hate me? Or think I'm sick?"

"God, no. Your're still my best friend. Doesn't matter if you want to be a girl or not." He looked down at me and smiled. I looked up and smiled back. "That's better. You know, you're really pretty when you're smiling." I thanked him and looked over at the dildo on the dresser. Phil caught my gaze. "Um, sorry if I interrupted something. I can always come back tomorrow or-"

"No. I want you to stay. I'm sorry I thought you were gonna freak. I've just heard really bad stories and-" He interrupted me this time by leaning in to kiss me. My eyes widened in surprised but I quickly closed them and let myself fade into him. He broke the kiss and looked at me seemingly surprised I hadn't tried to fight it.

"I'm sorry if that was too direct, but you're just so beautiful and I thought you could use someone tell-"

"Shut up and kiss me again." It was my turn to interrupt him as I leaned up and locked my lips onto his. We broke only for a moment, for me to take of my robe and throw it to the floor, leaving me in only the blue babydoll. I melted back into him, our lips locked again. I threw my arms around his neck as he pulled me closer to him and put his hands at my waist. We fell sideways into my bed, still locked in a passionate embrace. I wasn't sure how far this would go, but I decided to try my luck. I tore one arm from his neck, sliding my hand down his chest, and finally into his pants. I wrapped my fingers around his cock and began stroking as I felt it stiffen at my touch. He rolled us over so I was now on my back, laying helplessly underneath him. Not that I wanted help any way. I unbuttoned his fly as he took his shirt off and threw it on the floor. I shimmied his pants off, followed by his boxers, and as he was positioned over top of me naked, I went back to stroking his cock.

I had this weekend all planned out, and now it was fully derailed. I liked where it was going though. And apparently, so did Phil. I could now get a look at his cock in it's magnificent glory. It was far bigger than my dildo. It had to be at least 9 to 9.5 inches long, and it was kind of thick. As I was pinned to my own bed underneath my now naked best friend my senses came to me as I realized I had now not only masturbated as a woman for the first time, I kissed a man for the first time, and gave my first handjob. I still was in the process of giving it. I knew what was coming next. I wanted it. I was about to experience a real cock for the first time, and it was going to be Phil's. My best friend was about to make a real woman out of me and I was ready for it. As if reading my mind he looked into my eyes and spoke for the first time since I kissed him.

"I think we know what's about to happen next, but I will only do this if you absolutely want to."

"I want to."

"You're sure? I don't know if there's any going back to normal if I fuck my best friend in the ass."

"We've already made out, and my hand is still on your cock, silly. I think we're past that point. I. want. this. I want you." He needed no further encouragement. He leaned over the bed and pulled a condom from his wallet. He told me he was always prepared just in case. I took my hand off his cock as he put the condom on. I reached over and grabbed my lube bottle. I was gonna need a bit extra for this. It's a good thing I had already stretched myself some, because my best friend was hung like a horse. He hovered above me and put his hands down on the bed my shoulders as I spread my legs open. He lowered himself onto me, as I guided his cock to my waiting hole. I felt the tip poke my entrance like the dildo had just a short while ago. He pushed his cock into me and I screamed out in my loudest most feminine sound yet. He stopped for a minute.

"Let me know if it hurts too much. You're so goddamn tight, Tiffany."

"Stop talking and fuck me, Philip." I whispered into his ear as I threw my arms back over his neck and wrapped my legs around his back, trying to push him further into me. He needed no further encouragement as I felt the full length of his cock fill me up. I thought this thing was big with my hand around it, it felt monstrous in my ass. He backed it out slowly, and then slowly pushed it back in. I let another girly moan escape my lips before taking him back into a french kiss as he continued pushing in and out of my ass getting faster with each stroke. He started pushing harder. He picked up the speed until I felt like he was actually fucking my brains outs. I was in heaven. In, and out. Faster and harder. In. Out. In. Out. In. He then stopped and rolled over, cock still inside me. I broke the kiss and sat up, pulling myself off of his cock. He grabbed my hips and slammed be back down into his groin. I knew what he was doing and I was so excited. I was about to go for the best ride of my life. He began bouncing me up and down, on his cock. I bounced on his cock in rhythm for what must've been 20-30 mins before he said he was about to cum. I stopped bouncing.

"Don't cum for me yet. There's one more first I haven't had yet." He looked at me questioningly as I stood myself up off of his lap. "Sit on the side of the bed." I took charge as I stumbled around it front of him and dropped to my knees. I took the condom off of his cock and licked my lips readily. I kissed the head of his cock and looked up into his eyes as he smiled. I began giving my first blowjob by bobbing my head up and down, slowly taking more and more of his cock into my mouth. I tried my best to control my gag reflex as I felt his member slide further, going back into my throat. I put one hand around the base of his cock and fondled his balls with the other, until he grabbed my head and pushed his cock all the way into my throat. I held on as I felt it spasm and tried to swallow as I felt all of the warm, sticky jets shoot out his cock and into my throat. As I was swallowing Phil's cum, I felt my own cock twitch and spasm as my own cum shot into the floor in front of me. I swallowed all I could of his seed, but some still leaked out and dribbled down my chin. He pulled his softening cock from my mouth as I used my fingers to clean up wipe the cum from my chin. I looked up at him and smiled before licking it off of fingers and swallowing it with the rest. He laughed and then moaned as I leaned forward and licked his cock clean.

"That was the best sex I think I've ever had. Damn, Tiff." He fell backwards onto my bed, legs still hanging off the side. I climbed up onto the bed and crawled on all fours over to him, laying my head on his still exposed chest.

"I had planned on just spending the weekend alone with my battery operated friend over there, but I'm glad you came over."

"Oh, that's right. I almost forgot you were alone this weekend. I forgot in all the excitement! So, what do you say? Want me to stay?"

"Oh yes. Definitely." I giggled. "I'm so hungry. Is it always like this after sex?"

"Good sex. Haha. Why don't we get cleaned up, get dressed, and go out to eat? The night's still young, maybe we can even hit the movie theater!"

"Philip, are you asking me out on a date?"

"I guess I am."

"I have nothing to wear... Hold on. I guess I'll go raid Tam's room for stuff." I walked clumsily to the door, much to Phil's amusement, since he knew it was because he had fucked me silly that I could barely walk. I stumbled in to Tamara's room and started going through her closet. I spied a knee-length black and grey sleeveless dress with a black belt around it hanging in the back and grabbed it. I went to my room and grabbed a new bra and panty set, red this time. As I went to change, I decided to call Tam. I had to tell her what happened. She knew my secret, and I tried to stay in contact after she eloped. Using her room to hide my stuff was her idea.

"Hello?"

"Hey, Tam. It's Tiffany. No, not Timmy. Tiffany! I have to tell you what just happened!" I recounted everything and even told her I was borrowing one of her dresses for our date. She told me she always knew i had it in me (literally). She said she was proud of her new little sister and couldn't wait to meet her soon. I got dressed and went back to my room to see Philip redressed.

"I'm ready when you are, love." He said.

"I just need shoes and we're good to go!" Crap. Tam's shoes won't fit. They're just a size too small. Wait. Mom's! Mom's would work. I'd just put them back when I was done, hoping she wouldn't notice. I grabbed a pair of plain back flats and headed to the door with Philip. I took one last look around the house and checked myself in the mirror before stepping out on my first date as a woman.