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~*Teaching the Sissy Neighbor Boy*~Marion eyes opened in dismay at the sight of her neighbor's son, Jeff. She wasn't sure if he had just turned 18 or 19, but that didn't matter just now. The dark-haired young man she had barely noticed in anything other than a passing way, was hunched over in front of his sister's dresser. Dressed only in a black bra and black panties pulled down to the knees, he was ravaging his young fist. He was in the final strokes of jerking off in front of the mirror. His right fist was a blur. The sunlight had penetrated the girl's bedroom window at just the right angle to flood the room with light, almost like a theatrical spotlight. It made the boy's pale skin even paler with a rosy glow. From her position in the window of her bedroom, she could see every detail of the lad's slitted eyes and slightly gaping mouth. His face was feminine with matchless complexion. His lips were full and pouted outward. His long dark hair, in this new context, completed the picture. Marion determined that his member was rather small, but rigid as only the pricks of young men can be. She wished she could see it better. She could almost feel his juvenile groans of pleasure as his slim hips thrust forward. He shot his load into a waiting tissue cupped in his left hand. Jeff was trembling with pleasure and gazed long and passionately into the mirror. He turned and posed with his round little ass facing the mirror. He looked over his shoulder at himself and made a few thrusts backwards as though taking a stiff cock up his ass. Then he stood up and carefully cleaned his prick before stepping out of the panties. He held them to this face and rubbed them all over. Next he fondled his balls with the crotch of his sister's panties held against his nose. Suddenly he jerked his head and stripped off the clothes, stuffed the underwear back into the drawer and scrambled into his clothes, dashing out even before he was fully dressed. Marion turned and saw Jeff's sister's boyfriend's car drive up the driveway. Denise, a beautiful dark-haired young woman of 21, leaned over and kissed her boyfriend with a lingering kiss. He took the opportunity to fondle a breast under her sweater. She didn't pull away as his hand seemed to move everywhere under her clothes. Then, with another quick kiss, she jumped back and skipped into the house. Marion watched the boy put his hand onto his cock and give it a squeeze before he backed out of the driveway. She knew that he would be off home to beat his meat. She tried to visual Ted laying on his bed pounding away on his boner. She moved back to her bed, lay down and slowly stroked her clit thinking about the events she had just witnessed. She was already saturated with vaginal fluid. It didn't take long for her to reach climax, rear her hips upward and grunt heavily-knowing she was totally alone. In fact, by Wednesday, Marion usually was in some real need of release. Her husband commuted to his job 250 miles away. Marion had said she didn't want to move to Detroit, and if her husband wanted to go, it would be without her. They compromised. So now Jim flew out every Sunday afternoon and returned Friday's. That meant that Friday night was a heavy sex night for them. Saturday was okay and Sunday morning was a leisurely fuck and suck. A few times Marion had knelt in front of him as he was ready to leave and sucked his cock so he could relax better on the flight. Recently, she had stopped this because he seemed to be already in the air as he waited for the limo to take him to the airport. This part time relationship had actually worked in favour of their relationship. Marion, conscious that her husband could easily find someone else, had exercised rigorously to maintain her slim and powerful body appearance. It also kept her large boobs from increasing beyond their current D cup size. She treated herself to regular manicure and pedicure sessions. So by the time Jim came home on Friday, he was treated to a very attractive package. The fact that she kept her pussy bare was a particularly sexy touch. So, by Wednesday she was getting horny. She usually gave herself a vigorous session of masturbation that began in bed before she got up, and was continued in the afternoon. It was just as she was about to start that she had seen young Jeff's performance. She had been completely naked as she witnessed his dramatic efforts. After the first come, she still had the image of the young boy in her head. She couldn't wait to see if he would repeat this tomorrow. Jeff did not disappoint her. Marion saw him hurry up the walk and disappear through the side door shortly after 3:30 PM. She was positioned a few feet away from her darkened bedroom window. She had set up her husband's expensive digital camera with the zoom lens attached. She had set the distance for focus and made sure the iris was set for wide open. The Field of view was inside the bedroom only. Like a precision clock Jeff entered and went straight to the underwear drawer and carefully dug out one of Denise's black bra's-possibly even the one Ted had felt yesterday afternoon. In his other hand he took up a pair of black panties. He held the panties to his face and inhaled sharply. He then swiftly stripped naked. His cock was already stiff. It stood pointing straight up. Marion clicked the camera and observed the shot in the small display screen. It was sharp with plenty of light from the convenient sunlight. Jeff gave his cock several quick and firm strokes. His cock bobbed as he released it. Then he put his socks into the bra cups and awkwardly put on the bra. He mugged into the mirror. Click. Marion got another dandy shot. Jeff slowly drew the panties up, stroking himself through the fabric, before pulling them snuggly up to cup his little balls. Since the panties were a low cut style even his tiny prick forced the head above the waistline. He then posed in front of the mirror. Click. He faced away and admired the way his slim ass looked. He was small enough that these tiny briefs gave better coverage than they would have for Denise who had a more womanly shape. Jeff was acting like a coy young girl to the image in the mirror. He teased the panties down. Then, to Marion's surprise, Jeff gave his little prick several stinging slaps. This made his cock dance and vibrate like a tuning fork. He then turned and gave his bare ass a firm slap, then he gave the other cheek a good hard one. He kept this up for about 15 or so slaps. Marion took about 8 more shots during this time. Finally he got to the main event. He posed with his ass facing the mirror and he pounded away like a fiend. Finally shooting his goo into the tissue. He then smiled at the mirror like a satisfied cat. But he had one ear listening for the arrival of his sister. He stood with his hands over his head, cock still hard almost like a slave girl waiting for the lash. Marion got this pose as well and knew that the young man was now going to be in her power. Just then, Denise arrived. Jeff hurriedly replaced everything and slipped out of the room. Marion was going to settle back on her bed for another session of masturbation when she saw Denise come into the room. She walked over to her dresser and opened the underwear drawer. She removed the same underwear that Jeff had used moments before and sniffed them. She smiled. Marion was surprised. Most sisters, if they thought their brothers were going through their things would go ballistic. Denise went over to her door and locked it. Then she came back and quickly stripped. She, too posed nude in front of the mirror. She fondled her tits with both hands, then went and lay on the bed. She teased herself for a few moments, but then got down to some serious whacking off. She writhed all over the bed letting her right hand pillage her crotch as though she was being forced open. Her other hand roughly groped her lovely tits. Marion quickly took several shots of Denise. Why not, she thought? That girl is one hot piece. In fact, Marion was so steamed up, she knew she would come if she so much as touched her swollen clit. As it was, she could feel the juice running down her thighs as far as her knees. Denise flipped over onto her back and thrust her gorgeous ass backwards as she continued to thrash her clit. Finally she thrust back and then jammed her hips into the bed as she came. She rested on the bed for a moment. Then she got up and put on a robe. Marion figured she was going for a shower. She wished she could join the girl. Although she was not a lesbian in the strictest sense of the word, she had had a number of girl friends at school who had found excuses to visit her and most had wanted to fondle her big tits. She had pretended reluctance, but secretly it was nice to have someone worshipping your body. She extracted a requirement that the girl of the day strip naked and play with her cunt until she came. The girls all seemed more than willing to jerk off this beautiful teenager. She also found it exciting to have the girls play with themselves as she watched in fascination. Once she left high school and went to college, the lesbian acts diminished and she started screwing guys. Marion called Jeff's mother around 7:00 PM and asked if she would let Jeff come over to help her with some computer glitch. She said that Jeff would be happy to help. At 7:15 PM Jeff arrived. He seemed a little vexed at having to come over. "My mom says you have a computer problem." "Yes. I remember her saying that you were an ace at this stuff." "Not really, but I guess I could look at your problem." "Come with me. It's downstairs." She led Jeff into the finished basement and then into a large office space with no windows. "I have a file or two that I'd like you to look at." The screen saver was active. Jeff hit the space bar and a Windows Explorer file list came up. "Click on that one, Jeff." She point to a JPEG file JO001.JPG. Jeff looked at her and double clicked. To his shock, a full screen image of him, cock in hand, panties pulled down and bra strapped to his chest popped up. His jaw dropped. He swallowed hard, then looked at Marion. "How did you get that?" "Boys who beat their meat in front of an open window deserve what they get. I think your parents are going to be very, very upset when they see these pictures. And I think Denise will be furious." "Huh? You're not going to show them to my mum and dad, are you?" "That's up to you, Jeff. If you're a good boy and do what I tell you to do, no one will find out." "What do you mean?" "Well, Jeff. I found it very exciting to see a young man like you playing at being a girl and jerking off. I'd like to watch you do it some more. Right here." "I can't. I have to go home." He started to leave. "If you walk out that door before I tell you to, your parents will have these pictures 5 minutes later." He stopped. "Why are you being so mean to me? I never did anything to you." He was about to cry. "Don't waste your tears, young man. Strip naked. Now!" Jeff gave her baleful look. There was no mercy in her eyes, just a hungry lust. He slowly started to undress. "Do you need help?" He shook his head and removed his shirt. He wore no undershirt beneath. Marion admired the smooth hairless chest. He dropped his jeans and stopped. "What are you waiting for?" He hesitated for a moment, then slipped his white Jockey shorts off revealing a slender penis that was at rest. "You look stupid with just your socks on. Take them off, too." Jeff did. Marion stepped around him to admire his pale little ass. As she took it in, she knew that this boy had to get fucked. She was going to buy a dildo to wear and she was going to plug him until he screamed. "Now play with your dick. Get it hard." Jeff was miserable. He took his prick and tried to get it aroused, but it wouldn't move. "Maybe you need some help. Bend right over." She folded him in half when he didn't move and gave him a stinging slap on the buttocks. She then delivered another dozen. To Jeff's surprise and chagrin, his cock was stiffening at an alarming rate. As Marion slapped him harder he was afraid he was going to shoot off. "Start stroking, Jeff, or this little ass of your is going to catch fire." Awkwardly, Jeff took his cock in hand and began the obscene act. Hunched forward he began to pick up speed until he shot his load. He automatically caught it in his hand and then was confused since he did not have his handy tissue. "Taste it, Jeff. It's your mess. In fact, I want you to eat it. Now!" Reluctantly, he licked the come from his hand and gamely swallowed it. "Done like a real lady. Don't move, yet. I want you to do it again in a minute." "I can't." "Oh, you will, Jeff, and you'll do it again after that. You are going to be a sperm machine by the time I get through with you." Marion opened her dress revealing her nude body. Jeff's eyes gaped open at the sight of the woman's body naked before him. "I want my cunt sucked, Jeff. Kneel in front of me and lick it. I'll teach you what to do." Jeff obediently fell to his knees and let Marion guide him. His tongue licked eagerly over her bare cunt, finally lingering on her swollen clit. He let Marion instruct him on taking the clit entirely into his mouth and letting his tongue lick circles around it. He was a quick study and soon had the mature woman groaning through the most powerful orgasm she had ever experienced. She slumped over the boy forcing him onto his back. Her wet cunt pressed like a suction cup over his mouth and Jeff was gagging, but his cock had snapped to attention. He was muling and kicking his legs in fear as his breathing labored. Marion eased up enough to let him take a breath before slumping back and riding his face for a dozen or so strokes. Then she turned to press her big ass right over his nose. Jeff gasped as the large buttocks pressed over his nose. His cock was throbbing. Marion gave the diminutive prick a firm slap and watched it vibrate. She repeated this over and over again lifting herself up slightly from time to time to keep Jeff alive, but dropping quickly to keep him pinned. After 30 slaps the kid shot his load without touching himself. It was a meager puddle and it cooled quickly on his slim stomach. Marion got up and smiled at the boy who was nearly in tears. "Let's go. I want to clean up." She took his hand and yanked him up. Marion had to pull him along into the bathroom. "Get into the tub. Now!" She slapped his face hard. He obeyed with a sob. "Lie down on your back." She stepped into the tub and straddled him. "Open wide." She started to piss, aiming her stream at this mouth. He tried to move his face, but she dropped to her knees over him and held him in place until she had squeezed the last drop out of her urethra. Jeff was now crying with great sobs. "Shut up, Jeff, I want my cunt cleaned up." She shoved herself onto her his face and made the kid eat her to another orgasm. Once she had sated herself, she ordered Jeff to have a shower and clean himself up. As she watched him, she planned tomorrow's shopping trip. She imagined his tiny ass in the air, her new huge dildo driving up his shit spot. It was a fantasy that was soon going to come true. Chapter 2 "Perhaps I should call you, Jessica, rather than Jeff." The boy was not amused as he stood in front of Marion's full length mirror. He had had two days to try to figure out how to get out of his predicament. His presence in her room indicated his complete failure. He had not attended his sister's room yesterday. She had been waiting for him to get in from school this afternoon and had flagged him over to her house. She knew that his parents would not be home for hours. And his sister would not miss him. She had ordered him up to her room where he stripped in front of her. Rather than immediately abuse him, she had forced him to dress up in some lovely and very sexy lingerie. He had stiffened in the new panties. Marion took him into her bathroom and gave his face a complete makeup job, finishing with a long brown wig. The effects were unbelievable. Jeff stayed rock hard during the entire procedure. Once the wig dropped over his head, he was looking at a stunning young girl in the mirror. "You look like a little slut, Jessica. One who needs her bare ass whipped raw." Jeff turned to look at Marion. "Did you think that dressing up would change my plans? Jessica, I'm going to take your panties down and use a leather strap to teach you to keep your hands out of other peoples drawers. Then we'll do something else." Jeff was wobbly on the 5" heels. He tottered out into the bedroom as Marion observed his awkward movements. "Jessica. Please get the leather strap out of the drawer by the bed and bring it here." The boy slowly obeyed and once he had the strap in his hand, he couldn't resist stroking it. He knew that his naked ass would be the next thing to feel it's touch. Marion wore a leather skirt and a leather jerkin of a very shiny black leather. Jeff could smell the leather. Her huge breasts were pushed way up and swelled over the restraining cups. She wore black high heel boots. "Kneel in front of me, Jessica. Now hand me the strap. Tell what is going to happen now?" "I don't know." Her hand lashed his face. "I just told you, you stupid slut. I want to hear you say it." Jeff put his hand to his face. A tear formed and started to slide down his cheek. "I'm.. . I'm going to take my panties down so you can strap me on my bare ass." "Exactly. Well? What are you waiting for?" Jeff stood up and started to lower the panties. "Leave them at your knees for now. Bend right over. Just like that. Don't move an inch while I whip you." Marion carefully pulled back the strap and let the first stinging slap catch Jeff on the fullest part of his slim cheeks. He jerked and cried out. She followed with two more to punctuate her distaste at the noise he had made. "Not a sound, you little bitch." She then went to work with a will. She moved around and held him from time to time as she measured each blow. Crack!! Crack!! Slap!! The noise filled the room. Jeff was whimpering softly, but to his horror his tiny cock stayed rigid. In fact, he couldn't believe the fire that was building in his balls. He was afraid he would shoot his load without touching himself. The desire to grip his prick was almost overwhelming. He watched himself-looking like a beautiful young girl-getting her bare ass strapped to an angry red. Marion's huge breasts heaved in a way that thrilled the young boy. He couldn't help himself. Finally Marion paused, and though Jeff was relieved, he was disappointed in a way. He had been fascinated by the sight of the young girl getting strapped. He had become a voyeur at his own chastisement. Then Marion pulled off her leather skirt to reveal a large dildo strapped in place with large leather straps. Jeff stared at the plastic prick and suddenly knew what was next. He was too slow to move, however, with his panties at knee level and the heels making him almost helpless. Marion gripped him and forced him to his knees. She held him as she slid the pre-greased pole against his blazing cheeks, then forced them open. She managed to drive the cock head up his little rosebud about three inches. Jeff was in real agony. Marion stroked into him. She was not adept at this initially, but quickly found the rhythm. Jeff's asshole started to ease with the huge dildo coring him out. In fact, as he watched in the mirror he was reaching the point of no return. He grabbed his cock and wrenched it a few times, causing him to become spastic as the fluid shot out of his urethra. He almost screamed with a mixture of agony and ecstasy. Marion continued to hammer his ring as he pulsed in a near frenzy. Jeff finally began sobbing. He realized what he was. A homosexual. A young effeminate suitable for fucking in the ass. For now, it would be Marion's plastic prick that trained him, but soon the real thing would be replacing it. Jeff realized that he really was a Jessica. With that knowledge suffusing his mind, his sphincters eased and he pushed back to take an extra two inches of the massive latex replica. A final dribble of semen was forced out the end of his throbbing prick. Even as he ate Marion's cunt for the third time later that evening, he was dreaming of a big hard prick going up his ass. He would be her sex slave for a while, but Jeff would now be out hunting for the flesh and blood boners that he knew would be eager to ram up his tiny but very cute little asshole. For Marion, she was so keyed up, that she came 4 times before letting Jeff head back home with his very sore ass. As he left, she thought about his sister Denise, and wondered what it would be like to fuck a big girl like her with her new plastic dominator. Chapter 3 Denise was bored with Ted. Sex with him was too routine. He didn't eat pussy, so she refused to suck his cock, even though she wouldn't mind. He had a great body and a big dick, but all he could do was pump like a robot until he shot his load. She wanted more and she wanted strange. She lay on her bed wondering where Jeff was. He was spending a lot of time away in the evenings these days. Did he have a girl friend? She didn't think so. She knew he must be beating off playing with her underwear, so he didn't have a girl. She wondered what it would be like to watch her brother jerking off. It might be neat. But what then? She didn't feel like screwing him. He was her brother. But he was really cute for a kid. More like a girl. She stretched out nude on the bed and began to play with herself the way she usually did after school. Then the phone rang. She was going to forget it, but the caller was persistent. She got up and took the portable from the hall. "Hello?" "I see you're being a naughty girl, Denise." "Who is this?" "Take a look out your bedroom window." Denise walked over to the window mindful to keep away from enough because she was naked. She looked across the way and saw her neighbour standing in her bedroom window. She was naked but shielded in the room so that only Denise could see her. She waved. "What the hell are you doing?" She was going hang up in anger, but a bit of curiosity tempered her anger and she listened. "I thought you might like to come over and join me. Your brother is over here, or should I say, your sister." "What's that supposed to mean." "You'll have to come over to find out. And by the way, you look gorgeous with nothing on. It's a shame you'll have to get dressed to come over. Oh. Some of your underwear is missing because Jeff is wearing it. He'd like to model it for you. He'd be so unhappy if you didn't come over." She hung up. Denise stood looking at Marion whose smile looked a little cruel, now that she took a closer look. She pulled the curtain shut and sat on the bed. She felt like calling Ted, but changed her mind. What was going on? Her neighbour was screwing her brother. He was only 18. She thought she could handle the woman, so she decided to go over and get into it with her. Denise dressed in shorts and a tee-shirt. She pulled on her sandals and walked purposefully over to Marion house. The door opened as she came up the steps. "Hi, Denise. Come in." "What the hell is going on? Where is my brother?" She stood with her hands on her hips ready to challenge the woman. Marion stood naked except for her high leather boots and leather gloves. She made an impact on the girl. Denise stared at her, noting the absence of pubic hair. The woman had a pretty firm body and really big set of tits that did not sag very much in spite of their size. "Calm down, Denise. Jeff is downstairs waiting for us. He's happier than he's ever been in his life." Cautiously, Denise walked down the stairs behind Marion and found herself admiring the firm rear end so excitingly displayed above the boots. In fact, Denise began to feel sexual arousal beginning in her genitals. "Well, Jessica, this is the moment you've been dreading and waiting for." Jeff looked up at his sister with haunted eyes. He was bent over wearing a pair of extremely high heeled pumps, his legs had been cleaned up of the slight bit of hair he once sported. His black panties were lowered to the knee hollows. His penis was rigid. Marion had dressed him in a long wig, and spent some time on his makeup. The black bra was more expertly arranged, making him appear very feminine except for the raging if diminutive prick. Denise was stunned. Her brother looked so much different dressed this way. She was unable to avoid looking at his erection. He was shame faced and looked away from her. "She's a little shy today, but she's going to put on a show for you. I felt that you deserved to see her properly punished for her inappropriate use of you lovely panties and bra." Jeff couldn't look at them. "Jessica, my dear, it's time for your beating. I want you to show your sister what you've been doing in her room. Now!" He looked miserable. "Tell us what you're going to do, Jessica. Denise wants to know what to expect by way of repentance." He began to stammer until Marion delivered a stinging lash across his already reddened buttocks. "Ow! . . . I .. I'm going to beat off while you watch because I always go into your room and wear your panties to get me hard. I'm sorry, sis, but I couldn't help it. I mean, it was so . . I can't explain it. She caught me and made me do this." "That's enough, Jessica, get ready to stroke yourself. I'll beat her until she shoots her load and then you'll give her the second dose of the strap, if you want. She really does like to have her bare ass strapped good and hard. It will bring her little penis right back up to full hardness almost immediately. And don't be shy about laying it on. She can take a lot." Marion then turned and stepped into a solid lash across the fullest part of his cheeks. He yelped and immediately took his cock in his right hand. It quickly became a blur as Denise watched the whipping take place. She was overwhelmed by the sight of her brother masturbating like this. The sound of the strap on his ass, his whimpering, and the woman's heavy grunts as she laid the lash on his ass with authority were really getting her aroused. Jeff was sobbing, but his hand was like a machine as it thrashed up and down. He started to moan and buck his hips, then he gasped and shot the first wad into his waiting hand. Several more jets splashed into his palm as Denise stood goggle eyed at this spectacle. Marion finished him off with three well placed stinging strokes of the strap. "Well. He performed very well this time. Your sister brings out the best in you, Jessica." She eyed the girl closely, looking for signs of arousal. She didn't need to look too hard. Denise was saturated with her own come. She was so close to orgasm that Marion knew she could be seduced. She put her hand on the girl's shoulder. "Let's do something nice for you." She let her hands cup the large breasts. Denise's nipples were jammed against her light top. Marion pulled each nipple and saw the girl's eyes close in passion. She let her right hand drop to the girl's crotch. She felt the steamy warmth and stroked her firmly. Denise was unable to resist as Marion stripped her naked. "Denise, you are lovely. Even more than I imagined. Let's lay down on the couch. I want to eat your pussy. Then you can eat mine." The two women began their mutual love making in earnest as Jeff stood gaping at them. His cock, which had shriveled after the jack off, now slowly firmed up. He watched as Marion spread his sister's legs and expertly licked her cunt. She moved her mouth from side to side in delicious oral ministrations. Denise was no match for the woman who finished her off in a matter of a few moments. Denise was a noisy fuck and she groaned and grunted as she came in spasms wave after wave. As she lay panting on the couch, Marion knelt over her. "Now. Eat me. I want to come." |
 TeleMate | Mommy Jenna |  |
| Status | Available | |
| Phone | 1-888-649-0741 | |
| Sex | Female | |
| Age Range | 36-45 | |
| Ethnicity | Caucasian | |
| Bodytype | Average | |
| Eye Color | Brown | |
| Hair Color | Blonde | |
| Cup Size | A | |
| Persona | Straight | |
| Category | Mature | |
| My Page | http://phonesexstarlets.com/mainjenny.htm | |
| My Friends | See My Friends Listed on PSC | |
| Description | I'm a sexy, naughty Mommy who would love to give you all the love and attention you crave. My nipples are long and get very stiff when being fondled and sucked on...which makes my pussy throb for your stiff cock. M'mmm - call & let Mommy pamper you. | |
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