Aunt Maggie

In this part, Aunt Maggie and Christy role-play, based on scenarios determined by Maggie.

I won't tell you in advance what this story is about, but I can envision Maggie playing a madam for Christy's hooker. I can also see the game being played with Christy as a wife, and a secretary. Maybe even a blushing bride on her honeymoon.

Please let me know if you see other potential roles for her: lovepinkpumps@excite.com

Also, I never, ever refer to my star characters as "tgirls", "trannies", "shemales", etc. To me, they're simply "special girls". I think that makes them more feminine. And isn't that the point?

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Aunt Maggie Part 2 By Pink Pumps

Chapter 1

Two years later ...

My life with Aunt Maggie couldn't be more wonderful.

"Horney" just doesn't describe her since she turned me into Christy and I moved in with her. Whatever switches she has, I'm flipping them. I'm only 21 and can keep up, but her sexual stamina is pleasantly challenging, even though she's twice my age.

As you remember, I've only been fucked once, and it was great. But as completely as Maggie satisfies me, if I never got fucked again I wouldn't care. She does bring up the subject of me getting fucked again from time to time, but I always tell her she's more than enough for me.

But one night ...

"What if I asked to you to fuck a man?" she asked. "Would you? For me? And then tell me afterward about EVERYTHING that happened?"

"Maggie, I don't ..." was all I could get out.

"But what if I WANT you to, darling?" she asked again. "You told me you'd trust me and do everything I asked. Have I ever asked you to do anything you didn't enjoy? Did I ever make a promise I didn't keep?"

"No," I admitted without hesitation.

"So if I set it up, you'll let a man fuck you?"

I whispered, "If that's what you want."

"I DO, Christy! I want you to get fucked again. Darling, I want you to experience everything I did as a young girl. I want you to feel those things as Christy, and Christy has missed too much. You deserve it."

"But who?" I asked. "That sort of scares me. I mean, outside of the people at the office, no one knows I'm ... well, special."

"Do you believe everyone sees you as my beautiful teen niece?"

"Yes," I answered. "You made sure of that, Maggie."

"Do you believe I can safely set it up with someone you'd enjoy being with?"

"Yes. I promised I'd trust you, and I'll never stop."

"So it's settled then," she said. "Tomorrow night my wonderful Christy goes on a date and gets fucked again. I already know who it'll be, but you won't until he picks you up."

Maggie explained that her fantasy was for me to dress in a certain way, befitting the occasion she creates.

Wow!

Chapter 2

After we got home from work the next day, Maggie drew hot bubble bath for me, then washed and conditioned my hair.

By the way, thanks to our very talented hairdressers, I'm a ginger now, and we love it. Even my little landing strip is red.

I stood and she shaved my legs and trimmed my pubic patch. She patted me dry and applied baby powder.

Like she did when I was fucked in Part 1, she gave me a series of enemas and a scented douche. I didn't know why then, but I sure as hell did now. My pootie was going to be filled by only my second cock.

She dried and rolled my hair, then brushed it out and put it up in swirls. I've always worn my shoulder-length hair down, and it being up was an exciting new experience.

I would wear sterling-silver barrettes, sterling shoulder-brushing earrings, a sterling necklace with a diamond drop, and her silver Rolex. I have a Rolex that Maggie give me on our first anniversary, but it's gold and wouldn't have gone very well with what I was about to wear.

Maggie laid out a silver ankle-length evening gown with a slit over one leg that would rise to well above mid-thigh. The top was a lacy strapless bodice; the bottom was satiny smooth. The top would cradle and squeeze my 34Bs, displaying some cleavage, but just a hint. Keep `em guessing, right?

She helped me into a white-lace garterbelt and nude stockings that were so sheer they were almost invisible, but made my legs look incredible!

I wouldn't wear panties. Not even a thong.

As she zipped up the gown for me, I realized how very tight it was and what the slit was for. With no slit, I wouldn't have been able to walk. And each and every time I took a step, a whole helluva' lot of stocking-clad leg would show.

The hormones I've been on for two years have given my hips a nice flare. My ass was plump before I started them, but even more so now. The tightness of the dress left almost nothing to the imagination back there.

Next I slipped on a pair of glittering sliver, strappy, five-inch stiletto sandals. I've heard the term "barely there" used to describe heels like these, and that definitely applied. There was 1/2-inch strap across them, starting just above my toes. A much narrower strap crisscrossed my ankles and buckled. But I found them surprisingly easy to walk in. Maybe after two years of being Christy, walking in heels was becoming second nature.

Normally my makeup is very light – just some blush, a little pink eye shadow, black eyeliner, and pink lip gloss. Christy is a teen, after all, and I've been dressing the part. But tonight it was much darker. "Bedroom" makeup!

Maggie handed me a pair of white gloves that extended above my elbows. I pulled them on and looked at myself in the mirror. I swear a 16-year-old girl was looking back! Maggie is a magician, and nobody outside our office world has ever known me as anything but her teenage niece.

Just as I was spritzing on my perfume and applying the final touches to my makeup, the doorbell rang.

"Wait `til I call you," she said and headed down the stairs.

I could hear voices, so I knew my date had arrived. I'll admit that I was nervous.

Then I heard Maggie say, "Christy, come down!"

Well, it was time to meet him. Whoever he was.

I was still at the top of the stairs when I saw him for the first time. He was no older than 17! (Legal age, by the way.) And a very handsome, too. Damn, this was going to be HOT. Is Maggie great, or what?

When he saw me, his eyes widened. I suppose he liked what he saw! Right?

"Christy, honey, this is David," Maggie said.

He thrust out his hand, and I thought it was to shake mine. But then I noticed – holy shit – he had a white orchid corsage for me!

I blushed! A 17-year-old boy made me blush! Maggie helped me pin it on, then I kissed his cheek.

"Thank you," I said. "It's beautiful."

He still hadn't said ONE WORD and Maggie hadn't told me what she had planned for us.

Maggie led us to the door, kissed us both, then whispered in my ear, "Senior prom."

So that's how our game would go. I wouldn't know what I was dressed for until I got to the door. This was going to be FUN!

(Just so you'll know, David is the son of one of Maggie's well-vetted friends; he'd seen pictures of me and had the hots.)

I took David's arm and he led me to – holy shit, yet again – his sparkling, black four-wheel-drive pickup truck! He opened the door for me and helped me in. And I needed it! The tires on the thing were huge, and even with the slit in my dress, it was an adventure.

My dress parted at the slit enough so that he got an eyeful of a stocking welt and a garterbelt strap. He stared. And that was just fine with me! I was beginning to get the idea that he was really excited to be with me. But he still hadn't spoken.

The truck seat was a bench, so I scooted over against him, wrapped my arms around his neck and said, "David, please. You're going to have to relax. I'm really happy to be with you. Are we really going to your senior prom?"

"Yes," was the first word I'd heard him say.

I kissed his cheek and said, "I'm very flattered! I really am! And, sweetie, you're going to have to loosen up."

Then I noticed the bulge in his tux pants.

"Did I do that?" I asked.

He nodded.

"David!" I laughed. "If I'm going to be your prom date tonight and dance with you, you have to talk to me!"

"Okay," he said. "You're beautiful."

Well, that was a good start, right?

I placed my hand on his bulge and squeezed. "You flatter me again, David. Am I your first?"

"Yes," he replied. "You're beautiful."

"Thank you, but you already told me that," I giggled. "And I think you're a hunk, honey."

He said, "Maggie told us this was the first date you've ever had."

And technically it WAS my first date as Christy. I mean, Christoper had had a few dates, but not Christy. And the first time I'd been fucked was when Maggie took me to a hotel and was in the room as a faceless, nameless, rent-a-dick took my virginity. Don't get me wrong, I loved EVERY SECOND of it, but I guess that really didn't count as an official date, huh?

"This is my first date, but I've ... well, you know ... done it once before. But it's been two years. I feel like I'm a virgin again out with a handsome boy!"

So then I asked, "So am I YOUR first?"

"Yes, you are," he replied, and gulped.

I squeezed his hard cock again, then said, "Find someplace private, and I'll take care of that. We can't have you going to the prom with a raging hard-on, can we?"

He pulled in behind a strip mall and turned off the motor. I unzipped him and helped him pull down his tux pants and tighty-whites. A very respectable six-inch dick popped out. Circumcised. Pink blub. Lighter pink shaft.

I removed one of my gloves and began to stroke.

"Has anyone ever done this for you?" I asked.

"A couple of times," he replied. "But no one as beautiful as you."

"Okay, sweetie!" I giggled again. "For every time you say I'm beautiful, I'm going to say you're handsome. And I promise you this, HANDSOME! When this night is over, you won't be a virgin."

After about 20 strokes, he started to breath hard and I could feel his cock starting to spasm. I wiggled down far enough to get my head between his cock and the steering wheel, then said, "We can't have cum getting on your tux pants, baby."

I managed to get my mouth on his cock just as he came, and I continued to suck until he went soft. I swallowed it all, helped him zip up, and patted his crotch.

"Feel better?" I asked.

"Christy, thank you," he said.

"Oh, babydoll," I whispered in his ear, "you're going to pay me back with interest before the night is over."

I swear he got hard again. Ah, youth!

Chapter 3

As David led me into the hotel ballroom packed with high-school revelers, a couple of thoughts hit me: I was such a nerd before becoming Christy, I'd never been to a prom. Not a single one. And I certainly had never danced in five-inch heels!

I guess I did a good enough job dancing that I didn't embarrass myself. Or David. But people still stared at us. Handsome David had a date with a princess. And I most DEFINITELY looked like a teen princess. (Thank you, Maggie!)

Looking back, I still have no idea how Maggie knew plain, drab Christoper could become beautiful Christy. I know the ugly duckling turning into a beautiful swan is a fairytale, and my life felt like a fairytale. But thanks to Maggie, this fairytale was reality. I owe every ounce of happiness I have to her.

As David and I slow danced, I wrapped my arms around his neck and he placed his hands on my waist above my hips.

"It's so crowded no one can see your hands," I said. "Don't be shy."

He got the message and cupped my asscheeks.

"How do you do it?" he asked.

"And what would that be, baby?"

"You know ..." he whispered. "I've never seen a girl as beautiful and feminine as you. How do you ..."

I had to giggle at that. "Because I know what you want. You see biological girls every day in torn-up jeans, t-shirts and black Chuck Taylor's.

"I on the other hand," I said, actually laughing, "know how to dress like a lady for a real man like you."

"Yeah, I get it," he replied. "You're beautiful."

"David," I said, "don't stopping saying that to me. I know I told you to stop with the beautiful stuff, but I can't lie – I love hearing it."

I initiated the kiss that followed, but he took the initiative on the tongue thing.

I could feel us both erecting, so I had to ask, "You're okay with me being ..."

I guess he knew what was coming and stopped me, saying, "Christy, look around and see if you can find someone as beautiful and feminine as you."

(That's my boy!)

"Let's go outside," I said, grabbing my purse off our table nearby.

We found a dark spot, I hiked up my dress, and gently dropped to my knees, making sure I didn't destroy my sexy stockings. I unzipped him again for a proper suck. I started at his peehole and cupped his balls. I licked up and down his shaft before taking it all. It wasn't long before he squirted in my mouth again. I sucked him dry, then cleaned the remaining cum off my lips with some tissue I had in my purse.

He helped me to my feet and said, "The prom is almost over and I know a perfect place to go. Uh ... I mean ... if you want to go."

"Honey," I said, "I'd be disappointed if you didn't take me to your perfect place."

We headed for his truck. My heels clicked on the pavement and my garterbelt straps tugged at my stockings. I will NEVER get tired of that sound and that feeling.

Chapter 4

I guess we drove for about 30 minutes, then David turned onto a gravel road. If he parked and fucked me on his truck seat, I'd be perfectly okay. But he kept driving. Then the road turned to dirt ... then to mud ...

David engaged the four-wheel drive and we moved easily through the ruts.

"Where ..." I said. Meaning to ask, "where are we going?", but he cut me off and smiled. That smile of his is dazzling! And it made me so fucking horney for him.

"Just hang on," he said. "Almost there."

As we rounded a curve, the truck's headlights illuminated and old cabin. I mean, it was 100% private, and all that, but ...

"Don't be fooled by the looks," said David.

He stopped the truck, we go out, and he led me up a cobblestone path. As uneven as it was, I had a hard time balancing in five-inch heels. But David grabbed me under my arms and supported me the rest of the way. My hero!

Once inside, I knew what he meant by not letting the looks fool me. It was immaculate and super impressive! It had a vaulted great room with a stone fireplace. Books, fishing tackle, hunting gear, high-def satellite television, sound system ... it really WAS perfect!

I sat on a couch and crossed my legs. The slit in my dress opened, and a LOT of my bare thigh showed above my stocking top. David went to a refrigerator and brought back two cold beers. I pulled my gloves off and accepted one.

"Having fun?" he asked.

"You have no idea," I answered.

"Uh, well ... could I ... uh, ask you something?" that sweet boy stuttered and stammered.

"Let me guess," I said. "You want to know about Christy."

He nodded, so I told him the whole story of how Aunt Maggie rescued nerdy Christoper and turned me into Christy. When I was done, he pulled me onto his lap and touched my stocking-clad thigh. As much as I wanted my first cock, I wanted his more.

"Take me to bed?" I almost pleaded.

"Can you spend the night?" he asked.

I pulled my cell out of my purse and called Maggie. I swear she screamed in delight when I told her I was staying all night with David.

"I'm all yours," I said.

We moved into the bedroom, and he and pulled a gift-wrapped box from beneath one of the two double beds.

"Wow!" I squealed. "Aren't you full of surprises?"

I opened the box, and inside was a pink and very sheer babydoll nighty; opaque white thigh-high stockings with pink bows at the top; and a pair of pink, satin, five-inch come-fuck-me pumps.

"Maggie told me you like pink heels and stockings."

"Ooooh, honey," I sighed. "Beautiful! Want me to put this on for you?"

"Would you wait a little?" he asked shyly. "I've never ... I mean ... I know you're wearing a garterbelt, and ... well, I've never seen a girl in a garterbelt, stockings and heels. I guess I have, but only in pictures on the internet."

"David!" I teased. "Checking out girls dressed only in garterbelts, stockings and heels! Naughty boy!"

I turned and asked him to unzip me. I let my dress fall the floor, and stepped out. I guess it was no longer a secret that I wasn't wearing panties.

I took the barrettes out of my hair, then shook my head slightly. My hair fell to my shoulders and I stroked my fingers through it. Even though tonight was the first time I'd worn my hair up, I'd seen Maggie do the same thing when she wore her hair like this. I thought it was incredibly sexy.

But then all of a sudden, I was really kinda' scared. What if I turned around and he was grossed out? What if he thought I was a freak? I hesitated.

Well, he took care of that, taking me by the shoulders and turning me to face him. He didn't glance below my boobies and their the rock-hard nipples.

"You're beautiful," he said. "I know I'd better stop saying that, but ..."

"You damn well better not!" I giggled. "I should never have told you to stop. What girl doesn't want to be beautiful?"

David just held me for awhile, and I laid my head on one of his shoulders. This was just as sweet as it was hot.

He broke the embrace and said, "I've never been with a girl as pretty as you."

"Only pretty?" I cooed.

"Okay. Beautiful."

"I'm glad you like me. You've seen all of me, now show me all of you. But I want to undress you."

That was soooo much fun! The first and only time I'd been fucked, as you remember, the man was naked when Maggie and I got to the hotel room.

So there we stood, staring into each others eyes. A virgin boy, and a girl who'd never been to a prom.

Chapter 5

We laid on the bed for awhile. Kissing. Me stroking his cock. Him groping my ass. Fondling my titties ... so hard it was actually hurting!

I gently pushed him away and said, "Sweetie, my boobies at sensitive. Especially my nipples."

Then it sort of dawned on me that he was as inexperienced with a girl as I was with a man.

Still, I had to wonder why David was a virgin. High-school girls should be throwing their panties at him as handsome as he was. Then I remembered how shy he is. Sweetly shy, for sure, but still shy.

"Look, baby," I said, "place your lips over a nipple and suck very lightly. Both nipples will erect, and when they do, use your teeth to nibble them.

"But DON'T BITE!" I giggled.

He took a nipple softly into his mouth and sucked. Soooo much better!

"Okay. Perfect," I said. "Now flick your tongue across my nipple."

He did, and I gasped in pleasure.

Then I felt his teeth. I squeaked and came!

"Oh, god," I hissed. "Now switch to my other boobie."

As he did, I almost frantically stroked his cock with one hand and fondled his balls with the other. I could feel him start to hump, and I knew he was getting close.

I took my hands off his package, placed both on his cheeks and said, "David, not yet. I want you to come inside me. I want to feel it."

He moved onto his knees, and I laid back, spreading and raising my legs. "Grab my heels and hold my legs back. I want to be completely open for you."

After the monster cock I took in the hotel room – even though that was two years ago – I felt like I could take all of him in one stroke. He aimed at my hole, then pushed all the way in. My pootie spasmed and I came again.

We fucked like that for awhile, then I asked him to let go off my heels so I could wrap my legs around him.

I moaned, "David, I'm so glad I'm your first. I hope I'll be your best. Best ever. Fuck me. But go slow. If you go too fast, you'll cum too fast. We both want this to last, don't we?"

I could see him nod, and I giggled once again, "Honey, talk to me!"

"Yes, I want this to be my best," he said. "I can't believe how good this feels. Does a pu ... "

I interrupted him, actually laughing a little: "You were going to ask `does a pussy feel this good'? Baby, pussy is great – I can't deny that and I hope you get plenty of it – but what I have his better. I'm tighter and I have more muscle control."

I clamped down on his shaft with my pooper muscles, then relaxed. "Feel it?"

"Ugh ah," he sighed.

I guess "ugh ah" meant "oh yeah", right? Whatever it meant, I knew he liked it.

We began to synchronize our movements, and it was so sweet and intimate. My first cock was very good, as I keep saying, but even though David's is smaller, I could feel more off it. He's still big enough to give me that wonderful, submissive, full feeling.

After 10 minutes, David started moving in and out faster. I thrust back, knowing we were both getting close.

We both moaned loudly and came at the very same time. That was the THIRD orgasm a 17-year-old boy had given me.

We slowly ground against each other as both of us caught our breath. He went soft and popped out, his cum dripping from my hole.

"Look down, baby," I said. "That's your love juice. You filled me up."

"So you thought I was good?" he asked.

"No," I replied.

"No?" he asked. He looked shocked – and maybe a little hurt – since I'd cum three times.

"No, honey. Not good. You were GREAT!"

We cooled our jets for awhile, then I got up and went into the bathroom, taking the gift box with me. I stripped out of my garterbelt, stockings and heels. Then I sat on the toilet and peed. I wiped, then while still sitting, I rolled the stockings up my legs.

Maggie has wonderful taste – the pink bows on the thigh-highs was just perfect!

I stepped into my pink pumps and joined David on the bed again.

After hugging and kissing until he was hard again (Didn't take long!), I rolled over onto my tummy, pulling a pillow under my mid-section. With my ass elevated, I spread my legs, then reached around and opened my bootie-cheeks. I don't know if David noticed my pink pucker the first time, but it was impossible to miss now.

David entered me again, and fucked me HARD. I came for the fourth time! I could get used to this young man.

Final Chapter

The next morning, I found myself alone in bed, but smelled coffee brewing and bacon frying.

As I got up to head to the bathroom, I noticed one of my overnight bags on the dresser. Obviously my sweet boy placed it there while I slept. I opened it and found a note. It read:

"My dear Christy,

"I don't have to ask if you enjoyed the prom. I know you did. I was hoping you would spend the night with David, so I packed a bag for you.

"I guess if you're reading this, it happened just like that.

"Love,

"Maggie"

Inside the bag was a makeup kit, toiletries, and clothes.

I took a shower, brushed my teeth, then applied very light makeup.

I was going to brush my hair, but I thought I'd leave it with that "just fucked" look. I had a feeling David would like to see "the fruits of his labor." Thinking of it like that made me giggle. He certainly had not disappointed.

Also in the overnight bag was a white butt-flosser thong, khaki miniskirt, baby-blue singlet, and pair of baby-blue Mary Jane's with four-inch stiletto heels. David seemed to like me in heels, and I damn sure wanted to dress to make him happy. I know Maggie hooked us up, but I still owed him.

I put everything on and headed into the great room. David was preoccupied preparing breakfast and didn't hear me. I walked up behind him, looped my arms around his waist, then kissed and nibbled ear.

"Thank you for everything," I whispered. "Thank for giving Christy something she's never had. Something she never DREAMED she'd have. It was perfect. I'm glad I had that experience with you."

After breakfast, he helped me into his truck, I moved over close to him, and we headed home.

After a few minutes, David said, "I hate for this to end."

He looked like a puppy! A sweet puppy!

"Why does it have to end?" I asked.

"Well, I know this is a game to you and Maggie."

"David, it STARTED as a game, but it ENDED being far more than that," I said. "Maggie wants me to experience everything she did when she was young, and I will. There will be other games. I love her for that.

"But that doesn't mean I won't have room for you in my life, and with Maggie's blessings," I continued. "Christy has a lot of catching up to do, and I want you to be part of it. I mean, if you want to be part of it. Do you?"

"Oh yeah!" he said.

"Don't you mean `ugh ah'?" I teased

"You made me do that!" he said and turned beet red.

I kissed hm on the cheek. "You made me do things, too, sweetie. Didn't you hear me? Those are just sounds two people make when they're happy."

"So we can do this again?"

"I don't see why not."

"Next weekend?"

Again I said, "I don't see why not."

"Well, there's ... well ... you see ..."

I interrupted, "David, you DO NOT have to be shy with me ever again! Didn't you gain some confidence last night? Don't you know you made girl you think is beautiful cum four times? A girl who looks forward to being with you again?

"So ask me," I said.

"Okay. There's this party at this lake. We'll drink beer, go swimming, maybe go boat riding, then build a bonfire that night. Do you have a bikini?"

I laughed. "Of course I have a bikini! I'm a girl! I have everything!

"How `bout this," I continued. "I'll wear my hair like it is now. That'll let all of your friends know we just did the nasty. We will before we get there, won't we?"

"Ugh ah," said David.

"Oh my goodness!" I laughed. "I guess I'm FINALLY getting you to relax. And think about this: None of your friends know me. We'll tell them I'm in college. How impressed will your friends be with that? David's fucking a college girl!"

That made him smile that sweet smile of his.

We'd made it to the gravel road, but not the highway.

I said, "Stop the truck."

"Why?" he asked. "Is something wrong?'

"Yeah, there's something wrong."

I took a dramatic enough pause, then said, "Neither of us has ever fucked in the back seat of a car. But in this case, it'll be in the cab of a pickup, and to me that's even hotter."

I slid over, laid back against the passenger door, lifted my singlet over my bare boobies, and pulled the hem of my skirt up. I placed one heels on the dashboard and the other on the top of the seat back. Then I pulled the thong's butt flosser to the side, giving him another good look at my tiny pooper hole.

"Come on in," I said. "The water's fine."

A note from Pink Pumps:

I mentioned at the top I want Maggie and Christy to continue role playing. If you have ideas, please don't hesitate to email me: lovepinkpumps@excite.com

I respond to all emails. If I haven't responded to any you sent after reading other stories, note that my email address has changed. Sorry about that.