In Kelly's Room Ch. 04

Story Info
Mom and Sis catch him with Ashley.
2.4k words
4.4
72k
22

Part 4 of the 4 part series

Updated 10/20/2022
Created 05/08/2008
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

Trevor sat at the well decorated table, nervously playing with his silverware and sipping his water. He remembered mom mentioning his birthday in regards to Ashley. He had been unable to wait another month to find out what she meant.

He was nervous when he had called Ashley, her sweet voice instantly aroused him every time. When she agreed to meet him for dinner, he couldn't believe his luck. His thoughts came back to the present as he saw the waiter walking with Ashley toward the table.

She looked even more amazing then all the times he had seen her at his moms office. Wearing a form fitting red dress, her hair let down, hanging over her shoulders. The ends resting just above her breasts. The dress was low cut enough that when she sat down, he got a good view of her tan cleavage.

"Trevor, sorry I am late." Sincerity in her voice

"Don't worry about it. I'm glad you could make it"

"I was a bit surprised you wanted to take me out. I always hoped you would ask." Her words made Trevor harder then he already was.

Trevor could only smile as he watched Ashley order a glass of white wine, then turn back to face him, her attention fully on him.

"Well, I just didn't think it was right since you work for mom and all. But I figured I would take a chance." Trevor explained

"I only work for her when I am there. After hours, I have no connections. I just wonder what your mom would think of us being here"

That's when it hit him, he didn't think about that. His mom was such a control freak, would she fire Ashley? No, she was like part of the family. But this secret rendevous after she had mentioned birthday. Oh, this wouldn't settle well with her. Another smile from Ashey made Trevor realize he didn't care.

Throughout dinner, conversation flowed easily. He learned things about Ashley he had never known. She loved the arts, but also enjoyed a night at the rodeo. A gorgeous girl that could dress like a star, but also get down and dirty. She was definitely one in a million.

Trevor could tell the wine was taking its toll on Ashley, she giggled more and showed all the signs of intoxication. The jack and cokes had Trevor feeling no pain. Sliding his credit card into the check folder, Trevor figured the gentlemanly thing to do was order a cab for his date.

Sitting next to Ashley in the cab, Trevor didn't want the night to end. First the cab would take them to her house to drop Ashley off, then to his house, where he was sure to jack off furiously thinking about her. As the cab came to a stop at the curb outside Ashley's apartment complex, he got out and held a hand out, helping Ashley to her feet.

"Man, you better walk her to her door, she is trashed." The driver said with a laugh.

"Yeah, good idea. How much to have you wait for me?"

"It's a dollar fifty a minute. But I don't think you will be coming back." The driver winked

Maybe he was right, he was a professional after all. Trevor handed him a twenty and thanked him for the ride. Turning his attention to Ashley, Trevor helped her keep her balance.

"Hey, where's the cab going?" Ashley asked

"I am going to make sure you get in your place safely. I can call another cab."

"Trevor, you are so sweet." Kissing him on the cheek. "Why did you let me drink so much?"

"How can I say no to a gorgeous woman. Plus you were having fun."

Guiding Ashley up the stairs to the second floor was a slow but steady event. Arriving at the door, Trevor dug through Ashley's small purse for her keys. His attention distracted, until...

"Well, isn't this just a sweet picture" A familiar voice broke the silence

Trevor looked up and into his mothers eyes. How did she know? She looked disappointed, a look he knew all too well from his childhood

"Mom, what are you doing here?"

"Well, I tried to call you, no answer. I tried to call Ashley, same thing. I put two and two together and looks like I was right. Go ahead, open the door."

As Trevor turned the key in the lock, he noticed Ashley looked confused and scared at the same time. Trevor reached out and caught her just before her knees gave out. Picking her up, Trevor carried her inside, his mother right behind him.

"So, were you planning to fuck my assistant?" The direct question hit Trevor as he returned from placing his date in bed

"No, I just wanted to get her in safely."

"Liar!" She snapped "Then why wasn't the cab waiting?"

"I don't have to take this, I am leaving." Trevor turned the doorknob. Standing on the other side was an equally upset Kelly. Trevor froze.

"If you want Ashley to keep her job, I think you will stay." Her words were dead serious.

Trevor turned, knowing there was no way out. Kelly entered, shutting the door behind her.

"You betrayed us. Two beautiful women who love you for someone outside the family." His mom continued.

"What should we do with our naughty little Trisha?" Kelly asked.

"Kelly dear, why don't you go in Ashley's room and find something more comfortable for Trisha. Ashley's passed out, she will never know."

"Mom, you are taking this too far." Trevor protested, almost pleading.

"No, I think Ashley needs to see who you really are. Let's see if she likes it."

Trevor slumped onto the couch, the effects of the mixed drinks faded with his mom's surprise arrival and Kelly in tow.

Kelly returned a short time later, one of Ashley's skirt suits in hand. Trevor knew there was no way out, not if he wanted to save Ashley's job. Standing, Trevor started to undress. Kelly handed him a matching pair of panties and bra that had to be Ashley's. Putting on the outfit, Trevor feared this would ruin everything with Ashley before it ever got started.

Once dressed, Trevor looked at the now somewhat approving eyes of his mother and sister. Kelly instructed him to sit. His mothers hand caressed his bare knee.

"Kelly dear, why don't you go wake Ashley and bring her in here."

Fear overtook Trevor as Kelly nodded and quickly disappeared into Ashley's room. He knew this was serious and was going to happen. His mind raced, wondering what would happen, strangely, he felt his cock get harder.

A moment later, Kelly returned, a groggy and still visibly drunk Ashley by her side. Ashley looked around the room, trying to regain her senses. When she saw Trevor, her eyes widened to a look of shock.

"What the hell?" She managed to ask. What was her date doing in her clothes and why were his mom and sister there.

"Ashley dear, we wanted you to see your date for who he truly is. We call him Trisha."

"Why is he wearing my clothes?"

"Let's just say, if you don't have a seat beside Trisha, that raise and your job won't be there Monday morning."

Trevor watched Ashley's look of shock turn to fear. How could she do this? threaten a woman's job like this. Was his mother that much of a control freak?

Ashley nodded and sat down on the remaining cushion of the couch. Still trying to absorb what was happening. Sitting between his mom and the woman of his desires turned him on even more. Kelly approached and leaned forward, kissing Trevor softly.

Trevor could not resist his sisters kiss. He had been hooked since that first day in her room. As their tongues danced, Kelly straddled his lap. From the corner of his eye, he saw Ashley watching curiously.

Kelly's hand reached over and rested on Ashley's thigh. Moving slowly up the opening of her dress. Kelly broke the kiss and leaned over to Ashley, Kissing her softly. Trevor felt his mom's hand on his cheek, pulling his face to hers, they locked in a kiss. He heard a soft moan from Ashley, she was enjoying Kelly's touch and kiss.

Trevor reached out, sliding his mom's skirt up, his hand rubbing her now wet pussy outside her lace panties. Kelly had moved from Trevor's lap to Ashley's. Trevor looked over and saw the them locked in a wild kiss, Kelly's hand cupping Ashley's breasts, now exposed.

Before he could turn back to his mom, she was pushing his skirt up, Trevor lifted his hips to let it get pushed up to his waist, Ashley looked over, watching as her panties were pulled off of her date. Kelly now sucking her nipples. Ashley wanted to explode right there.

Trevor felt his mom take his cock in her expert mouth. Sucking and slurping sounds came from the ringmaster of this escapade. Trevor moaned wildly, looking over, Kelly now had Ashley's dress pushed up and was eating her out. Ashley and Trevor made eye contact and their lips met.

The passion in her kiss told Trevor she approved. He felt her hand slide into the blouse he wore, caressing his chest, her fingers tracing the edge of the bra. How he wanted to fuck her right that moment.

Trevor felt his mom pull from his cock, she reached over and tugged at Kelly. Kelly turned and fell into her mom's embrace. As mother and daughter laid on the floor kissing, Trevor turned to Ashley. Both turned on beyond their wildest dreams. An animal instinct grew between them, Ashley pulled Trevor into a kiss, laying back so he was on top of her. Grabbing his cock, Ashley guided it to her tight opening.

Trevor pushed into Ashley, She cried out as she adjusted to his size. Her hands pushing the suit jacket off, unbuttoning his blouse. Trevor, fully in Ashley helped her pull her dress off of her extended arms and over her head. Looking down, he saw his mom and sister locked in 69. Eating each other, lost in their own little world.

Seeing that drove Trevor crazy. Turning back to Ashley, he began to pound into her tight, wet pussy faster. Ashley's legs wrapped around his waist her hands gripping the couch. Her moans louder by the thrust. Her moans made him fuck her faster. Trevor had dreamed and fantasized about this pussy for years, now it was wrapped around his cock.

From the floor, he heard the cries of mother and daughter cumming together. The sounds, the sights, the feel. Trevor couldn't hold back. With erratic thrusts, he felt his balls tighten.

"Oh fuck Ashley, I am gonna cum, oh God I am gonna cum" He panted as he tried to hold it back

"Trevor, cum in me, fill me up. Oh shit, I'm gonna cum too." Ashley cried out, his mother and sister watching.

Trevor grunted and moaned as his load filled his new lover. Ashley's legs shot straight out and her body tensed as she was over taken with her own orgasm. Her pussy tightening around Trevor's shaft.

Collapsing onto her, Trevor and Ashley kissed passionately. As they were starting to enjoy the close feeling, a voice broke the celebration.

"That's not all my dears" His mom's voice instructed.

Trevor pulled from Ashley. drained from the powerful orgasm. Slumping to the floor, he watched as his mom and Kelly moved in on Ashley's pussy. Licking her clit, tasting the mixed juices of passion. Ashley moaned louder, her freshly fucked cunt getting the attention of two tongues.

"Ashley, tell us how bad you want us." Kelly ordered

"I want it, oh fuck yes I want it." Ashley moaned, panting wildly.

"This pussy is so fucking good. Ashley you have an amazing pussy." Kelly told her as she rubbed Ashley's pussy.

"Kelly, I see your brother's ready for more." Mom instructed, noticing Trevor's cock hard again.

Kelly smiled and moved to the floor, letting boss and assistant have some fun. Kelly laid down and used her feet to pull Trevor to her.

"Fill my pussy like you did hers." Kelly insisted.

"Kelly, I'm gonna fill it good, my cock's missed you." Trevor said as he pushed into her shaven mound. Kelly gripped the throw rug, which already had traces of mother and daughter on it

Trevor fucked Kelly hard, his cock slapping her ass. It had been so long since their encounter in her room, he had ached for her pussy everyday since. The sounds of Ashley's cries and second orgasm set Trevor off. With a final thrust, he unloaded in his sister. His head exploding with emotions as he was drained for the second time.

"Oh fuck big brother, that was fucking amazing." Kelly said as Trevor pulled from her and laid on the floor.

Physically and emotionally drained, Trevor turned to his side. Watching as Kelly moved to the couch and mounted Ashley's face. Ashley hungrily took Kelly's pussy to her mouth. Licking and sucking the Trevor's cum from Kelly. Kelly moaned louder

"Ashley, oh fuck, eat me, oh you're so fucking good." Ashley could only moan her response.

Kelly began bucking her hips, her eyes closed, moaning louder to nearly a scream until she started to tremble and collapsed forward. Holding herself up with the couch. Ashley sucked happily on Kelly's pussy, taking in the flow of juices.

Trevor noticed the look of satisfaction on his mom's face as she sat in a nearby recliner. Watching. The ringmaster had orchestrated a wild night of passion between 4 people. Kelly moved away from Ashley, taking a seat at the far end of the couch.

Ashley looked down to Trevor and smiled approvingly. Rolling off of the couch, she crawled to him, collapsing with her head on his chest. Trevor watched his mom and sister get dressed. Kelly went to Ashley's room one more time and returned with a blanket that she tossed onto Trevor and Ashley.

"You two were amazing." His mom said as the door opened. "And Ashley, consider that raise even bigger now."

When the door closed, Ashley lifted her head, smiling weakly. Obviously happy about the events of the evening and her large raise.

"You looked great in my clothes" Her words surprised him.

"Thank you." Was all Trevor managed to get out

"No, thank you." Ashley sighed, with a kiss, she fell asleep, her head on Trevor's chest.

To be continued

Please rate this story
The author would appreciate your feedback.
  • COMMENTS
Anonymous
Our Comments Policy is available in the Lit FAQ
Post as:
Anonymous
5 Comments
Rapier875Rapier875over 4 years ago
To be continued.......

........never !

Shame really, as that was good.

Rapier875Rapier875over 7 years ago
Aaaaaarrrrrrrrgggggghhhhhhh !

Yet another great story that you never finished !

What is it with you that you start off, get the reader engrossed and leave them high and dry ?

Why start a new story before you finish what you started previously ?

I live you as a writer, but you are so damn frustrating at the same time !

But 4 Stars for this, it would have been 5 if you had only finished it !

God you are so damn frustrating...............

AnonymousAnonymousover 10 years ago
mom and sister a bitch

If I was him I would have told my mom an sister to get the -uck out of hear and never talk to me again but it looks like mommy sister pussy wrip him:-) :-) :-) :-) :-)

AnonymousAnonymousalmost 14 years ago
CD FUN.

I enjoyed this very much, the cross dressing adds to the excitment as the women who love sex with other women now have a woman with a hard pice of man meat

walkingeaglewalkingeaglealmost 16 years ago
Another great chapter!

Great again! Keep em coming!

Share this Story

READ MORE OF THIS SERIES

Similar Stories

"Ohhh...Mommy," I Groaned He deflowers sister, impregnates mom.in Incest/Taboo
Spring Break Wife Gary joins his mom on spring break.in Incest/Taboo
My Sister Eva Started It All Sister begs disguised brother to fuck her on Halloween.in Incest/Taboo
Making Out With Mom He gets to know his mother REALLY well.in Incest/Taboo
Sister Sucks Sleeping Sibling He gets to know his sexy sisters.in Incest/Taboo
More Stories