Mrs. Glover's Daughter Ch. 01: Caught

I've lived next to the Glover's my whole life. They are practically my second family, I have a key to their house, and I can basically do whatever I want over there. They are a great family. James and Abby, then their son Donald.

We live in a small town bordering Lake Tahoe in Nevada named State Line. Donald and I were born the same year, and went to school together all the way through our undergraduate degrees. From Zephyr Cove Elementary to UNR we stayed next to each other. Of course growing up in the mountains we both grew up skiing, but somewhere around sophomore year of high school Donald started getting more and more into football. He was a mixed race god, 6'4", muscles in places you didn't know muscles existed. I stopped growing at 5'6" and stuck to skiing and swimming. I was able to get a partial scholarship to go down south and swim competitively. He played wide receiver, and was good enough to get a full ride scholarship to play with the Wolf Pack. It was actually Abby who convinced me to follow Donald there, she said "Come on Chris, you two grew up together, you took baths together as kids, you dont want to take your first steps of adulthood with him? He is really iffy on going to UNR, if he knew his best friend, well brother, was going there too? I might just make him go."

Well, this is the first year in school that we had spent apart. I went on to get my masters at the University of Oregon, and Donald was a red shirt senior for UNR. He went into the draft but went un-drafted. He has an agent, and I'm sure he will and somewhere, but he also has his degree, so Im glad he has a back up. Unfortunately this week him and his family are heading up state for a two week long family reunion. So I sat there in my room, on the second story of my house. My head trying to fight off sleep while i stare intently on the mini-van parked in the driveway of the house next to mine. Our houses were almost mirror images of each other and so I had a perfect view into their driveway, and the master bedroom.

I've had this crush on Abby since I was 13. I was staying the night when I walked in on her masturbating in a nice stocking and garter set she needed to wear at work. She looked amazing, and that was easily my first real sexual experience.

I started thinking about the way she looked as she stroked her clit, and I fell asleep. Dreaming of a day she could tell me she has always liked me too. She is a 5'8" skinny white girl, with black hair and brown eyes. Her body is amazing, perfect boobs, long legs, and just a sensual feel to the way she exists in the world. I've always dreamed about her lying in bed, legs spread, waiting for me. I have an unhealthy habit of spying through her window while she changes, and that really fuels a lot of my deepest desires.

I was jolted awake by the sound of a minivan speeding into the distance. I look at the driveway to see a missing mini-van. I look back to the house to see lights turned on in the living room. That isn't a shock, they usually leave the on a timer to prevent home intruders.

I make my way down stairs, across my yard, and over to the window of their living room. No one. I walk over to the front door, take out my spare key, and open the door. Right in front of the door when you walk in is the staircase that leads to the master bedroom.

I turn on my phones flashlight and head upstairs.

Once I get to the room, I just look around. There is a large king sized bed with nice oak bed frame in the middle of the wall on the left of where the door enters the room. The darker purple satin that adorns the bed really embodies the sensual feel that Abby exudes. Across from the bed and on the wall to the right of the door was a large oak dresser with 8 drawers, 4 on each side. Next to the bed were lovely nightstands with two drawers each. Other than that there was a lot of free space in the room, it didn't feel empty, but like there were spaces that were designed to be there. I walked into the room and look back at the wall the door is on to see another door to the left of it that lead to the master bathroom. It was a nice bathroom. It has a shower, a bathtub jacuzzi, two sinks, a separate room for the toilet, a bidet. Fancy stuff. To the left of the dresser is another door that leads to their walk in closet.

I head over to the dresser and quickly figure out that the right side belongs to Abby. I search through all of the drawers looking for any lingerie I could get. I grabbed a few pairs of underwear, but I couldn't find any actual lingerie. So I head over to the closet and head in. My flashlight illuminated the small walk in closet. The room was really organized, with heels in a rack down the middle of the back wall, everything else was in hangers, or in labeled bins. I walk over to the heels and take a look at them. I chuckle looking at the size. 9.5. Im an 8 in men, so me and Abby have the same foot size. I start shining my light around the closet to see if I could spot anything. Right against the wall on the left side of the door was a black and white material. I quickly walked over to it and pulled it down. It was a maid outfit. My jaw dropped and my dick got hard immediately. Everything was on the hanger. The stockings, the garter, the hat, and duster, and even satin gloves. I took the hanger out of the closet and layed the dress down on the bed across from the door to the bathroom. I took a step back and just imagined Abby wearing that maid outfit. I pulled out my dick and started to stroke it. It was rock hard, I just wish Abby wre here wearing it.

My head starts to tilt back as I imagine the fabric draped on her skin. Then the light turned on and I jumped. My head shoots towards the door and Abby is standing there smiling, trying to hold back a giggle.

"Oh Chris... you are really cute." she chirped.

"Wh...What?!.." I muttered, still taken aback as to why she was home. "What are you doing here?!"

"Oh, you mean why am I not in a mini-van with my husband and son halfway up the state right now? Well, Donald and I are going to be flying out tomorrow. The van had too much stuff in it, so we decided to book last minute flights and have James pick us up there."

"Oh..." I look down, covering my cock which was now soft strictly out of shame.

She strides over to her nightstand and opens her top drawer. In her heels she is so much taller than me, but I'm not complaining, the way she bends over the nightstand was really nice. I could feel myself getting hard again, but then felt that same shame swept over me. She grabs something out of the drawer and puts it behind her back. She struts over to me with one hand behind her back. The black dress she is wearing perfectly adhering to her curves. Her eyes both soft and cold at the same time.

"I'm going to need to punish you." She exclaimed as she walked over to me. I look down as she approaches me. She pushes my chin up so im looking at her in the eyes, takes her hand off of my face, smirked, and kissed me. Right as her lips came in contact with mine, my hands rose to her face, and I could feel a cold metal device placed around my cock.

I backed up in shock. "What the fuck?!" I yelled in response. I look up to see a devilish grin on Abby's face.

"Oh I've waited so long for this." She whispered.

"WHAT?!" I immediately chimed back.

"Oh you don't think I see you jerking off your little cock to me just changing? I bet you like this don't you?" She turned around and lifted up the back of her dress showing off her perfect ass and red g-string. I could feel a pressure on my cock, but it just can't get hard. She smacks her ass and lowers her dress back down. "You're going to do everything I say, or else I;m telling everyone about quite few things. Spying on me, breaking into my house to jerk off to my lingerie? Hmmm... you'll be a creep forever."

She was right. If all that got out into the community I couldn't come back. And believe me, this community is connected. It would be hard to escape.

"What do you want?" I say somberly.

"I want you to say that again but this time say ma'am at the end." She sits on the bed and crosses her legs.

"...What do you want... ma'am?" I get out, my words dripping in shame.

"Go take a nice long shower." she commands.

I look at her. "Really? Thats it? You want me to take a shower?"

"Yes, now go. And say yes ma'am when I give you an order."

"Yes ma'am." I say as I walk into the bathroom.

"HEY!" She yelled. "Thats wrong, you look me in the eyes when you say yes ma'am, then you go."

I turn around and see her legs spread open with her fingers rubbing her pussy. I was shocked and couldn't get anything out.

"Well." She said impatiently. I could feel my cock trying to gt hard, but not being able to under the metal. "Look me in the eyes."

I look at her eyes and say "Yes ma'am." and turn around into the bathroom. Once I shut the door I fall to my knees, this is both exciting and awful. I have no idea how to feel.

I got up and walked over to the shower. I turned it on, striped down and got in. I swim on a regular basis so I'm pretty lean, and completely shaven. I try to beat my own records, and to be honest, it just feels cleaner. Once I got into the shower I looked around for soap, but the only thing I could find was Summers Eve. I looked around a bit more hoping that there is other soap, but no. Nothing. I grabed the bottle and squirted some out on my hand. I started washing my body down and trying to distract myself from the situation at hand.

While I was soaping up the door to the shower opens up and a completely nude Abby walked in to the shower. I gasp quickly and then look at her amazing body.

She shushed me and proceeded to grab me from behind and rub the summers eve into my skin. The feeling of her rubbing me made just felt right. She had electricity in her fingertips and she made me feel amazing. I slowly closed my eyes and let the water fall on me. One hand glided its way across my hairless stomach to my crotch. and right as I could feel her touching my dick she starts kissing my neck and she slid her other hand back so her middle finger is right on my asshole.

I jerked from the shock of her finger. and she shushed me again. "Do as I say. This isn't your asshole anymore. This is your boy pussy." And she put pressure on my hole. I let out a small squeak as her finger opened my hole a little. "Good girl. You're already making noises like a slut." She opens the summers eve and puts it on her hands, she quickly spun me around so she was embracing me. I could feel her hands on my ass cheeks already, and slowly slid their way towards my hole as they lathered up the soap.

She stopped with her middle finger on my hole and looked me dead in the eyes, and sayed "What is this?"

and I looked at her, shame washing over me, almost unable to speak. I could feel tears coming to the surface as I sat there with the words on the tip of my tongue.

"a boy pussy ma'am." I said, and she slider her finger into my ass as she pressed her lips against mine. I let out an unintentional moan as all of my muscles clench up, but soon her tongue sliding against mine made me loosen up, and she started to move her finger in and out of my boy pussy.

"Yeah, you're liking that are't you?"

"Yes ma'am." I said as I rested my head on her chest gasping with every thrust of her finger into my hole.

"Good, because we need to clean you out." She said as she slid another finger in, and I let out another sharp squeak. "Get on your knees and press your face to the floor."

"Yes ma'am" I said and lowered my body down, her fingers never leaving inside me. As my face presses against the floor I could feel her stretching my hole open with her two fingers as she shoved them in and out of my boy pussy so water could get deep into my hole. She forced me to rinse out my boy pussy until it was completely clean. Once she was done she took out her fingers and put them in my mouth.

"Meet me in the bedroom." She said as my tongue caressed her fingers absent minded. She then got up and waltzed out of the shower leaving me there with my ass in the air.

I got up, turned off the shower, got dried off, and walked out into the room to see Abby coming out of the closet with a few items.

"Alright, lets have some fun." She said, and grabbed my hand. He immediately stuffed me into the maid outfit. It was form fitting to the torso, but the lower half of the dress poofed out and provided plenty of room. Then she took me over to another station where she had several nail polishes out. She grabbed a simple red and painted my fingers and toe nails. The polish too a minute to dry so while that happened she lead me over to her desk where she bent me over, and grabbed a small metal object off the bed. I could feel the cold lube drip out onto my boy pussy. I clenched my jaw and I felt steel press up against my hole. "Relax." She commanded. She slowly made her way all the way into my ass until the metal object was sucked up into my hole.

"What was that??" I said gasping for air.

"Take a look." She smirked as she pointed to the mirror on top of the dresser. I turn around and spread my ass cheeks to see a red jewel sticking out of my boy pussy. "It's an anal plug. From now on you are no longer Chris, you are now Chloe." As she said that I could feel my dick try to stiffen.

She then sat me down and put my hair into this net, and grabbing a tool box shaped object. Over the next 30 minutes Abby sat there and applied makeup to my face. A black eyeliner, red lipstick, smokey eyes.

Right when she said I could open my eyes she put a wig on my head. A straight black wig. As I stared into the mirror looking at the girly boy sitting on that bed, Abby was pinning the wig to my head. She then puts the headgear on over the wig, and kisses my forehead.

"Alright your nails should be dry, lets get you in some stockings baby girl." I could feel my asshole quiver when she called me baby girl. I didn't know what was going on with me.

She strapped a garter belt on under my dress, and slid on some mesh stockings that had really intricate designs going down the back. The next thing she did was grab a nice black and white lacey thong and slid it up my legs so that it rid up and put pressure on my plug. I let out a small moan as she slapped my ass and threw a pair of black heels on the ground at my feet. They we 6 inch heels with a bow on the front. "Put em on Chloe, then you're almost done."

I bend over and put the heels upright on the floor and step into them. Immediately I can feel my ass push the plug in further as I look in the mirror to see a sissy maid. I looked like a girl, flat out, I could go to school like this and I would be hit on so often. Not even Donald would recognize me. And just as I had that thought I hear Abby yell out "DONALD."

My head snaps in her direction, and my eyes widen in a face that says please no. But it was too late, I could already hear him walking up the stairs.

"You do not speak, you only make noises." She snapped at me. "You don't want to know what happens if you speak."

I gulp. I hear the door start to open, my boy pussy clenches, my stomach drops and I look over to see my best friend standing in the door, shirt off, waiting for his mom to tell him why she called him.

"What is it? Who is that?" He asked

"Well this is my present to you for graduating. It's called a cum slut."

"What?"

"Just sit down and let mommy show you." she said staring at me. And he did, he sat down on the bed. "Chloe, on your knees in front of my son."

I stared at her, not wanting to move. "Now Chloe." She said in a harsh tone.

I walked over and got on my knees in front of my best friend, I was about to do something I had never in my wildest dreams imagined I would be doing.

"Look into my sons eyes Chloe." She commanded. My eyes drifted up from his crotch to direct eye contact with him. "Rub his crotch Chloe."

I took a big gulp and placed my hand right on his dick and started stroking it with his eyes staring into mine. Abby came up behind me and started whispering in my ear, "Keep staring in his eyes you sissy faggot." Her hand slid down my back and under my dress where she grabbed the gem on my anal plug and started playing with it. She moved it so my boy pussy stretched around the shiny metal. I let out a quick moan as she started playing with it. "Yeah, you like when momma plays with your little boy pussy. I've been grooming you for this you stupid faggot." I let out a few wimpers as my ass starts to move with her hand movement making her pull out more, and push in deeper. I could feel my boy pussy starting to pulsate as i stroked Donald's cock.

He bit his lip says "Pull out my dick Chloe." When he says that I could see the sexual desire in his eyes. He wanted me. I knew when he spotted a target all through our life, and now it's me. My eyes glisten in the light as i think about the fact that someone I consider my brother is telling me to pull out his dick... and it was making me horny.

Abby leans into my ear again and says "You were born serve his cock... do your fucking job." and she spanks my ass hard. I let out a moan as the sting settles on my right ass cheek. I reach into his pajama pants and pull out the massive hard cock. I had no idea that his cock was this big, it had to be 8.5 - 9 inches of cut meat. I put my hand on it and feel how it is rock hard right now. I make eye contact with Donald again and start to move my hand up and down on the shaft of his cock.

I could feel my own sexual desires boiling up inside my core as I stroked his fat dick. I had never realized how much I wanted to serve Donald and Abby. I moan as the anal plug is taken out of my pussy again and slid right back in. And as I'm having this moment of pure sexual realization I lick Donald's cock from balls to tip, and then put his cock inside my wet mouth. I made my tongue circle around the head of his dick as i slowly make my way up and down on his shaft. Abby takes out the butt plug and starts to finger my ass, she puts in three fingers, and my back arches as I let out a sissy moan. I slide my mouth down as far onto Donald's cock as I can. I can feel the precum dripping down the back of my throat and its making me hornier. I start going at his cock, trying to service him as best as I can. I lift my mouth off of his cock and start licking the soaking wet shaft up and down while staring my best friend in the eyes. Just then Abby grabs my neck and stands me up, turns me around, and says "Sit."

I take the hard, wet cock of my best friend and place it against my boy pussy lips. I could feel the pressure, I could feel it wanting to slide in and get shoved deep inside my ass. I slowly made my way down, squealing as his cock separated my asshole and slid inside me. Before I knew it he was balls deep into my boy pussy, and he had no idea it was me... I kinda wish he did.

"MMMmmmm yeah, youre a good little whore aren't you?! You like my cock inside you like that dont you?" He started to say while laying back on the bed with me sitting on his lap. My mind started to go crazy. Why was I so horny after he called me a whore?! My mind was racing, and while everything was a blur my ass had started moving up and down on Donald's cock.

"Oh yeah, you slut. You wanna take this cum dont you? Yeah, use that pussy to get my cum you whore." I started going faster with every word he said about cum. My moaning started to become uncontrollable, and I found myself really wanting his cum.

As my ass is being fucked hard I let out a "Oh god yes." and Donald grabs my hips and shoves me deep onto his cock and holds me there. He reaches around to the front of my dress and feels my cock cage.

"WHAT THE FUCK?!" He says. "MOM! Is this Chris?!" He grabs my face and makes me look at him.