Window Show Ch. 01

Josh opened his eyes long enough to look her in the eyes imagining she was next to him instead of the house next door. "I'm nine inches long fully erect and six inches around."

T imagined that his young and virile cock in her pussy as she removed her thong. "Josh, tell me what you would like to do to me?"

Josh stuttered a bit as he looked at the sexy naked MILF in the window next door. "I would want you to climb on top of me and ride me so all nine inches is inside of you, while you're on top I would squeeze those beautiful tits and play with your nipples like I've watched all the men do to you.". T shuttered from the rush of hearing how he had seen her be used by other guys, knowing what she liked, knowing when she had an orgasm, knowing when she had swallowed cum.

Josh blurted out, "I'm getting close!" T could also feel her own orgasm building quickly.

T commanded him, "Let's cum together, I want you to squirt on the window so I can see your cum. Wait for my command." Josh slowed his strokes slightly as T increased her play until she suddenly she cried "Now!". Josh quickened his pace and as T started writhing in the chair from her orgasm ropes of cum squirted out of Josh's engorged cock onto the windowpane. T watched as rope after rope painted the window until she could no longer see his cock.

"Damn, that was hot!" Josh exclaimed. T agreed letting him know she had enjoyed it too.

T relaxed with her legs spread wide on the windowsill and her pussy open wide. As they continued to recover Josh asked T about all the men she had sex with and whether or not her husband knew. T let the curious young man know that both enjoyed playing around some and that her husband actually encouraged and enjoyed hearing of her exploits. They continued to discuss her exploits more like old friends enjoying a beer than next door neighbors spying on each other.

Eventually T told Josh that she needed to be going but as long as he kept their arrangement secret she would leave her curtains open so he could see her anytime she was in the bedroom, no matter who she was with. Josh readily agreed and thanked her for her trust. Blowing each other a kiss they hung up for the night, after cleaning up T began to plot how she could go even further with Josh.

The teasing went on for several nights, T would dress sexy and slowly strip for Josh as he stripped for her Sometimes, Josh would take the lead and sometimes T would, either way it would end with both of them naked in front of their respective windows showing everything to each other while having a huge orgasm. Since getting back to Chicago the kids had been wanting to spend the weekend with friends. T finally gave in and let the kids go. Shortly afterwards she texted Josh and gave him a location to meet her Friday night, she was ready to take this one step farther.

As soon as the kids were out of the house on Friday afternoon T began getting ready to "pop Josh's cherry". Looking out the bedroom window she pulled the blinds so Josh could not see her getting ready. She wanted to see his response firsthand and that would happen later tonight.

Getting naked while she adjusted the shower T began to sensually massage her tits and gave her pussy a slow rub. Stepping into the shower T allowed the warm water to cascade down her body, enjoying the feeling as it warmed her all over. Making sure her entire body was clean and smooth T spent extra time cleaning her ass and pussy so Josh's first time would be enjoyable. She laid out a basic plan to how the night would go. After picking Josh up they would return home. Once there she would start things off but hoped Josh would start taking the lead as he grew comfortable. Slowly she dressed taking care that everything was perfect, she hadn't been this nervous since she lost her virginity. This was different though; she was going to initiate Josh into manhood by giving herself to him.

T carefully choose her outfit for his arrival picking out a sexy bra that showed plenty of cleavage. Next, came her favorite little black dress that hugged her curves just right. Hoping to give Josh easy access she skipped her normal thong and applied a nice layer of lotion to her legs so they would be soft and smooth at his touch. Selecting a sexy pair of shoes that she was able to drive in was next, T didn't plan to get out of the car until they were home but not knowing everything that turned Josh on she wanted to look her absolute best.

Once T was ready, she poured herself a drink to take the edge off her mood. Sitting down in the living room where she could keep an eye on Josh's driveway, she snapped a few pictures showing how she was dressed and what she wasn't wearing. Texting the pictures to her husband she told him, "This should be a fun night, will fill you in tomorrow." Just as she sent the text she saw Josh pull out of his driveway and head for the meeting point.

She had instructed him to park in a short-term lot near the airport. There was little chance that anyone would recognize him here and he could take a shuttle to the airport for her to pick him up. Giving Josh a few minutes head start T pulled out of her driveway and headed to the cell phone lot. Once there she checked her makeup and straightened out her dress. A few minutes later Josh texted her where she could pick him up. Feeling the butterflies in her stomach she left to pick up her virgin lover.

T left the cell phone lot and drove to the pickup lane looking for Josh's face. Spotting him she stopped so he could get in. Josh jumped into the Lexus and immediately gave T their first passionate kiss. As they enjoyed each other for the first time a police officer monitoring traffic lightly tapped on the glass and motioned for them to move along. Used to passionate greeting the officer was still perplexed at the vast age difference between the two lovers. Blushing, T put the car in drive and headed towards her house.

For the first few minutes there was total silence. Josh was so nervous and naive he didn't want to embarrass himself by saying the wrong thing. Picking up on his nervous energy T started the conversation by asking normal question about his major in school. To her, it felt odd yet powerful to be talking to him as a schoolboy. A schoolboy that she hoped would soon be impaling her pussy with his nine-inch cock. As they continued back to T's home the small talk came more freely to both of them.

Nearing their street T instructed him to duck down in the front seat so none of their neighbors, including Josh's parents would see him. Crouched low Josh finally got a good look at T's long smooth legs, he had no idea what all would happen tonight but just the sight of her legs got him hard. He was too afraid to touch but as far up as he could see there was only skin, making him even harder.

Pulling into her driveway T saw Josh's mother in the front yard, even though T knew his mother couldn't see Josh the fact that he was crouched next to her gave T a pause. She gave her a wave and an awkward smile as the door opened and she pulled safely into the garage. She told Josh to stay low until the door closed behind them. Once the door was closed Josh raised up and reached for T to embrace her again. Smiling she playfully pushed him away telling him to slow down, they had all evening and an entire house to play in.

Once inside they began to embrace in the kitchen, T guiding Josh as he clumsily pawed at her. First a strong embrace then lower until he had her ass firmly in his grasp. After a short make out session T grabbed his hand and led him upstairs. As they ascended the staircase T put some spring into her step so Josh could see just far enough under her dress to know she was not wearing anything underneath. Reaching the bedroom T instructed Josh to sit down, facing him she asked him what he wanted her to do.

Realizing that for the first time in his life that he had a beautiful woman standing in front of him that was willing to do anything he asked Josh took command of the situation and ordered T to turn around. Once her back was facing him he pulled the zipper down on her dress. Instructing T to let the dress fall down she shrugged her shoulders allowing the dress fall to her feet exposing her bare ass to Justin. Next, Josh tapped on her right foot telling T to raise it so he could remove the dress from under her foot, he then repeated the process with the left. Justin whispered for her to remain silent as he enjoyed his first closeup view of T's ass. After a few moments he reached up to unsnap her bra, fumbling as it was the first time he had ever undone one. Eventually getting it unsnapped T let the straps fall over her shoulders and grasped the cups so she wasn't completely naked, yet....

Instructing T to turn back around Josh got his first up close and personal look at her smooth pussy and could smell the aroma as T's juices began to flow. Leaning in Josh took a deep breath to inhale the intoxicating smell.

Looking up at Josh was emboldened by the sly grin on T's face as she held her bra over her tits. Taking hold of one of the straps je slowly pulled her bra off leaving her naked in front of him. Pulling T's hands down he told the MILF to stand in front of him with her hands behind her back totally exposing naked body to the young stud.

As T stood in front of him with her hands clasped behind her Josh marveled not only at her beauty but at the control he held over this naked woman. He began touching and feeling her body. T enjoyed the attention Josh was giving her body, knowing this was his first time. Occasionally she would guide him but for the most part she just enjoyed the soft touch as his large hands roamed all over her. Eventually Josh stood and T realized just how tall he was. Then placing his hands on her shoulders he guided her down to her knees so she was kneeling in front of him.

Remembering something he had read in an erotic novel Josh asked, "Who are you?"

T responded, "I am your slut Sir."

Josh then commanded T to unbutton his shirt, slightly nervous kneeling in front of the young man T reached towards Josh and began opening the buttons starting at the bottom. Being untucked the shirt fell slightly more open as each button was released revealing Josh's smooth flat chest and slightly rippled abs. T licked her lips and began kissing and sucking on his nipples. Having never had his nipples caressed before Josh's cock nearly exploded, lightly pushing her back he instructed T to remove his pants.

Leaning back slightly T unbuckled Josh's belt, before unsnapping his pants T used her nose to gently rub his cock through his jeans. Josh softly moaned his approval in response. Carefully, T unbuttoned him and while looking Josh in the eye used her teeth to pull his zipper down, her chin riding down on his cock. Grabbing the edges of his pants again in her teeth she carefully exposing the huge bulge in his shorts and nudging his jeans with her chin they fell to the floor. Repeating what Josh had done to her T had him first raise his right and then his left foot as T finished removed his jeans leaving Josh in just his boxers and socks. "Socks next." Josh commanded. T tugged both socks off leaving just his underwear. "Good slut, now remove my boxers." Josh slightly growled his next command to her.

"Yes Sir." T purred in reply. Wanting to watch as his cock sprang forward T hooked her thumbs in the waistband of his boxers. Slowly sliding his boxers down T began to unleash the massive nine-inch cock he had been hiding. T's eyes bulged as she realized not only was it extremely long but the girth was possibly larger than she had ever taken. Finally, T pulled his boxers down enough that his cock sprang out and smacked T on the cheek. "You could put an eye out with that!" T exclaimed, Josh smiled and then grabbed T by the hair pulling her mouth to his cock, T opened as he forced the massive member in and gagged her as it went down her throat.

T's gagging made Josh pull his cock out of her mouth, unsure what he had done wrong he started apologizing for gagging her. T smiled at him and said never to apologize for his cock. She explained that he just needed to give a girl time to get used to it as he was on the large side.

Taking control T got up and laid across the bed, spreading her legs she instructed Josh to get in position between her legs. "The secret to being a great lover is to take care of your woman." T told Josh as she carefully guided his lips towards her delicate areas. Slowly she instructed him to nibble on her thighs to get a feeling for what she liked. As Josh began to get closer to her pussy he got an even better smell of the aroma of sex coming from her soaking wet slit. Still closer he could taste her juices as his tongue started lapping at her folds. Guiding him into her pussy T softly moaned letting Josh know he was on target. Slowly Josh began building up an orgasm in T. Enjoying the view in front of him T was laying back, eyes closed head tilted her moans slowly increasing in volume. "Don't stop, yes, yes, yes!" was all T could reply as she felt the orgasm building.

Just a few moments later she cried "YES!!!!!!" as her orgasm rocked her, Josh was amazed at the juices that flowing from her and eagerly lapped them up. He had never tasted pussy before, but he most certainly enjoyed the taste. Josh kept lapping at her pussy as she writhed and moaned, "Don't Stop!" was all she could say. Eventually as the orgasms subsided T gently pushed his head away. Spent, she motioned Josh to come cuddle with her for a few minutes as she regained her breath. Wow was all Josh could say at his first time witnessing one of her orgasms up close. Slowly coming back to reality T realized she was with a newbie when Josh asked her if all her orgasms were like this. Sometimes, she smiled slightly blushing it depends on the situation and the person.

With a devilish grin T pulled Josh to the center of the bed, "My turn." was all she said. Once positioned she began kissing Josh all over starting with his mouth and working her way down. Reaching his nipples she gently bit and sucked on them. She could feel the monster waiting for her just below his waist and while she was anxious to ride it she wanted to make sure Josh enjoyed his first time. Finally reaching his ultra-hard cock T opened her mouth as wide as possible to take it in. Slightly more prepared this time she was able to get most of it in her mouth without gagging. Stopping before Josh was even close to an orgasm she smiled and said "That was to lube it up." straddling Josh T positioned his huge cock at the entrance to her pussy. Knowing this was the largest cock she had ever taken T slowly impaled herself on it feeling her pussy expand to accept his girth as it pushed deeper and deeper into her pussy. Josh stared in awe as for the first time he watched his cock disappear inside of the sexy MILF on top of him.

Once T's hungry pussy had consumed Josh's cock she began sliding up and down. Letting his cock nearly escape her hungry hole and then plunging it back in. Sometimes she would pull out slowly and impale herself on it as fast as she could take it. Other times she would go slow and watch Josh's face as she began to build an orgasm in him. Feeling every vein in his cock pulsating in her pussy T slowed down and toyed with him as the pressure built in his loins. Edging him she would get him close and then stop leaning over to kiss him and lick the sweat from his aroused body. Riding him like the stallion he was both were drenched in sweat and the aroma of sex hung heavy in the air.

Finally reaching the point of no return T slowed her pace, Josh reacted grabbing her hips and started slamming her up and down on his cock. Faster and faster until his cock erupted inside of her. T could feel his rope after rope of cum filling her pussy. It wasn't long before cum started to leak out of her stuffed pussy. The stimulation finally got to T and she screamed as another round of orgasms overtook her. Bucking up and down on him the young blood in Josh's cock stirred again stiffening his cock for her ride.

Several orgasms later T finally regained her senses, she could feel Josh's stiff cock still in her. It was Josh's turn to have an evil grin as he pulled out of her and moved them to the edge of the bed. Laying her on the edge he spread her legs and rubbed his cock on her swollen wet pussy. Carefully he guided himself into her snatch and began grinding in and out. A quick learner it was Josh's turn to take control watching her face he was beginning to learn when she was close, just before she would cum he would pull out and listen to her whimper and beg him to keep fucking her. Having already came once Josh was ready to settle in for a long ride of T this time, pounding her pussy he slammed his cock in and out. T's skin glistened and her pussy was on fire with excitement. After fifteen minutes of pounding T's abused pussy Josh could feel the cum building in his cock. Slamming his cock in and out even faster slammed his cock deep into her pussy as he filled it up once again. T screamed with pain and desire as her pussy stretched to accept his entire nine-inches into her burning love box. This sent T into yet another round of orgasms as she screamed in delight at what Josh was doing to her. Squirt after squirt filled her up and leaked out of her aching pussy. Finally spent Josh carefully laid down on top of her enjoying the mingling of their bodies the feel of her sweat and the aroma of sex combined with the perfume.

Tired from two hours of nonstop fucking the pair drifted off to sleep. Awaking first T snuggled into the arms of her young lover. It was dark now and she turned on a light near the bed to take in his features. The strong young man had certainly ridden her harder than she had been in quite a while and her pussy was extremely sore. Looking over at his semi hard cock T slipped it into her mouth trying not to awaken him. It was time for her to slowly enjoy her new toy and she was curious just how often he could perform in a night. With his cock in her mouth, she slowly began sliding it in and out, not deep throating it but taking as much as she comfortably could. She was rewarded with feelings of it growing harder from her touch, she continued sucking him as he stirred. Removing his growing member for just a second, she told him to lay back and enjoy. Josh smiled and propped himself up so he could watch the expert at work on his quickly hardening cock. T recognized the taste of her pussy and enjoyed the flavor of it mixed with Josh's cum slowly she sucked him while looking him in the eyes enjoying the smile on his face. Continuing her efforts T began to feel his cock stir and knew he would be cumming again soon. T began going deeper and deeper with his cock until she had taken his entire length. Josh could see T's neck bulge as she took his cock into her mouth and down her throat. He tried to hold back wanting this to continue as long as possible until finally the urge was to strong he erupted spewing hot cum directly into her throat. T gagged at the sudden filling of her throat and pulled Josh out. He continued to cum filling her mouth and then squirting huge ropes of cum on her face in her eyes and nose. As Josh shot the last of this load T could feel the cum dripping down her face.

Once Josh's cock stopped squirting T asked him how she looked, "Beautiful" was all the young man could answer as he stared in awe at what she had allowed him to do. T moved to his face and kissed him letting him taste his own cum.

Spent from the hard use T curled up next to Josh and let his cum start to dry on her body. Blissfully she drifted off to sleep snuggled in his arms. Enjoying the feeling of her in his arms Josh slowly drifted off to sleep as well knowing in his heart he was no longer a virgin.