All characters are 18+ and not based on any actual person.
******
Monday morning to Monday evening
Billy Rollins was having a pleasant dream, he was remembering how he had lost his virginity. His Mom had been thinking that it was long enough for an 18-year-old boy to be a virgin, and had sent him next door to the neighbor's house, Madison James, the young divorcee, to supposedly help her with some housework.
When he got there, some innocent flirting and suggestive talk was all that was needed to get it going. Madison knew that Billy had been looking at her through her bedroom window, which was right over the fence and facing his bedroom window. She had smiled as she got home from her job as a nurse, and had stripped naked at the window, supposedly unaware that he was watching and probably pumping his prick. Now, she was going to tempt him into the sack and claim his cherry.
And claim it she did, her mouth milked out the first fast spurt, then with him between her thighs, he fucked her to orgasm, and keeping him held tightly, she rolled them over, her talented cunt muscles stroking him, keeping his cock hard and eager, and she rode him to a thunderous orgasmic explosion, making Billy's first time the one he would always remember.
The dream shifted, his 19 year old sister Brianna naked and was welcoming him, spreading her thighs open, the V of her pink pussy glistening with heated juices, he was iron hard as he took position, so ready to drive it in....
Drrr...Drrr...Drrr...
Billy's eyes opened, the glorious vision disappeared, and he grunted as he awoke. Damn cellphone, it was not even 7 AM, who the hell was calling at the time of the morning?
He didn't notice the caller ID as he grumbled out ''Hello?"
Madeline's voice purred out at him, "Good morning, Billy, I hope I didn't wake you up."
His mouth went dry, holy fuck, it was...was...."Maddie?"
"I love it when you use my name, just like you did when you fucked me, and called me Maddie when your cock was exploding deep inside me. It makes me so excited knowing that you watch me masturbate. Now, fair is fair, bring yourself over to the window. I want to watch you stroking a big morning hard on while you watch me get myself off.''
Billy quickly did so, bringing himself right over to the window. He looked out, oh fuck yeah, there she was, the bed was in the perfect spot, and he was looking right between the spread of her thighs, her pussy was clean shaven, so hot, so inviting, god, he'd had his cherry popped by that sweet snatch laid out before him. The window in his room was one of those big floor-to-ceiling types, she'd be able to see all of him.
Maddie could feel her breath catch, Billy's cock was so nice and big, a real cunt pleasing tool. It sure had pleasured her, to feel his young, eager cock take the plunge, it made her thrill to think that she had taken his virginity. His balls were nice and big, full of a juicy load, mmmm, she wanted to see that load spraying his window as a tribute to her.
"Now, let's do it together. I'm putting my phone on speaker, so I can use both my hands!"
She giggled, and said, "You do the same Billy, and I want you to cum real hard for me, I want to watch your cum splattering all over your window! Now, let me give you some hot viewing! I love stripping naked, knowing that you are watching me, and stroking that big hard cock, the big, hard cock that filled my mouth then fucked my hot cunt.''
Billy watched, his heart pounding, as Maddie's fingers started to dance all over her body. Her eyes remained fixed on him, staring at his swollen cock. Billy quickly joined in, slowly stroking his stiff cock, knowing that once he got into a serious stroke, he'd be done.
Maddie watched his hand start to shuttle up and down his prick, which made her drool. Remembering how well her holes had been fucked, and watching that very same prick that had vented his virginity upon her, made me head spin with lust. The fingers of her right hand slid down over her mound, she reached down and peeled her lips apart, letting Billy gaze at the hot, shimmering pinkness. Two fingers slid slowly up inside her, her breath catching in her throat as she played with her body.
''Mmm, mmm, mmmmm, oh that feels so good. How do you like it, Billy? Tell me!''
''Looks so fucking hot, god I love to see you getting all hot!''
She flicked at her clit, shuddering, then she brought her vibrator up, smiling through the window at Billy.
"Now, I'm going to ram myself, pretending it's your cock. Hang on to it until I cum, I want to see you spray your window baby!''
Billy could hear the buzz as she switched it on, then she brought it to her pussy, and powered it in with a single thrust. Her loud cry of pleasure filled Billy's ears as she watched the sexy neighbor pleasuring herself so wantonly, starting to pump her vibrator in and out, plunging deep as she stood with her legs apart, watching Billy as he stroked his rod.
"So close, so fucking close, stroke that big cock, do it hard, cum all over the window!"
Billy did so, and Maddie's voice howled, ''Fuck, oh fuck, cumming fuck yes, YES!"
Her body was writhing in orgasmic bliss, her eyes still fixed on his cock and he erupted. Maddie saw him arch his back, hand flying up and down his prick, grunting and growling, and watched streams of cum gushing, splattering his window. That propeled Maddie into a second climax, her dripping fuck hole clenching and unclenching in orgasmic rhythm at the buzzing vibrator, feeling like an overheated live fuck doll, shrieking and howling, god, she was cumming like a train.
Drifting down, Maddie purred, "Mmmm, that was so nice, Billy. Be watching me tonight, I'll have a nice surprise for you, see you then!"
Builly staggered back to bed, his legs were rubbery, and he flopped back onto the mattress. The window was splattered with 10 solid ropes of spunk, god, he'd really creamed that glass. And Maddie had something even hotter planned for tonight? Oh fuck, he couldn't wait to find out what it was.
*****
As Maddie went towards the bathroom, she smiled. Maddie had arranged for Billy's Mom, Gayla, to come over after work. Maddie had been getting strong messages that Gayla was interested in some lady loving, and she was going to do her best to seduce her and pleasure her on her bed in full view of her son. Mmmmm, when he sees both his Mom and me, bet it'll make him go crazy.
Under the hot spray of the shower, Madison needed one more expolsion, she buzzing of her vibrator filled the room as she drove it up he creaming tunnel and fucked herself with power filled plunges, she felt like an overheated teen slut, and she shuddered and squealed in bliss as another orgasm washed over her.
*****
He was by the window, watching closely. Maddie's car pulled into her driveway at the usual time, coming home from work. His cock was like a steel hard pole, just from anticipation.
*****
Maddie greeted Gayla at her door. After Maddie had called her from work and asked her to come over to her house when she left work, she had been waiting for a couple of minutes. The front porch of the house was out of view, so Billy had no idea what was going to happen.
Gayla grabbed her, and their mouths came together in a heated, lust-filled joining, tongues twinning together, letting the lust ramp up. Maddie's suspicion that Gayla was hot for some lesbian action had just been proven.
