Practice Makes Pervert free porn video

Practice Makes Pervert By David Terry Terry had spent the day trying to come up with a solution to the problem that he shared with his best friend Dave. They were seventeen and still virgins. The evening before they had talked for hours about how they had ended up this way and what to do about it. Dave felt that it was mostly a problem of opportunity. The two of them were not members of any of the social clinics at school. They were not nerdy enough to be geeks, to small to be jocks and their average looks meant that girls paid them little or no attention. He was sure that if they belonged to one group or another then they would have the chance to score. Terry thought it was more than that. He had brought up the fact that even if they had the chance; they did not have any experience with girls and would probably screw up. The conclusion was that they needed the experience to capitalize on the opportunity, but how were they to get experience without the opportunity? It was a classic catch twenty-two. The last thing that Dave had said before going home was that it was a shame one of them wasn't a girl, that way they could create the opportunity and get experience any time they wanted. It was that thought that had been rattling around in Terry's head all day. What would happen if one of them pretended to be a girl? Terry knew that the idea was strange, but logistically it would work. His parents were leaving in three days for a month in Europe, his twenty-year-old sister had moved out several months before so there would be no one home and summer vacation was just beginning. But Terry and Dave knew so little about girls, how could they impersonate one? That of course that was the crux of the problem. No experience with girls. Perhaps if one of them pretended to be a girl they could examine things from both points of view and figure out some of the mysteries. Terry and Dave had been friends since the first grade and he did not want to do anything that might mess that up. The more he turned the idea over in his mind, the dumber it sounded, yet there was something wicked about it and he could not get it out of his head. Before suggesting his idea to Dave, Terry decided to do a little experimenting alone. The day after his parent's left; Terry went into his sister's old room. Poking around the closets and drawers he discovered that Karen must have left half of her stuff behind. The closet was full of dresses, blouses and skirts, with at least a dozen pair of shoes on the floor. The top drawer of the dresser was a colorful array of silky panties and bras. The second drawer held hosiery and lacey teddies, the third, slips and nightgowns, while the bottom drawer held things like shorts and tops and jeans. Running his hands over the soft garments caused his cock to harden. These were the very items that he and Dave desperately wanted to see and feel. Of course they wanted to feel them on a hot girl, but even folded in the drawers they were exciting. That made his mind up. Dave had a part time job during the afternoons. Terry knew that he had at least five or six hours before Dave would call to see what the plans were for the evening. He went to his own room, stripped off his clothes and dumped them on the bed. Sitting naked at his desk, he made a detailed list of all the things he imagined a girl would do before going out on a date. The list was longer than he would have thought and still Terry was sure he had forgotten some things. Returning to his sister's room he did the first thing on the list. He turned on the water in the tub and added a generous amount of bubble bath. Terry had never taken a bubble bath before and as the tub filled, the delicate smell of the scented water reached his nose. Looking at himself n the mirror he saw his cock, swollen and hard. Settling back in the tub, Terry reviewed the list. Shave, wash and blow dry hair, paint nails, find a nice outfit, decide on shoes, etc. A lot to do. Very carefully Terry shaved the light hair off his legs and chest, then the darker hair from under his arms. After shampooing his almost shoulder length hair Terry relaxed in the hot water and began to caress his hairless legs and chest. He noticed how smooth and sexy they felt to his hands. Closing his eyes and pretending that he was touching one of the hot girls at school, his very stiff cock jerked as his hand passed over his nipples and they hardened into tiny points. After climbing out of the tub, Terry wrapped his hair in a towel turban style like he had seen his sister do many times. Placing another towel around his waist he again looked in the mirror. Something was wrong. It took him a minute to figure out that a girl would wrap the second towel just above her breasts, not around her waist. After making the adjustment his reflection now showed a thin, plain looking person whose gender could be male or female. Searching around the bathroom drawers and cabinets he found the next items on the list. Nail polish and as importantly, nail polish remover. Faced with a choice of light pink or dark red, Terry chose the red. Sitting down at the vanity he decided to do his toes first. That would give him at least a little practice before he colored his fingernails. Surprisingly it was not as difficult as he would have thought. The years of hand painting model cars and planes paid off and he was done with his hands and feet quickly. The once neutral reflection in the mirror was now definitely becoming female. The sight of his red nails against the white towel around his chest was very exciting. He carefully dropped the towel and being cautious of his wet nails, slowly traced his fingertips down his chest and belly until his fingers were massaging his throbbing prick. Pretending that the hand of a pretty girl encircled his hard cock was easy. After only two strokes his cock exploded, sending a long stream of cum up and out. Terry was drained. He had been jerking off for a couple of years but he had never cum that hard. He quickly cleaned up the mess, wrapped the towel around him again and began to search the bathroom for any make up his sister might have left behind. In one of the drawers he found several tubes of lipstick, a little compact that had four different colors of eye shadow and a mascara pen. Not knowing how any of this stuff worked he carried the items into the bedroom to read the minimal instructions on the make up while his nails dried completely. By the time his nails had dried he was confident that he could handle the make up. Returning to the bathroom he very lightly applied a blue eye shadow. The mascara pen was next and again he barely touched his lashes, adding thickness a little at a time. Although it was not perfect, Terry was pleased with the results. Slightly longer, thicker lashes and a subtle light blue shading above and below his eyes. Deciding to leave the lipstick until later, he shook his damp hair free of the towel went to the dresser to find things to wear. Upon opening the top drawer of his sister Karen's dresser, Terry was amazed at the different styles and colors of the items that she had left behind. He wondered what she had taken with her if this was what was leftover. He picked the panties up and examined them one at a time. What would a teenage girl wear on her first date with a boy? The thought that this was indeed a date made his cock start to harden again. Following the thought train in his head, Terry realized that despite the fact that he and Dave talked about girls all the time, this was the first time either one of them had ever been on a date. He chose a full cut, dark blue nylon panty because he did not want to get his man too horny, too quickly. Giggling to himself, he found a bra of very similar color that had push up pads and lots of lace on the cups. After dropping the towel from around his chest, Terry shuddered as the panty slid easily up his shaved legs. By the time he had settled the panty comfortably around his hips, his cock was fully erect. His ass was held snugly and at the same time, softly by the silky panty. His cock, completely encased in the cool nylon, tented the front a little. The bra was tricky until he figured out how to clasp it in front of his belly then turn it around and pull it up to his chest. Placing his arms through the straps and drawing them up his shoulders caused the bra to tighten against his nonexistent tits. The padded cups helped give him small breasts but Terry knew that the bra was not fitting properly. After removing it and adjusting the straps several times, he managed to get the cups centered over his nipples, which were so hard that they ached a bit. The constriction on his chest from the bra felt odd, but nice. Terry shivered as he realized he liked the sexy feel of his sister's lingerie holding, squeezing and caressing his young male body. According to the list, Terry was supposed to blow dry and then brush his hair next. The strange feeling of a bra around his chest made him realize that other things were going to feel strange also. Like wearing shoes with a heel. It occurred to him that he could get a little practice in heels if he wore them while drying his hair. If he were going to wear heels, he would need to wear hose with them. Closing the top drawer of the dresser, Terry pulled open the second one. The left side of the drawer had four garter belts, the center held an assortment of stockings and pantyhose and the right side, a stack of silky teddies. Picking the top garter belt from the pile, Terry unfolded it. It was made of see though white lace and fully six inches tall. The only part of it that was opaque, were six stiff stays, designed to hold it in place and trim the wearer's waist a bit. Terry could see two more belts, one black and one bright pink; both in a shiny satin material still in the drawer. Before he could reach in and pull out the fourth belt, one that appeared to be much taller than the others, he decided that as exciting as wearing a garter belt and stockings would be, he should not choose them for a first date. Placing the white one back, he located a pair of tan pantyhose, closed the drawer and went to sit on the edge of the bed. As he sat down, the head of his still hard cock slid out of the top of the panties, leaving a wet trail of pre-cum on his belly. Wiping the fluid from his belly and the head of his cock with a finger, he instinctively placed that finger in his mouth, cleaning it with his tongue and lips. The warm pre-cum was slightly oily and although it tasted different than anything he had had before, Terry did not think it was too bad. The pantyhose took less time to figure out than the bra had. Terry thought it was a lot like putting on really long athletic tube socks. Bunching them up at his feet, he rolled and slid and wiggled them up his calves, stopping at the knee to line up his toes with the little front seams and adjust the heel. From there it was just matter of smoothing them up over his thighs and centering the seam between his legs. Finally getting them comfortably in place, Terry walked to the closet to find shoes. The sensation of the pantyhose holding the snug panties even tighter to his cock and the firm way they massaged his ass cheeks was almost more than Terry could stand. He decided it was a good thing he had chosen pantyhose because they would keep Dave from knowing exactly how excited he was. Plus, if Dave did get fresh, the pantyhose would make it more difficult for him to take advantage of Terry. If he did let Dave get past first or second base, Terry wondered if Dave's pre-cum would taste the same as his own. Blushing, Terry opened the closet. Before checking out the shoes on the floor, Terry decided to pick a dress. Almost immediately he saw what he wanted. A light cream colored summer dress, that when his sister wore it, fell to just above her knees. Terry thought the material was not quite thin enough to see through but would allow Dave to notice the dark outline of his bra. Choosing the dress made picking out the shoes a snap. His sister always wore the same pair of three inch heeled, off white, strappy sandals with this dress. Glancing down, Terry was delighted to see them on the floor. Leaving the dress on the hanger for the moment, Terry slid his left foot into the sandal. Gently pulling the elastic back strap up behind his heel, he was pleased that his red toenails were visible through the open toes. Quickly sliding the other shoe on, he took the dress and headed for the bathroom. Carefully placing the dress hanger over the top of the open door, Terry looked at himself in the mirror. He was thrilled with the change. Gone was the once gender neutral image. In its place was a budding although plain looking teenage girl. His legs looked long and slender, his butt although not as full and round as a girl's had a nice curve to it and the dark blue bra held a promise of small breasts. The light make up made him look like a sixteen year old attempting to look older and his damp, uncombed hair was wild and sexy. Fighting the urge to stroke himself, Terry began blow drying his hair. Fifteen minutes later he was done. Drying your hair as a girl or boy was the same. The only difference was that when he was finished, he parted it in the center, swept back both sides and pinned it behind his ears with a pair of barrettes he found in the vanity. Just as he finished fluffing out his bangs, the phone rang. Hurrying in the unfamiliar heels Terry over balanced and almost fell. Forcing himself to slow down, he was nonetheless breathless when he answered the phone. It was Dave. "Hey, what's going on?" Asked Dave. "Well, nothing, you know." Responded Terry as he tried to gather his thoughts. "Why do you sound funny, like you are out of breath or something?" "I was running to get the phone, I didn't want you to think I was out or something." Replied Terry, trying to get his breathing to return to normal. "Yeah, like you got anywhere to be." Wisecracked Dave. "What's up for tonight, same old stuff?" "I thought we could watch a movie or something. Maybe get pizza." "It's not like we got anything else going on. Okay it's a date." Said Dave. "A date?" What do you mean?" Terry barely whispered his heart pounding. "I mean it's the first Friday night of the summer and I'm spending it with you. Not that I'm complaining, but I would rather be with a hot chick, preferably one with low morals." Laughed Dave. "Well sailor, you never know. You might get lucky." Answered Terry in as soft and feminine a voice as he could. Dave laughed again. "Keep talking like that and you may get lucky!" He exclaimed. "I'll see you around seven." Terry hung up the phone, his heart still beating hard. Calming himself down, he realized that seven o'clock was only fifteen minutes away. Returning to the bathroom Terry removed the dress from the hanger and ignoring his very erect cock being held back by the panties and hose, he undid the four buttons that held the top of the dress together. Holding it open at the shoulders he stepped into the dress, drawing the soft material up his body. Slipping his arms through the half sleeves, Terry adjusted the shoulders and hooked the four small buttons into their loops. He was surprised and pleased to see that the dress rode higher on him than it did on his sister. It was fully four inches above his knees, almost a mini dress. With only a few minutes remaining, Terry opened the red lipstick and carefully applied it to his lips. Terry did not know about blotting his lips on a tissue but the strange slickness of the lipstick caused him to rub his lips together, which smoothed the gloss pretty evenly across his lips. Looking at himself in the mirror, Terry barely had time to wonder where all his brains had disappeared to, when he heard Dave knock on the front door. Shouting for him to come in, Terry took a deep breath and prayed that he was not about to destroy his friendship with Dave. From the living room Dave yelled, "Terry, where are you man?" Terry tugged at his dress nervously then stepped from the bathroom into his sister's room. "Are you ready sailor?" He called back. Terry could here the laughter in Dave's voice as he replied, "I told you to quit talking like that, I'm ready for anything!" Mentally crossing his fingers Terry stepped slowly into the living room. "Ready even for this?" He whispered. Dave turned at the sound of Terry's voice. "Ready for any..." Was as far as Dave got before his mouth dropped open in shock. "Terry?" Nervously Terry chewed his lower lip and nodded. "What, I mean where did you get, how did you." Dave trailed off. In a rush of words Terry tried to explain his thoughts and actions leading up to this moment, ending with his desire not to have ruined their friendship and the offer to go change and forget the whole thing. "No." said Dave. "Don't change. You look great. I was just surprised. And of course we are still friends, I mean whom else but a friend would go through this? It takes balls. You still got balls, right?" He added smiling. "Yes I do, although they are pressed pretty tightly inside the panties and pantyhose." Said Terry, finally exhaling a breath he had not realized he was holding. "Panties too? Turn around and let me see all of you." Dave asked, with a little tremor in his voice. Slowly Terry turned. When he had turned all the way back around, he saw that Dave was staring at his legs. "You have a great ass. I can't believe I just said that. UM, how does it feel? You know, wearing all that stuff?" Asked Dave. "It excites me." Terry responded honestly and simply. "Me too." Added Dave. "I know." Said Terry, looking at the obvious bulge in the front of Dave's jean shorts. Embarrassed, Dave said, "So what do we do now?" "Well we watch the movie I guess, and no getting fresh. This is our first date!" Laughed Terry, trying to break the tension. "You pick out a movie and I'll make popcorn." Turning on his heels, Terry went to the kitchen. Dave's gaze followed the sway of Terry's ass until he was out of sight. While Terry was in the kitchen, Dave tried to pick a movie while sorting the thoughts in his head. Terry sure looked hot, if that was the right word, not quite like a girl, his moves weren't smooth enough, but what a good figure he had. He was surprised by the hard on in his shorts. Was he gay? No, then why did the sight of his best friend dressed up as a girl make him excited? Two thoughts occurred to him. One, if Terry would go this far, he might go further and Dave could have some sex. He had never come close to having sex with anyone and even though it was a guy, well, weird sex was better than no sex. And Terry was his friend, what ever happened, no one would find out. His second thought, coming quickly on the heels of the first was that a boy, wearing lingerie and heels and stuff was naughty and sexy somehow. It gave Dave a hard-on; there was no arguing that. As Terry returned with the popcorn, fresh from the microwave, Dave hastily grabbed a movie, placed it in the machine and headed to the couch. Terry placed the bowl of popcorn on the table and sat on the couch about a foot away from Dave, being careful to smooth his dress under his legs and to sit with his knees touching. The movie began and the two of them sat quietly on the couch, both lost in their own thoughts, both with straining erections and both wondering what to do now. After about thirty minutes, Terry decided to make the first move. Squealing at a well-timed moment and pretending to be frightened by a scary part in the film, he scooted over towards Dave, burying his face in his neck. Dave automatically placed his arm behind Terry's shoulders and gave him a hug. They sat like that for another hour, until almost the end of the movie. Then it was Dave's turn to make a move. The bowl of popcorn had been moved to a space that shared both of their laps. It had been acting as a kind of safety fence. Dave picked it up and placed it back on the table, returning his right hand to where the bowl had been; on his own thigh, very close to Terry's. After a moment, Terry felt rather than heard Dave take a deep breath and then watched as his hand crept slowly across the small space between them and onto Terry's thigh, just above the hem of his dress. Terry let out a small sigh that he hoped was encouraging and snuggled a little closer. Dave did indeed take it as a go ahead and a moment later started gently squeezing Terry's leg through the thin material. Terry could not believe the emotions going through him. Here he was wearing his sister's clothes, in the arms of and being fondled by his best friend. Instead of being disgusted with himself, he was aroused. He could feel his small nipples hard and rubbing against the soft roughness of the bra and his cock was rigid in the tight confines of his panties. A glance at his friend's lap told Terry that Dave was excited as well. Rolling slightly to his right and tilting his head a bit, Terry placed his hand over Dave's tented crotch, squeezed it gently, closed his eyes and waited to be kissed. Dave might have cum from the unexpected pressure on his cock if he had not been so surprised by Terry's move. Looking down into the face of his friend, he realized that Terry was wearing make up. Although part of him must have known this, from this close Dave could see that the soft blue around the eyes had small sparkles. He watched as Terry's tongue nervously wet his red lips and finally, almost involuntarily, Dave's own lips followed that captivating tongue back into Terry's mouth. Kissing being new to both of them they were shy at first. Slowly they began moving their mouths, lips brushing at first softly and then with more urgency. Dave ran his tongue into Terry's mouth, the feeling of it sliding through the slick lipstick causing him to gasp. As Dave grew bolder, his tongue penetrated deeper into Terry's mouth. Pursing his lips, Terry sucked the tongue as far in as he could get it. Sensing his friend's need, Dave stopped moving his tongue and left it fully extended inside Terry's mouth. Terry sucked hungrily the inch and a half of offered tongue. Enclosing it with his lips he moved his face in and out. He alternated between playing the underside of his tongue against the very tip and circling the entire thing with his own tongue. It was like sucking a small cock Terry imagined. That thought was more than his over excited cock could take. Terry's body stiffened and his cock exploded for the second time in less than three hours. The kiss, the movie and Terry's orgasm all ended at the same time. Dave, hearing his friend's moan and then feeling him stiffen against his thigh, whispered, "What happened, did you cum?" Terry merely groaned softly in his throat, which Dave took to mean yes. They sat that way for a while, Terry contentedly rubbing and squeezing Dave's cock through his pants and Dave amazed that his friend could cum without being touched. Finally Terry opened his eyes and said to Dave, "I'm sorry, I did not mean to stop. I already came once today while I was getting dressed and I thought that was a hard cum. But this last one was incredible." "You came from getting dressed?" "Yes, it was exciting. I couldn't help it. But now I have come twice and you haven't at all. Do you want me to finish you off?" Replied Terry mischievously, giving his dick a harder squeeze. Before Dave could answer, Terry was undoing his belt. "What are you doing Terry?" He whispered. "Why taking out your cock of course. I thought you might like to see my red fingernails pumping that big piece of meat your hiding. Besides when you cum for me you don't want to cum in your pants do you?" Terry responded with a smile. Not giving Dave time to respond, Terry finished with the belt and easily unsnapped the top of Dave's shorts. "Stand up Dave, make it easier for me." Breathed Terry. Dave stood and Terry placed his hands on either side of his hips and together with his underwear, slowly pulled Dave's shorts down to his ankles. Terry did not see Dave's cock pop fully erect out of his pants because the whole time he was pulling them down; he was starring in Dave's eyes. "Oh, very nice." Said Terry as he finally looked at the six inch, very hard cock directly in front of his face. Dave could only stare as he looked down and saw Terry kneeling in front of him, his aching cock inches from his friend's mouth. "Um, Terry?" "Yes Dave." "Do you think, I mean instead of a hand job, could you um, you know..." In answer, Terry leaned forward and touched the soft head of Dave's cock with his tongue. "Do you want me to blow you Dave?" He asked. "Yes." Answered Dave softly. "I will, but you have to understand that anything I do to you tonight, you have to do to me tomorrow night, when I dress you as Cindy. Do you still want me to suck your cock until you cum Dave?" "Cindy?" Said Dave with a far away look in his eyes. "Yes Dave, Cindy. If I blow you will Cindy blow me tomorrow night?" Asked Terry as he again reached out with his tongue, swabbing it roughly over the underside of Dave's hot cock. "Yes, Cindy will do anything you want Terry." "Anything?" "Yes, anything. Please suck me." "Sit back down then and let me show you what Cindy has to look forward to." Said Terry, rubbing the silky material of his dress against Dave's cock as he rose from his knees. Dave sat and watched as Terry stepped in front of the television. Slowly and with as much camp as he could muster, Terry undid the top of his dress. Button by button the dress came open, revealing the dark blue lacy bra underneath. Sliding his arms out of the sleeves Terry let the dress slip to the floor. Standing in just his bra and panties, stockings and heels, Terry began to rub his small breasts through the bra. Turning around so that Dave could clearly see the outline of his panties through the hose, Terry began to rub his ass. Moving forward Terry slipped to his knees and as he lowered his head towards Dave's throbbing cock said, "I have an even sexier outfit for Cindy to wear. You are going to look so great as you do this to my cock." With that, Terry sucked Dave into his mouth. Ignoring the gasp that came from Dave, Terry slid the first two inches of cock between his lips and stopped. Dave's cock was hot in his mouth. He could feel the hardness of the shaft behind the softness of the smooth head. The veins pulsing with blood. Not sure how much of Dave's cock he could take, Terry pulled back until just the head was in his mouth. Taking his tongue and rubbing lightly over the softer underside produced a moan from Dave. Terry reached up and grasped the shaft with his right hand and slowly began to pump Dave's cock. He pulled back to the very end of Dave's cock and slipped his tongue lightly into Dave's pee hole and then took his mouth off it altogether. Looking up he saw Dave's eyes were closed. "Am I doing okay?" Asked Terry. Dave opened his eyes, looked down and saw Terry, his red lips an inch away from his dick, his brightly painted fingernails holding his cock at the base and was barely able to say... "Great. I don't know how much more I can take." "Good," responded Terry, "I want you to cum. I want you to cum in my mouth. I am going to suck as much of your cock into my mouth as I can and I am going to make you cum. But don't close your eyes, I want you to watch me swallow your cock and your cum." Dave's breath came even quicker as he listened to his friend's words. They locked eyes as Terry took first the head and then four more inches of his cock into his mouth. Firmly griping the base of Dave's cock, Terry slid quickly up and down the now tight skin. He knew it would only be a minute before Dave came in his mouth. And he wanted him to. He wanted to feel the hot cum shooting onto his tongue. He needed to make his man cum. Terry felt the tremors in Dave's cock and knew he was about to get his first taste of cum. Without taking his eyes from Dave's, he pulled back and began to suck and lick the head only, pumping Dave's shaft with his fist. Dave's hips rose off the couch, instinctively trying to get more of his cock in Terry's mouth as his orgasm began. Terry sucked and stroked harder. The first spurt of cum was not big, but the second and third were huge. Terry was surprised at the force of Dave's cum jetting into his mouth but he had been waiting for it, wanted it and he greedily sucked in the hot, salty seed. Dave's cock spasmed six or seven more times, the last few without cum. This gave Terry time to swallow the enormous amount of cum his friend had pumped into his mouth. As Dave's cock slowly softened in his mouth, Terry lovingly sucked it clean. The odd thought that his first blowjob had been from the giving end crossed his mind but he dismissed it. He had loved it and he knew Dave did too. Terry stood, pressed Dave's knees together and then sat facing him on his lap, straddling his thighs. Rubbing his panty and hose covered ass gently over Dave's soft cock he said. "So did you like it? I never did that for a boyfriend before." "It was wonderful." Replied Dave, lightly stroking Terry's tits through the cups of his bra. "I can't wait to tell my friend Cindy about it tomorrow." Cooed Terry. "She's coming over to borrow some of my clothes for a date. You don't mind if I tell her do you? I mean I think she wants to give her boyfriend a blowjob and would like to know what to expect." At the mention of Cindy, Terry could feel Dave's cock twitch beneath his ass. Moving back a little Terry took Dave's hardening cock in his hand. "I guess it would be okay to tell Cindy,' Replied Dave. "Good, I promised her she could borrow my sexiest panties and stockings. She is going to look so hot that I think her boyfriend might even want to take her cherry!" Exclaimed Terry. That comment made Dave's now hard cock jump in Terry's hand. Using his free hand, Terry reached up and pulled the cup of his bra away exposing his hard nipple. Leaning forward he offered it to Dave who kissed then licked and sucked at it. Dave's hands began to caress Terry's ass through the nylon. Moving one hand to the front, he was pleased to find a hard cock pressing against the pantyhose. Terry shuddered at his touch and pressed his crotch down to meet Dave's hand. The phone rang before things could go any further. Terry jumped up startled. The caller id had Dave's number displayed and Terry correctly guessed that it was Dave's Mom. Looking at the time displayed on the VCR, Terry realized that it was after one am. 'Hello." He said, answering the phone. "Oh hi Mrs. Ryan, actually Dave left about five minutes ago. He should be home shortly. Okay, bye." While Terry was on the phone, Dave had been busy getting his pants up and buttoned. They walked together to the door, Terry in only a bra, panties, hose and heels, Dave fully dressed. "I'll call you as soon as I get out of work tomorrow." Dave said. "All you boys say that." Giggled Terry as he leaned over and kissed Dave on the lips. Darting his tongue into Terry's mouth, Dave tasted what could only be the traces of his own cum. Forcing himself to break the kiss he opened the door and with a last look at his friend, now girlfriend he headed for home. Terry closed the door behind him, still hard in his panties and began planning for Cindy's transformation. Once again in his sister's bedroom, Terry peeled the cum soaked panties and pantyhose off, placing them in the hamper. Removing the bra, he folded it neatly and returned it to the top drawer then opened the drawer with the nightgowns. He selected a long, black sheath gown and decided not to wear panties. As he brushed out his hair before the bathroom mirror, Terry noticed that his cock pushed the gown out in a decidedly ungirlish manner. Smiling he turned off the light and slipped into his sister's bed. *** Dave called as promised late the next afternoon. "Hey, my Mom said that instead of walking home so late at night, I could just stay over." "That's great. I am sure Cindy's boyfriend will be pleased to hear that." Teased Terry. "And since I don't work again until Tuesday I convinced her to let me stay over Sunday too. The only thing is she is gonna drop me off and stick her head in the door to make sure that you are okay, what with your parents gone and all." Answered Dave. "So you don't want me answering the door in a nightie? Is that what you are saying?" "Well Duh." Said Dave. "How about a nice skirt and blouse then?" "Cut it out. You know what I mean." Responded Dave. "We'll be there in about twenty minutes. Okay?" "That will be fine. Are you going to shower there or here?" Asked Terry. "I told my Mom we would probably be swimming so I guess I will shower there." Answered Dave. "See you in bit then." Said Terry. Although Terry was wearing white satin panties, he had on regular boy jeans and a polo top, no bra. But what was he going to do about his nails? Dave's Mom was going to notice bright red polish! There was no time to take it off and Terry began to panic. With only five minutes left until Dave and his mother arrived, Terry finally had an inspiration. Rushing to the garage he got a pair of yard gloves, slipped them on and then went out to the front and pretended to be weeding. When Dave and his Mom pulled into the driveway, Terry stood and waved. Going over to passenger side he said, "Hi Mrs. Ryan. Thanks for letting Dave spend the night." "Hi Terry. Well it works out for us too. Tom and I are going to go out of town until Monday. This way he is not alone. How are you doing? Do you need anything?" "No, My folks left plenty of food, money, phone numbers and yard work to keep me busy. I'm fine." Answered Terry. "Okay then. You boys have fun but stay out of trouble. Dave you have the number where we are staying?" Asked Mrs. Ryan. "Yes Mom, we'll be fine." Dave answered with a pretend exasperated sigh. "I am going to pick your father up at work and leave from there, but we will be at the hotel by eight o'clock. Leave a message at the desk if you need us before then and we will call you here." "Yes Mom." Repeated Dave. "No parties and don't invite any girls over." Mrs. Ryan said with a wink. "Bye Mom." Said Dave as he shut the door. As they watched Mrs. Ryan drive away Terry said, "Did she say no panties?" Dave punched is friend lightly in the arm, headed for the house and said, "Come on, I have to clean up. Is it okay to use the pool without a shower?" "Sure, did you bring a suit?" Asked Terry. "Nah, just shorts. Who owns a bathing suit anymore?" "Cindy does." Replied Terry turning to hold the front door open. Dave was blushing as he walked past Terry and into the house. "Um, where do you want me to put my stuff?' Asked Dave indicating the gym bag he was carrying. "Throw it in my room. Let me get rid of these gloves and then I will bring you a suit to wear. Why don't you strip down and wait in my room?" Said Terry as he headed for the garage. Dave entered Terry's room, placed the bag by the closet and nervously removed his shirt. Terry was going to bring him a swimsuit. A girl's swimsuit. Kicking off his shoes he went from being a little nervous to a little frightened. After the suit then what? Panties, bras, dresses? And he had promised Terry that Cindy would do anything her boyfriend wanted. Including a blowjob. Stripping off his jeans he realized that even if he was a little scared, he was also excited. His cock was rigid in his jockey shorts. Deciding to leave the jockeys on, he waited for Terry. Meanwhile Terry had thrown the gloves in the garage and hurried to his sister's room. Quickly stripping, he donned a bright yellow thong bikini that covered but did not hide his erection. The matching top was little more than triangles over his nipples. Gathering up the red one piece that he had chosen for Dave and two towels, he went to his own room. "Well Cindy, what do you think of my suit?" Asked Terry, turning to give Dave the full view. Although Dave had seen Terry's ass the night before in pantyhose, this time it was naked. The thin ribbon of thong ran up between the crack of his cheeks, the yellow seeming to accent the bareness of his skin. As Terry turned back around, Dave was treated to the sight of the outline of his hard cock straining the thong. "Wow." Was all he could say. "That is the ugliest pair of panties I have ever seen!" Exclaimed Terry. "Take them off and I will help you put this on." He said showing Dave the red suit. The sight of the suit made Dave's cock twitch in his shorts. Something that did not go unnoticed by Terry. Slowly Dave pulled his shorts down past his knees and allowed them to fall. Suddenly naked, Dave felt shy. Stepping out of the puddle his shorts made on the floor brought him closer to Terry who knelt down before him and held the legs of the suit open for him to step into. "Ready Cindy?" Asked Terry. Placing a hand on Terry's shoulder, Dave lifted one foot into the suit and then the other. Terry pulled the suit slowly up his legs. "You will need to shave your legs for your date tonight Cindy. Don't worry I will help you." Commented Terry. As Terry drew the suit past Dave's thighs, he could not help himself and briefly placed his mouth over Dave's dick. Giving him a quick little suck and then stopping, Terry stood up, drawing the stretchy red material past Dave's cock and over his ass. Going around behind Dave he slid his fingers into the elastic of the leg bands and adjusted them around Dave's bottom. Dave was breathing hard but not speaking. "You have a really nice ass Cindy." Said Terry as he pressed forward making contact with his hard cock. "Your boyfriend is very lucky." Reaching around to the front Terry pulled the bodice, which was a see through red net, up Dave's stomach and chest and slipped the strap over his head. The cups settled nicely on Dave's breasts, the built in pads pushing his small chest into the center. In a pretense of aligning the cups, Terry squeezed Dave's nipples and felt their hardness. "Nice tits too." "Turn around and let me see." Whispered Terry. Robotically Dave turned. Terry reached out and adjusted Dave's hard cock so that it ran straight up his belly, the head just peeking out off the solid bottom and visible through the red mesh. "You look so hot." Said Terry. "Do you like it?" "Yes, it is so tight and yet stretchy at the same time. I can not believe how excited I am." Answered Dave. "If you are excited now, wait until you see the things I picked out for your date tonight." Said Terry as he caressed and then lightly squeezed Dave's ass through the thin material. "Come on lets go swim. It will cool us off." The girls swam for about an hour; the water was cold enough to make their nipples hard and their cocks soft. Terry checked the time and told Cindy it was time to get ready for her date. This announcement made Dave's cock harden again. As they were entering the house and toweling off, the phone rang. It was a telemarketer, but what Terry said after he hung up was, "That was you're no good boyfriend, canceling your date. But don't worry, I am still going to dress you up and we can have some girl on girl fun. We don't need him!" Taking Dave by the hand he led him into his sister's bathroom. "Come on now, into the shower and let's get rid of that leg hair." Said Terry as he undid the hook on the top strap of Dave's suit. When the water was hot enough, Dave, naked, stepped into the shower. Terry removed his top but left the little thong on. He did not want Dave to see his cock yet. While Dave washed out his hair, Terry gently shaved his legs, controlling the urge to suck on Dave's hard cock. Stepping out of the shower Terry wrapped himself in a towel and then removed his thong. Dave mimicked Terry's movements and placed his own towel above his breasts. Terry then showed him how to wrap another towel around his head and said, "From this point forward you are Cindy." "Yes." Said Dave. "Make me Cindy, your lesbian girlfriend." Terry led Cindy to the bedroom and sat her on the bed. Pulling a chair over, he sat and took one of Cindy's feet in his lap. Taking the bottle of pink nail polish he carefully painted all of her toes, glancing up at her long legs and tented towel. When Terry took Cindy's hand to begin the fingernails, Cindy blushed and asked. "So did you do it?" "Do what?" Replied Terry. "You know, give your boyfriend a blowjob." Giggled Cindy. While she finished Cindy's nails and moved on to her light make up, Terry recounted all the details of the previous night's action. Describing how big her boyfriend was, what it had felt like to have him in her mouth and the taste of his hot cum. By the time she was done, both girls had huge erections under their towels. Getting the hair dryer from the bathroom, Terry dried and combed out Cindy's hair. With Terry standing beside her, it was Cindy's turn to want to reach under the towel and suck cock. Finally it was time to get dressed. Instructing Cindy to remove her towel, Terry went to the dresser and removed the matching black and pink garter belts. Still in his towel, Terry dropped the black one on the bed, held out the pink one and said, "This will go beautifully with your nails." Going behind Cindy, Terry wrapped the belt around her waist and hooked the three little clasps. Getting the black belt from the bed Terry asked, "Would you help me with mine?" Cindy took the garter belt with trembling hands and went behind Terry. Cindy held one end of the belt and reaching around grasped the other end. Having never done this she had some trouble with the little hooks. Finally, Cindy knelt down to see better. After hooking the garter belt, Cindy placed both of her hands on Terry's hips, leaned forward and gently kissed one of his cheeks. When Terry gasped from the unexpected touch, Cindy grew bolder. Cupping Terry's bottom with her fingers, she used her thumbs to pull his cheeks apart, exposing his pinkish asshole. Leaning forward again, Cindy ran her tongue first over the small of his back and then delicately down the crack of his ass until she reached his hole. The pleasure caused Terry to fall forward, bracing his hands on the bed. He spread his legs further, inviting Cindy's tongue deeper into his ass. Terry sighed as the tip of Cindy's tongue circled his asshole and then moaned as it felt the tongue flatten out and slide from his balls, up his crack to the edge of his garter belt. Looking down past his hard cock and through his own spread legs, Terry could see Cindy's rigid member framed by the dangling pink straps of her garter belt. Afraid he would cum, Terry reluctantly straightened up, stepped to the side a bit, turned and said, "Cindy you naughty girl, we have to finish getting dressed!" Leaning back on her heels, Cindy got her first look at Terry's cock. It was just about the same size as her own and very hard, the head a dark red color. Cindy realized that she wanted very much to scoot forward and take it in her mouth. Before she could act, Terry moved away to the dresser and rummaged inside the drawers. Removing two pairs of identical dark brown stockings, Terry handed one pair to Cindy and said, "Here, sit on the bed and I will show you how to put these on without running them." Sitting side by side on the bed, Terry demonstrated to Cindy how to roll the delicate stockings into a ball and then slip them over her painted toes and draw them up her legs. Still sitting, they centered the front straps of their garter belts on their thighs and hooked them to the stockings. "Now stand up, turn around and I will hook the backs and then you can do mine. But no ass licking." Terry teased. They managed, barely, to finish with the stockings without incident and Terry once more returned to the dresser. Removing a pink, heavily padded and under wired bra that must have been from the days before his sister had developed, he handed it to Cindy and said, "Here put this on and I will get you the matching panties. Cindy took the satin covered bra from Terry and slid his arms through the straps. While his friend was getting the panties, she struggled trying to fasten it. Having found the panties and a black teddy for himself, Terry turned to see Cindy unsuccessfully trying to clasp her bra. Handing the full cut pink panties to her; Terry went around and quickly hooked Cindy's bra. Still behind Cindy, Terry stepped into the teddy and shivered as he drew the cool fabric up his shaved legs. Placing his arms through the thin spaghetti straps and moving them into position on his shoulders caused the g- string back to slide tightly between his cheeks. "Stop playing with your panties and put them on." Admonished Terry, "We still have to select you're outfit." Cindy, who had indeed been sliding the silky panties between her fingers blushed and then bent to step into them. Terry reached down and caressed his own cock as he looked at his best friend, her ass framed by pink garters and dark hose, bend at the waist to slide the panties on. I am going to fuck that ass tonight he thought to himself. The high-waisted panties came up to the top of the garter belt, completely covering Cindy's ass and cock, the silky trap rubbing both as she followed Terry to the closet. Earlier in the day Terry had chosen a mid-thigh, white pleated skirt and a thin, pink, V-necked sweater for Cindy. Handing these items to her Terry retrieved the white three- inch heels from the floor of the closet. Holding the heels, Terry watched as Cindy stepped into the skirt, pulled it up, slid the small zipper into place and fastened the single button. Setting the heels on the floor by he bed, Terry said, "After you've put on you're sweater, slip into these heels. Then you can practice in them in a minute while I finish getting dressed. They are a little tricky at first." Terry headed back to his own room, the straps of his garters pulling enticingly at the stockings, his cock throbbing as he reviewed his plan for the rest of the evening. Following Terry's instructions, Cindy pulled the tight sweater over her head and tugged it into place. The V-neck dipped to just above her bra and gave the illusion of firm teenage breasts. Sitting on the bed, she easily slid her stockinged feet into the high heels. Cautiously she stood up and taking very small steps, headed for the bathroom to see what she looked like as Cindy. She was still staring at herself when Terry retuned wearing boy's jeans, a black football shirt that hid his teddy and regular sneakers. "Wow Cindy, you look great!" Terry exclaimed from the bathroom door. So enchanted with her image, Cindy did not notice the boys clothing on Terry. "I feel so different. I look like a girl. Well not a great looking girl, but feminine, you know, sexy. And you were right the heels are a little tricky to walk in." Answered Cindy. "Don't worry, where we are going you won't have to walk at all." Terry responded. "Where we're going, what do you mean?" asked Cindy, turning and seeing for the first time the way Terry was dressed. Seeing the alarmed look on Cindy's face, Terry said, "It's okay. We are going to go to the old drive-in theater in Brighton. It is two towns away and no one will see us, we will be in the car." "But how will we get in, the cashier will know! Look at your nails for heaven sake." Trust me Cindy." Terry said, moving up next to her. "I will wear my Dad's driving gloves and we will bring some soda with us. While you get used to walking around in those adorable shoes, I will make some popcorn. We won't have to get out of the car. Besides, doesn't the thought of making out with her boyfriend in a dark drive-in excite Cindy just a little bit?" Cindy looked in the mirror and saw a plain girl standing next to a plain boy. She did like the thought of making out with her boyfriend and the fact that her boyfriend was wearing girl's lingerie under his baggy clothes made her cock twitch against the pleats of her skirt. Well, these shoes are adorable." Cindy said with a smile, "and if you promise we won't get out of the car..." she trailed off. "I promise." Said Terry. "Now walk out into the kitchen with me, but stay in front of me, I want to watch that sexy ass of yours." Ten minutes later, a large bag of popcorn and a cooler full of soda in hand; Terry's painted nails hidden in the thin driving gloves, they backed the car out of the driveway and headed for the movie. The trip to the theatre was uneventful and the cashier at the gate would probably not have cared if they were naked. Terry parked the car a safe distance from other vehicles, but not so far away as to attract attention or trouble. Even though no one was aware that they were a rather odd couple, they both felt better when the sky was dark and the movie had begun. It was a movie they had both seen before and after a few minutes Terry placed his arm on the back of the seat bench and said, "Cindy, why don't you slide over here and give your boyfriend a kiss." Cindy moved over, her skirt riding up enough to show the tops of her stockings. Snuggling up to Terry, she kissed him, running the tip of her tongue around his lips, much as she had earlier run it around the tight bud of his asshole. Terry moved his arm from the seat and placed it over Cindy's shoulder, pulling her closer to him. He plunged his tongue in and out of Cindy's mouth, slipping it repeatedly between her lipstick slick lips. As Terry's left hand found the soft mound of her breast, Cindy broke the kiss. Breathing hard Cindy said, "You were right, it is exciting to neck with my boyfriend at the drive-in. I almost came when you touched my breast." "You have beautiful breasts." Said Terry as he continued to knead them through her sweater. "You don't think they are too small?" Laughed Cindy. "Well, it is kind of hard to tell with that sweater on, perhaps if you took it off?" Teased Terry. "Oh no, not in public!" Exclaimed Cindy. "But perhaps if you put your hand under it you could get a better feel for the size of my breasts. Pun intended." Terry moved his hand down and ran his fingers lightly over the inch of bare skin that separated Cindy's sweater and skirt. Encouraged by Cindy's sighs, he leaned forward and as his hand crept under the edge of her sweater he began kissing her again. As Terry's hand edged closer to her bra, Cindy tentatively put her hand on the bulge in Terry's pants and was rewarded by a moan. As she squeezed his cock and cupped his balls, Terry's finger slid under her bra and touched her nipple. Cindy felt like an electric shock traveled from her nipple to her hard cock. It was all she could do to not cum. "Terry?" She whispered. "Yes?" "Undo your pants, I want to feel it. I want to suck it. Please?" Surprised at her boldness, Terry removed his hand from her sweater and quickly undid his pants, pulling them down just a bit. In the flickering light of the movie, Cindy could see his hard cock pressing against the silk teddy. Scooting her ass back so she could bring her face closer, she was unaware that her skirt had ridden well above her stockings and that her pink pantied ass was in view. Putting two fingers under the lace leg opening, Cindy pulled it away to reveal Terry's erect cock, dripping pre- cum. Unable to resist, she cupped his soft balls in her hand and for the first time thrilled to the feeling of a hard cock sliding into her mouth. As the soft head passed her lips, Cindy creamed into her panties. The moment Terry's cock passed between Cindy's lips and touched her tongue, Terry came also. He couldn't help it. The excitement of swimming and dressing together, the sight of his best friend, stretched across the front seat of the car, her skirt up exposing her pink panties and stockings and her mouth surrounding his dick was too much. His spasms were strong, but fortunately for Cindy, Terry did not cum very much. He had been drained several times the day before and had jerked off twice that morning. Cindy easily and greedily swallowed the small amount of hot cum that came out of his dick. It was quiet in the car while they caught their breath. Finally and with reluctance, Cindy pulled her mouth from Terry's cock and pulled the teddy back over it. Sitting up and tugging her skirt back down, she said, "I messed my panties." Smiling, Terry replied, "I know the feeling. Do you want to stay and watch the movie or go home and change?" "Let's go home, we've already seen this and there has got to be something more interesting to do than stay." Said Cindy, raising one eyebrow. Terry started the car and glancing at the clock, was surprised to see that they had only been there for about forty-five minutes. It was just eight o'clock. They had a long night of fun ahead of them. After pulling the car into the garage and closing the overhead door, Terry asked Cindy to put the remaining sodas away while he went to his room to remove his boy clothes. Kicking off his sneakers, Terry stripped down to just his garter belt and stockings. Carrying the teddy, he found Cindy in his sister's bedroom. Cindy was just reaching up under her skirt to pull off her panties when Terry entered, "Here, let me." Said Terry, kneeling in front of her and sliding his hands up her legs to the waistband of the panties. As he pulled the soiled panties down her legs, Terry put his head under the short skirt and took Cindy's soft cock into his mouth. Gently sucking and rolling Cindy's meat in his mouth, Terry stopped as he felt the cock harden. Teasingly pulling his mouth away, Terry said, "Let's get you something fresh to wear." Handing Cindy a pink nightie that would barely cover her ass, Terry said, "Go in the bathroom and put this on. Leave your bra on though." "Um, are there panties to go with this?" Cindy questioned as she took the garment. "Yes, but I want to see your cock hard, like it is getting now." Giggled Terry. Blushing, Cindy went into the bathroom. Terry pulled the black bustier that he had spotted under the garter belts out of the drawer and thankful that it zipped up the front, put it on. Removing his garter belt, Terry clipped the straps of the bustier to the tops of his stockings, finishing just as Cindy emerged from the bathroom. "Gather up all our dirty things and throw them in the hamper by the closet, then meet me in the bathroom." Said Terry. While Cindy cleaned up, Terry went to the medicine chest in the bathroom and took out a small jar of Vaseline. When Cindy came in a moment later, Terry said, "Stand in front of the mirror and spread your legs open a bit for me," Puzzled but willing to do anything, Cindy did as instructed. Lowering himself to his knees, Terry said, "That's it. Bend over a little more. Open your legs wider, yes, very nice. Now watch yourself in the mirror as I get you ready." Before Cindy's glance could reach the mirror, she knew what Terry meant by "getting her ready." She watched the muscles of her stomach tighten as Terry's finger, loaded with the cool, slick Vaseline touched her asshole. Before her asshole could tighten, Terry had slipped his finger into her up to the first knuckle and then just as quickly, backed it out. Terry plunged just the first inch of his finger in and out of Cindy's ass smearing the lubricant around. He marveled at the hot tightness of her hole and as Cindy's moans increased, he paused and then very slowly pressed his finger until all of it was buried inside her. Then he stopped. Cindy, knuckles white as they gripped the counter, could not believe how strange yet wonderful Terry's finger felt as it probed her ass. When he paused, she felt empty and was ready to push her ass backward when she felt him touch her again. When the intruding finger did not stop but continued slowly working it's way further and further up inside, Cindy whimpered with pleasure. Looking through barely open eyes at herself in the mirror, Cindy shivered. Her lipstick was slightly smeared and getting worse from her tongue running wet over her lips. The satin bra made small mounds under the nightie and her cock, now fully erect was just visible through the sheer pink material. The moan as Terry withdrew his finger just as slowly as he had put it in was one of lust and desire. Terry's left hand involuntarily reached for his own straining cock when he heard Cindy's moan. Reluctantly he let it go, stood and said, "Let's go into the living room." When they reached the living room, Terry instructed Cindy to kneel on the coffee table. With urgent need, he coated his hard cock with Vaseline and moved behind her. Placing the slippery head against the pink, waiting hole of his friend, Terry asked, "Do you want this? Do you want my hard cock in your ass?" "Yes, put it in me, please Terry." Terry moved forward and slid his hard, very greasy pole slowly into Cindy's ass. With his balls firmly pressed against Cindy's asscheeks, he finally stopped. Her tight passage squeezed and released him as it tried to force the hard cock out. Finally Cindy's ass relaxed and accepted the hardness that filled it. Terry looked down and almost came. The bustier was tight across his chest, the garters taut to his stockings. Cindy's own hose covered legs were trapped between his, her pink garters two straight lines down her ass. The pink band and straps of her bra clearly visible beneath the nightie she wore. Moving slowly he began to fuck Cindy's ass. Pulling most of the way out and then pushing forward he was rewarded after only a few strokes, when Cindy began to wantonly push her ass back to receive his cock. Leaning over her and supporting himself on one hand, Terry used his other to rub and pinch at Cindy's breasts through her bra. As Cindy's moans of "Yes, fuck my ass" became louder and faster, so did Terry's pace, plunging in and out her hole. When he could feel the cum building and ready to jet from his balls, he urged her into an upright kneeling position. With Cindy's back pressing firmly into his lace covered chest, Terry moved his hand from stroking her titties lower, grasping at her hard cock. He stopped moving his hips and let Cindy slide up and down on his cock. Pumping her hard cock in time with her thrusts, Terry knew they would both come soon. Cindy, impaling herself as far onto Terry's cock as she could loudly moaned, "Oh Terry fuck my ass, fuck my cock with your hand. I am going to cum, you are making me cum. Ohhh... yes." As Cindy's cock spurted her hot cum into the air and onto the table, Terry came deep in her ass. The feeling of cum hitting the walls of her ass made Cindy groan and she reached down and putting her hand over Terry's, helped him pump the last of her own orgasm out. They were both still gasping and moaning with pleasure when Mrs. Ryan stepped around the corner of the room and said, "Well girls, what have we here?"