This story contains very graphic sexual language and situations. If you are under 18, or offended by boys who dress up and have sex with other boys, please stop now.
Best Girlfriends
by Angela Stevens
For the last few weeks I've been going out with Lisa. She's the most beautiful girlfriend I've ever had. I thought everything was going well, and we were developing a real relationship. One that would last. I guess I must not have let Lisa know how I felt, though. I'm kind of shy, and it takes me a long time to get physical with a girl. Most of my previous girlfriends actually ended up making the first move themselves after they got horny enough. Lisa, however, is a psychiatrist. Instead of just grabbing me and kissing me, she wanted to talk. When I drove up to her house to drop her off after an evening of dancing she took me by the hand.
"Honey, is there something wrong with me?" She asked, "We've been going out for a month and you haven't even tried to kiss me! Don't you like me?"
I could see hurt and insecurity in her face. I felt so bad for making her think I didn't like her. "Of course I like you, Lisa." I replied. "I didn't mean to make you unhappy. Please forgive me."
Lisa put on her professional face and voice. "You know, Philip, you've been acting like one of my girlfriends instead of my lover. I'm a psychiatrist, and I know just how to deal with this problem. I want you to be my lover, not just my friend. Will you let me give you some therapy tonight? No charge?"
I was eager to please her. "Yes, of course, Lisa. Let's try." I answered.
She leaned over to kiss me, and when our lips met and parted she forced her tongue down my throat, just the way a man is supposed to do to a woman. "Oh, well." I thought. "I guess since she made the move she's got a right to be aggressive." She slid her tongue in and out of my mouth for a full minute before coming up for air. I could taste and smell her lipstick all over my mouth. She took my hand and led me up to her apartment.
"The way this therapy works is that I have to turn you into what you don't want to be, so I can teach you how to be what you do want to be. OK?" Lisa said after we were inside. "Go take a hot bath. With bubbles." She pointed me in the direction of the bathroom.
The bubble bath had a very flowery smell, but it did make the water seem silkier. After I'd slid beneath the foam Lisa knocked gently and then poked her head in the door. "Can I come in, honey?" She asked. I nodded my head.
"Good. Let's get started. Lay back and relax, Philip. Close your eyes." She instructed me.
I floated in the hot water, imagining I was on a perfumed cloud.
Lisa continued to talk in a soft low voice. "Forget everything except my words. You're in another world, and you're becoming another person. Feel your legs. Think how nice they'll feel when we get rid of all that nasty hair. Hair is OK for boys, Philip, but you're becoming a nice, soft girl now. Your skin is so soft, lift your leg out and let me rub some cream on."
I felt myself doing as she instructed. It felt so good to have her rubbing my leg.
"Now keep still while I make your leg as smooth and pretty as you want it to be." She said sweetly.
I felt the razor gliding up and down my leg. I was happy to know my leg would soon be smooth and pretty. Lisa finished the right leg and continued with the left.
"You have such nice, shapely legs, Philip. They're going to look so nice in your sheer black stockings. With sexy high heels, too. You're going to have real centerfold legs." She continued as she finished shaving my left leg. She gently lifted my arm out of the water. "A pretty girl can't have all this hair under her arms, either." She shaved it clean. Then she had me sit up so she could do the other one.
"This hair around your boobies has to go, too. Let's make you so smooth there so your bra will fit right."
I happily let her shave my chest, looking forward to how much better my bra would feel against smooth skin.
"You're being such a darling, Philip. Lean back and let me wash your hair." She said.
I was happy that I kept my hair long. Her fingers felt so sensual as they massaged the shampoo in.
She rinsed the soap from my hair with fresh, warm water from the tap. "Sit still for a second, Hon, while I even out these bangs." She said. I closed my eyes as she combed my clean hair forward, then felt the scissors go snipping across my forehead.
"Now that your hair is out of the way, I can see we need to even out those eyebrows a little. This may hurt, but be a brave girl and let me make you even more beautiful."
My brows must have really been bushy, because she spent at least ten minutes with the tweezers, plucking hair after hair. I knew the pain was worth it if it would really make me more beautiful.
"Now lay back and sleep for a sec while I get a few things from my bedroom. You're just going to love the sexy things I bought you. Let your body relax completely while I'm gone."
I woke up when she came back.
"You're so soft and smooth now Philip! Even if this wasn't therapy, you'd like it, wouldn't you? Well actually, since you're going to be my girlfriend tonight, you have to be smooth like that. I certainly don't have any hairy girlfriends!" She laughed.
"It's time for us to pick a more feminine name for you. Didn't you say your mother's name was Angela?" Lisa asked me. I nodded my head. "Good, Angela is the perfect name for you now, my perfect little angel. Get out of the tub now, Angela honey, and let's get you dressed."
She dried me off with a big, soft towel, and patted sweet smelling powder all over my body. When she had finished she reached over to the counter and picked up a lacy pink bra. She held it out, with the silky cups toward me.
"Here, Angela, let me help you with your bra." She said.
I stepped forward to put my arms through the straps, and then turned around so she could fasten the hooks in the back. I looked down at large, empty cups.
Lisa saw me looking, and returned to the counter. "Don't worry, sweetie, I thought of that too. Come here and let me help you fill your figure out."
She slid a very large pair of silicon forms into my bra, and then adjusted the straps so they were properly supported. She giggled. "You're even bigger than me now! You're going to get so much attention from the boys tonight. I'm getting jealous!"
She had me sit down to pee, then helped me into a pair of pink lace panties that matched my bra. We finished off the undergarments with sheer, black pantyhose. They felt as silky going up my smooth legs as she had promised they would.
In the bedroom, she handed me a soft, pink sweater that nicely accented my large breasts. After I put on a short, tight, black skirt, she had me sit in front of the vanity table while she braided my long, blonde hair up into a fancy knot in the back. A pink scrunchy that matched my sweater held the braid in place. Then she produced a set of long, red fingernails, and used super glue to attach them. My fingers looked so long and sexy with the long nails!
Mascara and eye-liner went on my eyes, underneath my high, thin eyebrows. Blush made my cheeks nice and pink. Bright, red lipstick completed the transformation. Lisa handed me a pair of high, black heels. With a few more suggestions she had me walking like a pro.
"Your purse is there on the bed, Angela." She stated. "What do you say we go out and see how much trouble two sexy babes can get into in this town?"
I checked myself out in the mirror by the door before we left. I could never remember being prettier than I was right then. I practiced licking my lips to put a shine on my lipstick. Somehow I knew I'd be licking my lips later that night.
She drove me to a seedy bar on the outskirts of town. There was a line of big black motorcycles parked in the gravel lot. "Welcome to Luckys, Angela. I used to be a regular here before I met you. You're gonna like my friends. They're gonna like you too, sweetie!"
As soon as we went through the doors the men descended on Lisa and me. I felt like a turkey drumstick at a banquet of barbarians. When we had fought our way to a table at the back I just wanted to sit and collect my thoughts. I was annoyed when a tall, muscular man came up and demanded a dance. Lisa saw my anger rising and cut me off before I could answer. She whispered in my ear: "Don't be such a bitch, Angela, dance with him. You're such a little cock-tease!" She pushed me toward the dance floor.
I decided what the hell. I might as well give the big buffoon a thrill. He held me tight as we swayed to the music, stroking the crack of my ass. I have to admit I felt very protected in his arms. I could tell from his hand on my butt that he wanted me, and it gave me a feeling of power that I wasn't used to. Just as I began to appreciate the size of his broad, muscled chest, the music ended. I turned to go back to the table but he caught me by the arm. His other hand went to the back of my head and pulled my lips to his. His hot tongue licked my lips and then slid between them, filling my mouth. The sensation was like nothing I'd ever felt before. My whole being focused on his kiss, which seemed to last an eternity. When he pulled back I felt lost and confused as I made my way back to Lisa.
Lisa had seen the whole thing, and she got up to hug me. "That was such a sexy kiss you gave him, Angela. If you were really my girlfriend I'd be jealous of you! You really turned him on. Go ask him to come sit with us."
I didn't need to move, except to look at him. His eyes met mine and he picked up his beer and joined us. Lisa was on one side of me, and Deke (that was his name) sat on the other. After a few minutes of small talk he looked into my eyes and kissed me again. This time it wasn't such a shock. I quickly began to enjoy it again, and my shy tongue played little games with his. When Lisa took my hand and put it on his crotch I could tell she was right about how turned on he was.
She whispered in one ear while Deke's tongue cleaned the other. "Take his dick out and stroke it for him, you silly girl. You can't leave him all hot like this. He might rape somebody. Do it now, honey. You don't want to make him mad, do you?"
I definitely didn't want to make him mad. I didn't want him to stop kissing me, either. He groaned into my mouth as I reached in his pants and took hold of his cock. He squeezed my breasts as Lisa guided my hand, sliding the smooth skin up and down on his hard flesh. When he came both our hands were soaked with his milky white juice. Lisa held hers up to my lips.
"Good job, honey. Have a little taste." She said as she poked her finger into my mouth. "Pretty good, huh? You can see why I like this place!"
I sucked her finger clean, savoring the strange spicy taste.
"Here's a napkin, Angela. Wipe your hand off and let's go home."
When we returned to her apartment and went inside, Lisa took me by the hand. "Angela, come to the bedroom. I have a surprise for you!" She said.
I was pleasantly surprised to find another big, handsome man on Lisa's bed. I was fresh from my first kisses with a real man, and fluttered inside when I thought about kissing this one.
"Angela, this is Michael. He's a colleague of mine, and a registered sex therapist. I invited him over for a little role-playing exercise we need to do. You don't mind, do you?" Asked Lisa. She didn't wait for my answer. "No, of course not. You can't wait to get your hands on him. Michael, stand up and let Angela undress you." She directed.
Michael stood in front of me. I sat on the edge of the bed and unbuttoned his shirt, then slipped it from his shoulders and down his arms. His hard, lean chest made my mouth water. I put my hands on his waist and unbuckled his belt. Then I opened his fly and pulled his pants down. His big, soft, dark cock was inches from my face as I got down on my knees to untie his shoes.
When he stood naked before me Lisa asked, "What do you think of his cock, Angela? Look at it closely and describe it for me." She directed.
"It's big and dark." I said. "Much bigger than mine and much darker than the rest of him. There are veins in the shaft, and the head is kind of purple."
"Touch it, and tell me how it feels.", she ordered.
I reached out and wrapped my hand around it. "The skin is smooth and loose," I said. I began to slide back and forth. "I think it's getting bigger now." I kept stroking. "Harder, too. It's enormous!" I gushed. My eyes were glued to the manhood that stood erect in front of my face.
"Smell it." Lisa told me.
I leaned forward and sniffed the musky scent. "I smells wonderful. So deep and sexy." I said as my hands continued to fondle the huge cock.
"Don't be afraid, Angela. Kiss it."
I softened my red lips and gently kissed the fat knob on the end, leaving pretty lipstick smudges. The skin was so soft and velvety. I didn't wait for Lisa's next instruction before my lips parted and I began to lick and caress it with my tongue.
"That's right. Lick it and see how it tastes. Suck that cock. Feel it get bigger in your mouth!" She whispered excitedly. Then she put her hand on the back of my head and pushed me forward, forcing Michael's cock deeper into my mouth, up against my throat. I began to gag, and Lisa let me pull off to breathe. Then she pushed down again. She found a rhythm and kept pushing me forward, then pulling me back. Each time the cock went a little further down my throat. "Tilt your chin forward, sweetie. That's right. Now swallow. Relax and swallow. I won't let it hurt you." She said as she pushed forward. Once the fat head of the cock passed into my throat it was easy for the rest to follow. My lips came up against Michael's pubic hair and balls. When there was no more resistance from me Lisa let me find my own tempo. I continued bobbing my head up and down, each time up sliding the head out past my lips, and each time down bringing my nose back into his fragrant, curly pubic hair.
"When he starts to squirt, be sure to taste and swallow every drop. You're going to have to write about it in a journal for your therapy." Lisa must have been watching Michael closely, because just then he started to come, his dick rippling in my mouth as he held my head and shot load after load of sperm down my throat. When he pulled slowly out I looked up into his eyes. I smacked my lips and a little come drooled down my chin. I kept his gaze as I used a finger to scoop it back inside. I swished it around and then swallowed.
Lisa was pleased. "Angela, you're such a hot bitch! I think it's time for me to strap on a dick and fuck your sexy ass. Come bend over the edge of the bed. Give me your sweet cherry, Angie. I promise you'll love having your ass full of cock. You'll be just like a real girl!" She said.While I was occupied with Michael's cock she had strapped on a large, clear plastic cock in a black leather harness. I bent over, squeezed a pillow in my hands, and bit down on my lip to ease the pain. Lisa began to force the dildo up my ass. I squealed when she penetrated me, then continued to moan as she slid in and out, each time taking it all the way out so she could push through my tight hole again. I loosened up and relaxed in a little while. The pain subsided and I found that I enjoyed the new sensations in my ass. My moans of pain changed into moans of ecstasy. My little penis was painfully erect and I pushed back to meet her thrusts.
"I think she's loose enough for you now, Michael. Whenever you're ready." Lisa said.
She pulled out and Michael walked up to me. He made me turn over so I could watch. He lifted my legs up and I rested my high heels on his shoulders. I screamed as the head of his cock slid up my butt. The dildo had been minuscule compared to the meat that pounded me now. In the middle of the pain, Lisa reached down and began to jerk me off while Michael fucked my ass. When I heard him moan and felt a spray of hot liquid inside, Lisa gave me a few quick strokes and brought me to orgasm. She held out a glass and caught my sperm. "We can't have any spots on the bedspread." She said with a smile.
Michael pulled out and I collapsed back on the bed, quivering with delight.
Then Lisa snapped her fingers. I suddenly realized what I'd spent the night doing.
"You know we filmed that, don't you Angela? I've got some news for you. From now on, if you don't do exactly what Michael or I say, that tape is going to show up in a few very embarrassing places. Like your bosses mailbox, or your mothers. Mommie would be very disappointed in her little sissy boy who borrowed her name, don't you think?" She teased.
"In case you haven't figured it out, Michael is no therapist. He's actually my new boyfriend." She admitted. "He was getting jealous of all the time I spend with you. He told me to dump you, but I just couldn't bear losing you. So we reached a compromise. If I could turn you into my sissy girlfriend, I could keep seeing you. Only when you're dressed as a girl, of course. And Michael just loves to fuck pretty girls like you in the ass. I don't really like it when he does it to me, but you seem to enjoy it a great deal. So it's a win-win situation, isn't it sweetie?"
"I have to admit you make a much prettier girl than I thought. You suck cock like a pro, too. Are you sure you haven't had any practice at that?" She teased. "Well, you'll get lots from here on out. Tomorrow night Michael's friend Stan is going to double date with us."
She went to her doctor's bag and pulled out a large syringe. "I've cooked up a little prescription for you honey. A gynecologist friend of mine said this is just the stuff you need to help grow some nice tits of your own."
She injected me in the ass and under each nipple.
"Oh, Angela! Once you've got a pair of big boobs of your own, we'll find lots of nice boys to suck them for you. We're going to be such good girlfriends! Relax for a few minutes now and enjoy a nice protein drink." She said as she handed me the glass of my own juice.
"Don't miss a drop Angela. It's too precious to waste!"
The End