Becoming Samantha! Pt. 02

A week later, we walked into Angelo's condo. Clare and Angelo clasped hands and kissed each other on both cheeks, European style. "Clare, my darling. It's been too long, you're as lovely as ever."

"And you're as big a flatterer as ever. Lo-Lo, this is my baby sister, Sammie."

Angelo put his hand over his heart. "My, you're even more beautiful than your big sister said. I know I'm going to enjoy this; I hope you will too. Off with you Clare. Come back in one half hour, we won't be long."

Clare smiled her reassurance at me and left.

"What the hell can he teach me in half an hour?" I thought to myself. Although I had to admit to myself, he was gorgeous. He was so good-looking; I wasn't sure that Sam wouldn't be attracted to him!

He walked around me once, then stopped in front of me. "Off with your clothes, darling." he said matter-of-factly.

"Well, that's not very romantic." I blurted out without thinking.

Angelo laughed. "I am not here to romance you, Samantha. I am here to teach you. Your sister told me you have never been with a man before. You are not ready for me to romance you. I want to see you naked so I can make some suggestions."

Blushing, I began to take off my clothes until I was standing in front of him in just my bra and panties. "Please take off everything. I will say I am happy to see that your lingerie matches. That is good. It shows that you care about all of your appearance. A man is a very visual animal. Purple panties and a green bra would be tacky and a turn-off."

I blushed even deeper if that was possible and took off my bra and panties. I was standing completely naked in front of this beautiful man whom I had just met. He walked around me, inspecting me like I was a piece of meat in a butcher shop. He knelt behind me, grabbed my cheeks and spread them. He put his nose right next to my bunghole and sniffed. "This is also good." he said. "You douched just before you came over. It would never, ever do for a man to be able to smell anything but freshness back there, especially given that is your only hole to please him with."

Angelo stood up. "You may put your clothes on. I will be right back." He walked out of the living room. I hurriedly got dressed. Even though he had seen me naked, I was still embarrassed and wanted to be dressed by the time he returned.

He came back with a dildo in each hand! One was about 8" long and fairly thick. The other was probably 6" long and a little thinner. "Here is part of your homework assignment. I want you to practice putting the smaller one in your ass until you can take it comfortably. Use the larger one in your mouth. You will need to practice breathing only through your nose the deeper you are able to put it in." He left and came back with a large tube of edible lubricant. "This will help you to minimize the pain in your backside as you get used to having something in it."

"Watch the movie 'Deep Throat' at least once a day. Pay close attention to the Linda Lovelace character; you can learn about technique from her. Buy a box of those, those, what do you call them??.... Gogurts! That's it. You know the yogurt in a flexible tube?"

I nodded.

"When you are ready to practice swallowing, cut them in half, and then squirt all of one of the halves into your mouth at once. When you can comfortably swallow all of it without gagging, you'll be ready. Also, when you masturbate, catch it in your hand and eat it. I want you to get used to the taste of cum in your mouth. You'll find that no man tastes exactly the same. A lot of the taste depends on his diet and health."

"Finally, I want you to douche daily. Douche after every time you go to the bathroom. Always, always keep yourself fresh back there. You always want to be ready."

"Do you have any questions?" I shook my head. "Good. Call me when you feel you are ready. Don't call me in the next two weeks. I want to make sure you are ready, and I am going to be out of town. Duty calls!"

Just then the doorbell rang. It was Clare picking me up. She and Angelo exchanged pleasantries again and we left.

"We need to stop at the grocery store. I have to pick up douche and Gogurt."

Clare looked at me wide-eyed. "My, that's an interesting shopping list."

I told her about my session with Angelo. She clapped her hands in delight. "I knew he would be able to help you."

I practiced daily over the next two weeks. I followed a strict regimen. The dildo in my ass was difficult at first. It was painful but I took my time. Once I got past the pain point, it was relatively easy and soon I was pleasuring myself with it. I remembered to catch my cum and eat it. It was creamy and salty but not unpleasant at all. I gagged on the Gogurt at first but by the end of the first week, I was able to swallow both halves of a tube with ease. When I could take the 6" dildo in my ass, I switched to the larger one. Soon, I was pounding my ass with that one. I also watched 'Deep Throat' and practiced on the dildos pretending I was Linda Lovelace.

And of course, my lessons with Clare continued. She made me start putting on my own makeup. I was dressed as Sammie every moment we were at home together. I was becoming more and more comfortable as Sammie. Sometimes it almost felt like Sam was disappearing.

By the end of the two weeks, I was easily able to take either dildo in my mouth or ass with no discomfort at all. I could swallow the half tube of Gogurt without gagging. I was enjoying the taste of my own cum and looking forward to tasting another man. I got a text from Angelo.

"How is your homework going?"

"I think I'm doing really well. No more pain, no more gagging, everything seems easy and natural."

"Can you come see me tomorrow?"

"Yes. There's nothing on my schedule."

"Please arrive promptly at 1:00 pm."

"Certainly, thank you Angelo."

"You can thank me tomorrow."

I rang the doorbell promptly at 1:00 pm. Angelo answered the door immediately, already naked. "You certainly don't waste any time." I said.

"I have a professional appointment at 4:30; I can't be late. That is what pays the bills. That is what allows me to live in this beautiful place and drive a Jaguar F-type coupe. Come in, come in, let's not waste any time. I want to see what you have learned."

I stepped into his condo. I was dressed in a smart business skirt suit. Not too much makeup, not too little. "I approve of your choice of clothing. When you are unsure of a situation, professional dress is always best. Now please go into the bathroom. I left some clothing there. I want you to put it on, nothing else."

I did as he asked. Inside I found a black satin waist cincher with eight garter straps, sheer black back-seamed stockings with reinforced heels and toes, 4" stiletto heel black satin mules with marabou feathers on the vamp, and 23" black satin opera gloves with open finger tips. There was also a rhinestone jewelry set consisting of a pendant necklace, dangle earrings, two choker bracelets, and four rings. I put the rings on the pinky and index fingers of my left hand and the ring and middle fingers of my right hand.

I turned to look in the full-length mirror on the door of the bathroom. I looked like a 1950's pin up girl or a high-priced call girl, depending on your point of view. I had to admit, I looked hot. Not just hot but steaming. Sex was exuding from every pore in my body. My look seemed to scream, "You want me. You know it and I know it."

I walked out of the bathroom and Angelo was sitting in his recliner. "Please come over here, kneel down, and show me what you have learned."

I waited, just posing for Angelo. His eyes drank in the sight of me, and I could see his cock start to twitch. Only then did I model-walk over to him and kneel down. "That is good, you understand how important it is to let your man get a good look, a really good look at you."

I reached out with both hands. I wrapped one hand around the base of his cock and with the other hand gently cupped his balls. I barely tickled his testicles with my fingertips, fully understanding how sensitive they were and not wanting to bruise him in any way. I pulled his now fully erect cock to my face and began to rub it against my cheeks and lips. Whenever it passed over my lips, I flicked my tongue at it as it went by.

Angleo cupped my face in his hands, so I had to look at him. "This is wonderful. You have already learned not to just jam the cock in your mouth. Even with a blow job there can be foreplay." He let go of me and leaned back in his chair. I continued to minister to him, even allowing the finger of the hand cupping his balls to gently trace his perineum from anus to the base of his scrotum.

I took just his prick into my mouth and slid my tongue under the rim of his mushroom. Angelo moaned appreciatively. I slowly allowed my lips to glide down the length of his shaft until my nose was buried in his pubic hairs. Then I just as slowly rose back up, licking and sucking every inch of the way. I looked into Angelo's eyes as I continued to bob up and down his shaft. I wanted him to know I wanted him. I wanted him to know that sucking his cock was the only thing I wanted to be doing.

Angelo smiled at me languidly, his fingers intertwined gently in my hair. He was caressing me, letting me know how much he enjoyed my oral ministrations. I continued to suck his cock, trying to remember every trick I'd seen Linda Lovelace use in the movie. Angelo's breathing started to become more shallow and rapid as his body tensed up and his hands pulled my face to his crotch with more urgency. He erupted without warning, bathing the back of my throat with sticky rope after sticky rope of his salty goodness.

Angelo tasted wonderful; clearly his diet and exercise regimen had him in tip-top shape physically which translated to tip-top taste! And the exercise he'd had me do with the Gogurt worked perfectly. I easily swallowed all of his cum and licked the slit in his prick to make sure I got every drop of his love juice.

Angelo collapsed into the chair. "Sammie, that was amazing. If that truly was your first blow job, you are an A+ student! Not only are you technically excellent, but your enthusiasm takes the experience to another level. Many women are technically proficient but not enthusiastic. Many women are enthusiastic but not technically proficient. You embody both of those characteristics; men will want to come back to you again and again!"

I smiled at him and crawled into his lap. His praise made me want to cuddle with him. I kissed him gently on his upper chest and neck, licking in between kisses. He lifted my chin and with his hand on the back of my neck, brought my face to his, kissing me urgently. His other hand was caressing my nylon-covered thigh, the feeling that brought was electric. I was shivering under his touch.

He gently stood up, steadying me as he did so. He took my hand and led me into his bedroom. He had me lay down on his satin sheets. "Now pose for me. If you are going to be a seductress, if you are going to be that woman every man wants in his bed, show me."

I thought of all the ways the women I had masturbated to online had posed. I started by lying on my hip and elbow, looking at Angelo with longing in my eyes. I was licking my lips while one hand traveled up and down the length of my stockings. While still looking at him, I rolled onto my back, my legs spread and knees up. I tweaked my nipples with one hand while the other hand played with my silicone vagina.

Angelo smiled. "This is good. You make me hard again, showing me how much you want me. You are so hot; you can't even wait for my hands to caress you in those places." He got onto his hands and knees on the bed and began to crawl towards me. His hands replaced mine as he began to play with my tits and finger my vagina. "There is a tube of edible lubricant on my nightstand. Take it and squirt some up your ass."

I did as he asked. It felt cool and slick inside me. Angelo placed the head of his erection against my rosebud. I'd fucked myself silly the last two weeks with the dildos he had given me in preparation for this moment. This was going to be different. I was going to lose my virginity to my sexual mentor and teacher.

He eased himself into me, slowly taking his time. I wanted him but my asshole had different ideas. "It's OK, Sammie. You're going to be nervous your first time." He continued to press against my rosebud and his prick began to slide inside me. I gasped as the sensation of his hard cock penetrated me. The warmth of his penis was incredible compared to the cool hardness of the dildos I had been practicing with.

"Mmmmmmm, yes, yes, Angelo. That feels so good. More, I want more of you, no, I want ALL of you inside me."

Angelo smiled as he continued to ease himself into me. I was moaning as he pinned my hands to the bed with his own. Finally, his balls were resting against my ass cheeks. I wrapped my legs around his waist, locking my ankles behind his back. I started rotating my hips around his shaft while I squeezed it with my ass muscles.

"Angelo, this is who I was meant to be. Fuck me, make me a complete woman. It feels so wonderful to have you inside me. Take me, take me now, oh fuck me, please fuck me!"

Angelo began to slowly slide back until just his prick was inside me. Then he would slide back in just as slowly until he was buried to the hilt. He gradually began to pick up the pace until he was pounding my ass furiously. I was starting to get tingly inside; I'd never felt like I was going to cum when I was using the dildos, but this felt like I was getting ready to orgasm.

Just then Angelo stopped. "No, please don't stop. Lo-Lo, I'm so close. Please!"

He reached behind us and uncrossed my ankles. "On your hands and knees, Sammie. We want you to experience as many positions as possible during this session."

I groaned in frustration but did as Angelo asked. He positioned himself behind me and placing his hands on my hips, thrust completely back inside of me in one motion. We got into a rhythm quickly; I would rock forward when he was pulling out and rock backward as he was thrusting in. All of a sudden, on one of his deeper thrusts, the tip of his cock brushed me somewhere inside and I lost all control. "Fuck me Lo-Lo, fuck me. Mmmmmm, so good, so good, so good. Nnnngggghhhhh, FUCK ME!"

"Aaaaaaaahhhhhh, I was wondering if I would find your P-spot. I want you to enjoy this my beautiful Sammie!" And with every thrust, his prick rubbed my P-spot over and over and over. I couldn't get hard inside my prosthetic, but I could still feel myself close to cumming.

I looked over my shoulder at him and licked my lips seductively. "Lo-Lo, you beautiful man. Fuck this pussy, take my cherry. Make me cum for you, mmmmmmmmmm, I have to cum for you."

He just smiled at me and continued to fuck me like a metronome, hitting my P-spot every time. "Angelo, shit, oh stop, please stop. Too good, feels too good. Stop, stop, stop. No, no, no. Don't stop, don't stop, don't stop. Fuck this pussy, fuck my pussy, FUCK MEEEEEEEEEE!!!!"

I collapsed forward onto my elbows, my ass still high in the air. Angelo began to slide his hands up and down my stocking-covered legs, from thighs to ankles and back again. That feeling sent me over the edge and I began to cum again and again and again. "Uh, uh, uh, shitfuck, shitfuck, shitfuck. Cu-cum-cummmiiinnngggggg! Oh, oh, ohhhhhhhhhhhhhhh! Mmmmmmmmmmmm, nnnnnnnngggggggggggggghhhhhhhhhhhh!!!!" I lost all rational thought; my brain was on fire with the sensation of cumming again and again and again.

When I was able to regain some semblance of rational thought, I realized we were laying on our sides. Angelo was behind me, spooning me, holding me, kissing the back of my neck, one leg draped over me. I could feel his sperm oozing out of me. I was no longer an inexperienced girl jerking a boy off in the back of a movie theater. I was a woman and the man I was with had cum twice because of me.

"Samantha, you are amazing. You are beautiful, desirable, and marvelous in bed. If I didn't have an appointment in a little while, I would want to spend the rest of the day making love to you. But I have somewhere to be. You need to get cleaned up and leave so that I have enough time to clean up before I meet him."

"Him? Your afternoon appointment is with another man?" I asked incredulously.

"Yes. Why so surprised? I know that Clare told you I am bi-sexual and that my clients include both men and women. He is one of the most powerful men in the city, no, the state. He is also very generous. He demands punctuality and so I must make sure I arrive on time. Please do as I ask. You may keep the clothes. Not only does it fit your body, but it fits your personality. You look like a goddess in that outfit. Now go."

I did as Angelo asked, quickly cleaning myself. I wanted to stay but I also wanted to get out of his way so he wouldn't have to rush to get ready for his appointment. I gave him a quick kiss and headed out the door.

My reminiscing over for the moment, I looked at Jake, Robbie, and Teddy. "All right, all right. I'll do it, I'll dress as Dorothy for the damn costume contest. But we better win if you guys are going to make me go through all this. And I hope Clare is a miracle worker so she can help me look something, anything like Dorothy at all!"

The three of them cheered simultaneously and we did our Fearsome Foursome handshake all around. "You got this, Sam." "You're the best." "Clare's our only hope for you to pull this off."

The night of the costume contest, Jake, Robbie, and Teddy showed up at my house. They were already dressed as the Tin Man, Scarecrow, and Cowardly Lion. Their costumes were expensive and professional grade, not some cheesy off-the-rack stuff for $39.99. Clare let them into the living room, I was still in the bathroom. "Dorothy, come on out. Your heroes are here." She was giggling the whole time she said this.

Clare can be such a b*tch sometimes; I say that with all the brotherly love I have for her. I'd made the mistake of letting her order my costume and she had decided I was going to be the sexiest Dorothy ever! My dress had the same blue and white gingham pattern but that was about the only similarity.

It was shoulder less and strapless, with a deep plunging neckline that wouldn't allow me to wear a bra and left my ample decolletage easily visible. The skirt didn't even come down to mid-thigh; I was afraid if I bent over my ass would be on full display. I was wearing a white lace garter belt and matching thong. The garter belt had eight straps and held up the sheerest white nylons with back seams and lace tops. Any movement by me and the skirt rode up enough you could see the garter tabs clipped to my stockings. As for the ruby slippers? Clair had chosen ruby sequined stilettos with open toes and 4 1/2" heels.

She'd done my makeup in ruby tones that matched my shoes. Ruby chrome nail polish on my fingers and toes, ruby glitter lip gloss, and an overall ruby palette for my eyes and cheeks. She'd added some auburn toned highlights to my hair as a nod to Judy Garland and tied ruby red ribbons around my two pigtails.

Even though Dorothy hadn't worn any jewelry in the movie, Clare had purchased a faux white pearl jewelry set. It consisted of a single strand necklace, pearl dot earrings, and four pearl rings which I wore on the pinky and index fingers of my left hand, and the middle and ring fingers of my right hand. Finally, I was holding Dorothy's basket with the stuffed animal version of Toto.

"Dorothy." Clare called. "Don't keep the boys waiting. You mustn't be late for the contest!"

I took a deep breath and looked in the mirror. If the Wizard of Oz had been shot as a porn movie, I would have been perfect for the lead role! I sighed, and walked into the living room, dreading what was soon going to follow.