My Neighbour Sally's Pantie Ch.04

Story Info
Will is prepared by Sally for Riley.
2.2k words
3.79
64.1k
6
2
Share this Story

Font Size

Default Font Size

Font Spacing

Default Font Spacing

Font Face

Default Font Face

Reading Theme

Default Theme (White)
You need to Log In or Sign Up to have your customization saved in your Literotica profile.
PUBLIC BETA

Note: You can change font size, font face, and turn on dark mode by clicking the "A" icon tab in the Story Info Box.

You can temporarily switch back to a Classic Literotica® experience during our ongoing public Beta testing. Please consider leaving feedback on issues you experience or suggest improvements.

Click here

My Neighbour Sally's Panty's Ch. 4: Will Becomes Her

Will walked slowly down their stairs, his ass soar from where John had fucked him the night before. He still wore Sally's stained panties, now itching at his crotch. He reached down to pull them away before realising that he would then be completely naked, and at the will of two, obviously, randy people. Instead he shuffled down the stairs and walked into the dining room, noticing Sally cooking in the kitchen, and John, sitting at the table in his smart business suit.

"The slut has woken up" John said calmly, finishing off a slice of toast before taking a large sip at the coffee beside his plate. Will immediately reached up to cover his pride behind the panties, then dropped his hand, realising John had seen all that he had.

"How's you ass today?" John asked.

"Soar" Will replied, again feeling where John had stretched his anal hole, penetrating and ejaculating into his rectum.

"Want me to lick it better?" John asked, pushing his chair away from the table. Will looked at Sally who stood nodding, still not looking up from her cooking. He walked slowly forwards, dropped the dirty knickers and lent over his legs, allowing his limp cock to rest between John's legs.

John bent over Will's body and pushed his tongue into Will's crack, licking over the red entrance passage. Will did feel the immediate effect as the soar throbbing pain eased away under John's gentle, knowing, touch. He felt his body begin to relax, and his cock start to stir, pressing against John's trouser leg.

"Easy tiger, I don't want you staining my work trousers" John said easing up.

"Here Will. Hold this against where it is soar" Sally suggested, entering the dining room. John released his grip on Will's ass cheeks and let him stand. Sally stood facing them, an ice cube in her grip.

"I can't put that there" Will protested. Sally grinned and reached into her pocket, pulling the top of a Polaroid out, the one where Will was penetrated by a cock.

"A lot worse has been there" she replied, again, pushing her hand out with the ice cube in. Will tentatively reached out and took it, touching it hesitantly against his ass cheeks. Sally stepped forward and pulled Will against her body, gripping his ass cheeks. She took his hand, seized the ice cube and pushed it into Will's anus hole.

Will screamed as the searing cold pierced his body, bolts of pain exploding around his ass. Finally, his body heat began to melt the cube away, cold water dribbling down his crack and resting against his balls. He felt the last of the cube melt away and flow either into his rectum or down soaking his testicles.

As Sally had promised, the ache felt less, the cold water easing away the pain.

"What do you say?" Sally asked removing her hands.

"Thank you" Will said.

"Your welcome. Now, Riley is getting back later today. And you have to be here" Sally said wiping her hands on her clothes. Will stared in horror at the mention of Riley, Sally and John's son.

"If Riley sees me, there will be trouble" Will said panicking, searching for the knickers.

"John and I are going out tonight. I'm going to prepare you for Riley then it's up to you to seduce my son. When I get home tonight, if I don't here some action, well, you know what will happen" Sally explained, again, pulling the edge of the Polaroid out of her pocket.

"Ok" Will said.

John left for work a little while later while Will was ordered into the sitting room, with two slices of buttered toast and a glass of fresh orange juice. He tried to eat the food, yet his only thought was of tonight.

Riley had gone to the same college as Will, although Riley had been very popular with the girls. He wasn't liked much by the guys, but he had a way of talking a girl into bed and still remaining friends with her the day after, but never going beyond that. Many thought Riley was gay, sleeping with girls to repress his desires, but Will had always thought he was as straight as him, or as straight as he thought he had been.

And yet tonight, he would have to find a way of talking this man into bed while wearing his mother's panties.

Sally walked in, dropping a bundle of clothes and make up onto the sofa beside Will. Will slid a bit further along the sofa, allowing Sally to sit beside him. She turned to face him, reaching for her make up kit.

"Ok Will, take off my knickers" she began, setting the open kit beside him. Will slid the used panties off and placed them on the table top, sitting in front of Sally with his small limp cock resting between his legs, and fully exposed to the outside world as the curtains stood open.

Sally looked down at his resting member and smiled, stroking the back of her hand against it for a few moments, before facing him again. Will felt his cock stir slightly but didn't react as he had hoped. His cock pushed out maybe an inch.

"Now I know many of your 'friends' call Riley gay, but Will, your not straight yourself" Sally said, taking a lipstick from her pack, and pulling the lid off.

"Now, I know Riley is just like any other male. The amount of time's I have seen him wanking through the crack of his door over my panties or his 'secret' stash of magazines" Sally said, trailing off slightly.

"Have you ever had sex with him?" Will asked curiously.

"Sex with my son? Are you crazy" Sally almost shouted. Will was taken aback with this, withdrawing slightly from her.

"I'm sorry" he tried to apologise.

"How I have imagined fucking the brain's out of him, but he doesn't show interest in me" Sally said, a grin appearing on her face. Will relaxed slightly, but still he couldn't get a hard on, and save face in front of this women.

"But I have found a few gay DVD's in his collection, amongst other things" she said laughing slightly to herself. Will grinned nervously, again looking out the window as people continued to pass, no one so far looking in.

"And I want you to be his first gay partner" Sally demanded, gripping the back of his head with her meaty hand and moving the lipstick slowly over his moist lips. Will waited until she had finished applying the make up, before pulling away, pressing his lips together to smooth the make up, like he had seen his mother do.

"I'm not gay" Will protested softly.

"That's not how it seemed last night when my husband had his cock up your ass! But let's just say your curious ok, and you will make him curious as well" Sally said, packing the lip stick away. Will nodded, smelling a fishy scent in the air. He reached down and pulled his foreskin down, wiping the old white cum away with his forefinger. He moved to wipe it off before Sally gripped his hand and pulled his finger into her mouth, sucking it clean.

"Tasty" She said grinning, releasing his clean, wet, finger.

She pulled some clean satin blue knickers from the pile and handed them to Will, who began to pull them up. They were Sally's and therefore rather large, although still stretching a bit around his crotch and ass, sliding up slightly.

"Now Will, I want to talk about your mother a bit" Sally said, looking at Will.

"Ok" Will answered, swallowing hard.

"You must have seen a few things. I want you to tell me one of her dirtiest secrets" Sally asked, handing a wrapped tampon to Will. He ripped the gold outer plastic off revealing the woollen tampon inside.

"If you don't, you know what" Sally stated.

"Well" he began to say then stopped. He couldn't tell Sally what he had seen once, and heard many times since. It could ruin his mother if Sally revealed this to the outside world.

"Tell me" Sally said bringing out the photo.

"She likes to get spanked" Will revealed quietly, holding the tampon in his hand.

"Roll over Will" Sally instructed taking the tampon. Will nodded and rolled onto his stomach, feeling Sally push the tip of the tampon against his anal hole.

"I'm going to insert this into your ass to soften your ring for Riley. What did you see?" she asked, pushing the tampon into Will's hole. Will felt a slight ache but his hole had been loosened by John and the ice cube. So now he just accepted the pressure.

"I came down to breakfast one day when I was ill from college. I had heard he front door open so assumed my mother had a visitor." Will began, feeling the entire tampon in his hole, the white string hanging out along his crack.

"I looked in curiously and saw... the mailman sitting on her office chair, my mother naked over his lap being spanked." Will revealed, noticing the look of sheer delight on Sally's face.

"I was about to throw him out when I heard my mother cum from his slapping. I was in shock, and stepped back. Since then, he often visit's when she doesn't know I am about" Will finished, turning onto his back again. He sat there, open legged with a string hanging from his ass, exposed completely to Sally.

"Thank you for your honesty Will. I will not ask you any more. Now, pull these on" Sally instructed handing him some nylons. He pulled them up, enjoying the feeling against his skin, until they covered his knickers and tampon filled anal ring.

Sally pulled a tight black leather skirt up Will's legs until he was dressed, from the waist down at least, like a cheap little tart, sitting with make up on, ready to fuck a person he had gone to college with.

Will put his legs back on the floor, feeling the slight discomfort with the tampon pushed in. Was this what women felt every month during their periods?

Sally reached around Will's body and pulled a silk white shirt onto Will, buttoning it up securely. She reached down and took some large heels from the pile, sliding them onto Will's feet. Will accepted all of this, completely at the mercy of this woman.

"Now stand up and pose for me" Sally said taking her camera. Will nodded and stood, standing at a polite pose despite being dressed as a slut in make up about to seduce a man. Sally took the photo.

"Now sit down, spread your legs for me, pull your skirt up a little" she instructed. Will nodded and followed her instructions, again holding still as she took the photo of him.

"I think your ready for him now" Sally said, taking the clothes and leaving the room.

Will sat in limbo for hours, dressed as a woman to the outside world, the door locked, so he couldn't leave. He thought of closing the curtains then realised that Sally could punish him for that. So he sat there. He was served lunch but continued to sit there until 5 that evening when Sally unlocked the door and walked in, dressed in an evening gown that was hardly flattering to her large frame.

"Now Will, Riley will be back shortly. I am meeting John for a meal. Remember our agreement and tomorrow you can return to your normal life" Sally explained. What normal life? Will thought. After tonight, he would have done something he hadn't thought possible, actually seduced a man.

He was left there until he heard a key turn in the lock, and realised his night of passion was about to start.

"Hi mom, I'm home" Riley shouted, his voice carrying through the room.

Will heard Riley walk up the entrance way, passing the door as he hung his jacket up.

"Hi mom" he said, Will realising that he may have seen someone dressed as a women assuming it was his mother. Will turned to face him. Riley walked into the room and froze, staring at Will dressed up in his mother's clothes.

"What the fucking hell is going on here?" he demanded, his hands closing into fists.

"I know your gay Riley, and I want you" Will said, standing, his skirt still hitched up and the edge of the blue satin panties exposed to him.

"Why the hell are you dressed in my mother's clothes?" Riley asked, stepping towards Will, still ready to attack him. Will walked slowly forwards, placing his hands on Riley's shoulders.

"Your mother knew and prepared me. She wanted me to be your first?" Will said, massaging Riley's shoulders. Riley stopped talking, taking in what was happening, as a man came on to him.

"Prepared you for what?" Riley asked softly as Will unbuttoned Riley's denim shirt, letting it hang open, exposing Riley's well muscled stomach.

"To fuck you!" Will stated, gripping Riley's chest and pulling him against his body, kissing him.

To Be Continued...

Please rate this story
The author would appreciate your feedback.
  • COMMENTS
2 Comments
bigrimmstalesbigrimmstalesabout 15 years ago
o dear...that was a bit of a spelling gaff!

I am trying to make my arse fly but it won't take off, more gets drilled into the floor. That really spoilt what was in essence a great story trying to get out..Can I suggest use an editor?

AnonymousAnonymousabout 16 years ago
Learn to spell.

Please. Sore in this context is sore, not soar. "Soar" is what eagles do.

Share this Story

Similar Stories

Linda's Discovery Mom discovers her son's secret.in Incest/Taboo
Accidents Happen! A brother and sister make a discovery.in Incest/Taboo
Nasty Little Sister Coed sister has had enough! She wants some pay back.in Incest/Taboo
Costume Sex Brother and sister are confined together in their underwear.in Incest/Taboo
Sucking Amy's Panties She catches stepdad sniffing her undies and makes him pay.in Incest/Taboo
More Stories