On A Mission

This is another story from my other account.

Ok, I've only done this once, I think, but this story is written from the other side. I've always been the submissive, but this story has been in my head a while. All characters are over 18. Comments, good or bad, are welcomed.

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I sat, in my favorite seat, in my favorite diner, watching her across the road. Sign out, panhandling for enough money for a meal, and, if he's really lucky, maybe some extra, probably for a bus ticket. Definitely looked lost. And desperate. And just what I'm looking for.

I was patient. It's a gift, and essential for my plan. I waited another 45 minutes, nursing my coffee. When it looked as if all hope had left him, I stepped out the door, gave a loud whistle. She looked up, and over, not sure of the signal. I waved her over, and she meekly walked over.

"Yes, Sir?"

"Come in, hon, I'll buy you a meal, and you can warm up." He looked puzzled that I said, "hon," but shyly nodded and stepped in, following me to my booth. "Order anything you'd like. I have a proposition for you." He looked unsure, but his hunger got the best of him, and he ordered. He ate hurriedly, at first, then slowed down, maybe trying to put off whatever I was going to say. I waited until the waitress filled our coffee cups again, and continued. "I'm Wilson", extending my hand, "You are?"

"I'm... Andrew, but usually called Andy. That you for the meal. That is the first thing I've had today. When it's cold out, people don't seem as friendly. Why did YOU buy me this?" (Ah, good, he's curious, getting right to it.)

"Well, Andy, I've been sitting here, watching you, for a while now. Honestly, I'm surprised no one else offered to help you. You are way too pretty to stand out there, begging." His mouth dropped open, and he blushed. He started to interrupt, likely to deny it, but I held my hand up, and kept talking. " No point in denying it, I'm confident you've had people tell you that you look like a girl. That's NOT a bad thing. In fact, it CAN be a VERY good thing. Tell me, honestly, are you HAPPY with your life right now? (Not waiting for an answer) Of course you are aren't. You are broke, obviously without any family support, or you wouldn't be out on the road."I can change that for you, if you are willing. You can be desired, treasured, even. You Do understand what I'm saying, right?"

He slowly nodded, and answered, "I... think so, but... I'm not... gay. I like girls, really."

I smiled, and continued. "Of course you do, but girls aren't paying any attention to you, are they? Girls don't go out with poor boys, even the pretty ones" He winced again. "AND, being with a man isn't gay... IF YOU are the girl, is it?"

"W-why do you think I could be a girl? Or, that I would want to be?"

"I'll tell you what. (pulling out my wallet) Here is a hundred dollar bill. You come with me, just for tonight, and let me prove it to you. If I'm wrong, the hundred is yours, and I'll give you a ride to the bus station. Sound fair? In fact, if at anytime tonight, you decide you don't like what I'm proposing, I'll STILL honor my word. Can't do better than that, can I?"

He sat thinking for a couple of minutes. I knew he was weighing the limited options he had. I stood up, ans said, "I'm going home Andi. If you'd like to come with me, get up. If not, it was nice chatting with you." I paid the tab, and tip, and stepped out. I was opening my car door, when he raced out, and sheepishly stood by the passenger door. "Good girl", I grinned, and patted his leg as I fired the engine up. He sat biting his lip as we rode. "Don't worry, Andi. So far, I've never been wrong about anyone, yet. You'll see, this is the start of your new life. Have you ever seen a real cock? Not that little thing between your legs, but a REAL one?"

He stammered, "In gym class, when we have to shower, there were guys... b-bigger than me." His face was so red now. I pulled his hand over to my crotch. He tried to pull back, but I held it on my bulge. Every time he'd try to pull it off, I'd push it back down, until he finally let it rest there, and oh so slowly, wrapped his fingers on it. I could see his chest heaving as his breathing quickened.

"Oh, Sugar, yes. Feel that, that's a real cock. Feel how it responds to your touch? Go ahead, unzip me and pull it free. I KNOW you are curious to see it." he turned his head to his window, and I put his hand on my zipper. He was shaking, but eased it down, and very awkwardly fished his hand in my jeans. I was still not fully hard, but when his fingers gripped bare skin, it swelled to life. "Oh, baby, yes. THIS is what a cock feels like. Come on, take a good look."

The road was dark, and I guess it may have made him feel a little safer, knowing no one could see him, and he turned back to me. His fingers went from light, cautious touches, to wrapping fully around me. "See? Not so bad, is it? It's exciting, isn't it? Taboo, but sexy, touching someone else." I reached over, unbuckled his seat belt. "Will you kiss it for me? It's just you and me here, no one has to know. If you don't like it, you don't have to keep doing it, ok?"

His eyes kept going from my cock, to my face. I wasn't about to force him, the choice had to be his. I almost started doubting myself, when he leaned down, an inch above my cock head, took a breath, and pressed his lips on the head. I think we both gasped. After a few seconds, he followed up with light kisses all around my smooth red, swollen head. "Oh, God, Baby, yes, that is sooo nice!" He kissed up and down the shaft, and I let my fingers softly comb through his hair. Not pushing, just letting him know I liked it. It took some time, but he finally opened his lips, and slid them over the head, taking me in his mouth. I wanted to cum right then. I LOVE when a sweet thing surrenders. My cock was pulsing, and I had to pinch the fuck out of my leg to keep from cumming. I wanted to make sure he was comfortable accepting my cock, before I filled him with cum, though.

After a couple of minutes of exploring, he looked up at me, with a blushing grin. I guess, letting me know that I was right, so far. "You are making me feel so damn good, Baby. I'm going to cum, if you keep that up." His eyes widened for a second, then he closed them and began going faster. THIS is going to be a great night!

I pulled the car over, because I wasn't going to last, and I wanted to concentrate on my young

friend's efforts. When I told him I was going to cum soon, he kicked it up a notch. I had lit the

flame of his curiosity, and once he accepted my challenge/offer, we both knew he was giving

in. My hips lifted as I shot the first blast into his mouth. He stiffened, probably surprised at the

amount of cum filling his mouth. And cum oozed out of his lips, as he swallowed. I shot a few

more blasts, each one a little less than the one before. His nostrils flared from breathing so

hard, and he softly moaned as he swirled the last of my cum on his tongue, before

swallowing it, too. The look on his face told me that he was living scenes that must have

entered his thoughts, at least once.

"D-did... I do ok?" I laughed, because he knew he had. NO one cums that hard from a bad blow job. Even though, as I mentioned before, I DO love taking a sweet thing's innocence. He grinned, licked his lips. It... wasn't what I expected, but, um, it was... ok... I think.

"Good! I'm glad you enjoyed it too." (Nothing like reinforcing that) It feels good to make someone else feel good... doesn't it? So, ready to go to my house, and we can continue making you into a new you?" He sat back up, nodded, then looked like he was deep in thought. Probably trying to decide what would happen next. We rode the next few miles in silence, but he would glance over, from time to time. He did tense up a bit, when I turned into my drive. A long, secluded lane, with a lot of tree cover.

"THIS is where you live?" I nodded, and he sat up straighter, when the lights drew in his attention. It is an old 2 story brick, but fairly well maintained. I hit the remote for the garage door, and we were immersed in light as I pulled in, then closed the door behind us.

"There's nothing to be afraid of, Andi, I'm not going to harm you. I'm going to help you, I promise." I opened the garage door that entered the house, and waited for him to climb out of the car. When he stepped in, I pointed down the hallway. "The living room is on the right. Sit down, relax, and I'll get us something to drink. Would you like a beer, or... something softer?"

He shot a smile. "Beer? Sure!" Good, I thought, maybe a buzz to take the edge off his nerves. While I was getting the beers, I shouted out that he could find something on the TV, if he wanted. As I sat with the beers, he was rifling through the channels. I handed him his, and took a long draw off of mine. He stopped at a football game, but only looked mildly interested. I wasn't fond of either team, so I wasn't that into it either, but was letting him relax at his own pace. After his second beer was empty, he sat the bottle down and took a deep breath. A lump catching in his throat as he squeaked out, " what do you want to do next? With... me, I mean?"

"Well, the next part is easy, for you, and, hopefully fun. Come on upstairs, I'll show you to your room, and we'll go through some clothing. Ready?" I pulled out my phone, called my next door neighbor. "Bernice, this is Wilson. I have a young lady that needs your assistance. Do you have time? She's here now. Oh, perfect! The front door is unlocked, let yourself in and come to the guest suite."

"Andi, Bernice is a dear friend, and is a beautician. She will turn you from the cute girl you are, to a knockout, trust me. Just do what she says, and pay attention to what she shows you." He looked nervous, probably worried that another person would be aware of his situation. "Don't be concerned, Hon, Bernice is discreet and knows her stuff. You will love yourself, when she's done!"

We heard the front door close, and moments later, Bernice appeared in the doorway. "Well, Wilson, you've outdone yourself! She is so pretty, already, without my help. I'm excited to get to take her to the next level. What's your name, Cutie?"

Andi stammered out her name, and Bernice hugged her. "Ok, then, Andi, let's get you out of these clothes and into the shower. We've got work ahead of us. You're going to love... most of it."She smiled a huge toothy smile. "Wilson, you just go back downstairs and do whatever it is you do, while Andi and I make her irresistible." So, I went down, made myself a drink and surfed the internet. I knew Bernice was thorough, and they would be a while. I was fairly confident that Andi would embrace the steps that Bernice would go though. After over an hour, I lay back on the couch and dozed off.

Bernice went through her regimen, using a dilatory on Andi's legs, having her shave all the tender places, teaching her to douche, showering, blow drying her hair, a crash course on makeup. (Not that she needed much, but attention to eyes and lips, and getting her dressed, painting her finger and toenails, AND, the bonus points; one, teaching her to walk in heels, and how to move, and sit like a female. Bernice shook me awake, to show off her work. "Wilson, open your eyes, and feast them on this girl!"

Andi stood a few feet from me, already blushing, hands behind her back, one leg slightly crossing the other, in a white lace blouse, black satin skirt, thigh high nude stockings, and 3 inch, ankle strapped heels. She blushed, yes, but from her smile, she KNEW, inside, that she was hot. She was watching my eyes, and her smile grew bigger when she saw my response. "Amazing, ladies! She's even sexier than I imagined." With that, Andi gave a little curtsy. (Obviously another one of Bernice's little touches. She was always coming up with something new) Bernice gave Andi a big hug, and said she needed to go get her beauty sleep. She knew that I would settle up with her later. I sat up, patted the couch next to me. "Will you join me, Andi? How do you feel, with your new look?"

She stepped over, concentrating on walking, AND sitting, as ladylike as possible (and she nailed it)

Clearing her throat, she answered, (in a more feminine voice, another of Bernice's tips), "I... like it... I can't believe it's me, but... it's e-exciting. Thank you... for... doing this for me." She turned to look at me, and I wrapped an arm around her. She had a "hopeful" look, as if her world had changed, and, of course, it had, and would. I leaned into her, eyes locked on hers, and pressed my lips to hers. She gasped, but closed her eyes and kissed back. YES, she's resigned herself to being Andi!

I pressed my tongue against her lips, and she opened them, gasping softly. Her left hand was on my chest, and I slowly eased it down to my crotch. Her eyes opened, but she kept kissing, as her fingers wrapped around my still confined cock. She instantly felt how hard she'd made me. Eventually, she started unbuckling my pants, and unzipping them, and pulling my seriously hard cock free. Her fingers felt magic, caressing, stroking, squeezing me. She pulled back, gave me a knowing smile, and dropped her lips to my engorged cock. No hesitation this time, she knew what I wanted, AND what she wanted. She licked, kissed and finally opened those red lips on my cock. I loved that she was moaning louder than I was. Three times, she brought he to the edge of cumming, and each time, I pulled her away. The last time, her pout got to me and I asked if she was ready to take me to bed. She knew what was coming, and may have been a little scared, but I could tell she was ready to be made a woman. I picked her up, cradling her, and walked her up the stairs, her arms around my neck, lips kissing my neck.

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{{This is the finale of this story. As I mentioned before, I'm not use to taking the male role, so it was an adventure, and I had to pull from my memories, things that were said to me, slathered with a bit of imagination. I hope this chapter is as well received as the other two. Thank you all for the kind words. <3 }}

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I was going to have to give Bernice a bonus. Not only did Andi look and feel sexy, she smelled divine. Andi was my third "turning", and Bernice, after struggling a little with my first girl, caught on quickly, and improved so much on my second find. But, Andi, fuck me, I would have to try hard NOT to fall in love with. Just like flipping a light switch, Andi so quickly realized who she was, and to this point, was embracing her new feminism. I figured I would have to coax her into setting the mindset of being a sexy, vibrant, woman, but, as soon as she saw herself, all dressed, AND saw my reaction to her, immersed herself in her new persona seamlessly.

I eased her to the floor, in front of my bed, and she did look a little nervous. Perfectly normal. It was a confident nervous, though. I was about to do something that I'm betting she never before truly thought would ever happen. I was going to take something from her that she wasn't even aware of, before today. After all, how many guys, who believe themselves to be "straight", EVER think a man is going to fuck all the maleness out of them, while coming to realize that they may WANT it to happen? There was a nervousness in her eyes, sure, but the was anticipation, too. I'd bet money that, somewhere in her thoughts, she wondered if she would please me enough. I knew, with absolute certainty, that before we fell asleep tonight, she WILL ask if she was good.

She reached her arms up, and around my neck, and very slowly ground herself against my bulge. That's right, little girl, make me want it, NEED it. Bernice did NOT teach her that, it came from her own mind. She may be inexperienced, but her desire, to BE desired, was so hot! She bit her lip, took a breath and asked, "Do you want to take my virginity?"

I cupped her ass cheeks, and asked, Do you want me to breed you?" That one caught her off guard, but she slowly nodded. I unbuttoned her blouse, exposing a thin lace bra, that was covering what appeared to be B cup silicone breast forms. They were perfect for her petite size. I unbuttoned her skirt, unzipped it, and pushed it down her hips. She stepped out of it when it hit her ankles. The bikini cut panties matched the bra perfectly. There was little, if any bulge in the panties, so I guessed that Bernice showed her how to tuck and tape. Standing in her undies, stockings and heels, she unbuttoned my shirt, then my pants, pulling them down to my ankles. She then knelt, lifted one foot after the other, taking my shoes and socks off. I let my shirt fall to the fall, as she pulled my boxers down to join the rest of my clothes.

She stood, grabbed my cock, and stepped backwards toward the bed. When she felt the bed against her calves, she released me, and fell backward on the bed, and inched herself up on the bed, and struck a "Hollywood" pose. Her eyes widened, when she must have remembered something Bernice told her.

"Oh, Daddy! Your... Cock... it's so big! Did I cause that?" Then she gave me a coy grin. Fuck me, she's a natural! She teased me further, saying, "Please, Daddy, don't hurt me with that big thing." Dammit, it's going to be hard NOT to fall for this one. I've awakened a sleeping beauty! My cock was so hard, it hurt. I leaned into her, kissing her as I eased my body on hers.

This wasn't going to be a fucking. Taking a virgin's cherry is special. Something she will always remember, either wonderfully, or badly. Andi is much too much a natural NOT to take the extra time and effort, and make her the desirable woman she is. Her lips, and body, immediately responded. Her mouth opened and her tongue danced with mine. Her arms went around my neck, then slowly wandered on my back and sides, while our hips moved side to side. My cock pressed against her stomach. I felt her small bulge against me as we swayed, just further reinforcing the desire I knew was building in her. I pulled away from her face, her eyes searching mine.

She probably wondered if she'd done something wrong, until I started with little kisses on her neck, shoulders, chest, and nipples She cooed as I drew them in my teeth, sucking them as deep in my mouth as they would go. Little gasps of "oh, my God!," as I went from one to the other. They were deep red, and swelling from the attention. She couldn't help herself, her nails were in my back, and her hips arching up into me. When she could take it no more, she begged, "Please, Daddy, I need you... "

Well, who am I to deny a woman in need? I kissed on down her belly, to her inner thigh, pushing those frilly panties to the side as I lifted her hips higher, and invaded her little pink star with my tongue. Her body bucked and she groaned. I tasted a bit of cherry flavored lube, (thank you, Bernice) but I kept swirling my tongue around, driving her desire. I figured she thought it would be just "Wham, Bam, thank you, Maam", that I'd just fill her, and cum. That's no way to make her want more. One of my hands reached up to her nipple, pulling gently, while the other hand cupped her clit through her panty. I felt her precum through soaked lace. She twisted and moaned.

"Pleeeezzzeee, Daddy! " I want you, now!! I need to feel it IN me!" I lifted her legs up around her head, and pushed my cock head to to her quivering ass, and pushed slowly. Her eyes got wide when my head popped in. She tensed up. Yes, she wanted it, but wasn't quite prepared for that initial shock. Her hand gripped my thighs tightly as tears ran down her cheeks into her ears. She bit her lip.

"It's ok, Baby. Relax, you will stretch. It won't hurt long." I reached over, grabbed the lube, pulled my cock back out, and coated it good. When I pushed the second time, she released a deep breath. "That's my girl. Take that cock, Baby." She opened her eyes and gave a shaky smile, and nodded. I was in about three inches. I backed out, then back in with four. Each time, she'd let out a grasp. When I had six inches in, I started swirling it around, and she started moving her hips in response.

"God, what are you doing? Th-that's SO good. More, please. I feel so full, but soooo good. F-f-fuck me like a girl! You were SO right about me!" with that she started bucking under me, and took all of me in her. Her chest was heaving, her face beet red and she sucked in air, and moaned. Her panties were soaked between us, having cum for the first time as a girl. I wrapped my hands under her, and flipped us over, so she was riding me. She looked stunned, but only took a few seconds to start rocking back and forth on me. She kept looking from my face, to my cock as it slipped in and out of her. "Ohhh, God! Yesss!!!" She smiled even bigger when she felt my cum shoot up in her, and she came again. She bucked on me until I was semi-hard, then fell on my chest, kissing me and crying. "I love you, Daddy!"