Grace's Covert Humiliation Ch. 03

"I really liked your pictures. You are so hot."

"Thanks. I'm glad you liked them. In what time zone are you?"

"Eastern time."

I thought, clearly whoever I was chatting with didn't want Sadie to know that he was local.

"Hey is Sadie your real name?

"Of course not. I have to be careful."

"What's your name?" I typed.

"You can call me Kyle. I'd rather not use my real name either." I almost laughed at the choice of pseudonym despite myself. "You are so hot," he repeated. "I liked the pictures of you sitting in the chair. You are so sexy. You almost look like a model or something. I've wondered what you look like without your clothes on. I'm glad you let me see that." It was a mistake for "Kyle" to indicate that he wondered what "Sadie" looked like without her clothes. I decided it would be suspicious not to call him out.

"What do you mean you've wondered what I look like without my clothes."

Another minute long delay, then, "I mean that I saw the pictures of you in your clothes and bikini first. So I couldn't wait to see the other pictures."

"Oh. Okay- that makes sense. How old are you Kyle?"

"Thirty-six." I knew this couldn't be true. "Hey, could you send me some pictures without your face blurred? I promise to keep them to myself. I'd really like to see your face."

Now I paused. "Let's see how the rest of our conversation goes first."

"Okay. That's fair. Can I ask you something? You don't have to answer if you don't want to. Why do you like to expose yourself?

"It turns me on to think about people seeing me. I'm very modest but since no one will know who I am, I'm safe with the fantasy."

"So it's a fantasy of yours for people to see you. Do you mind if I say what I think of your pictures?"

"Yes, please do."

"Well first you look so in shape and hot. You look like a model. Your legs are smooth. I love the way the lower part of your tits curve up to your nipples and I love the way your nipples stick out. I like the curves of your butt and low back too. It really looks like a model. I'm not sure how to say this part. I like the part between your legs. It makes me want to touch you."

Based on this last message, I was pretty sure I was communicating with Wilton rather than Jonathan. Either that or Jonathan was intentionally trying to present himself as someone who expressed himself awkwardly. But that didn't seem like something he would do.

"Thanks Kyle. That's so nice of you. It turns me on to think of you seeing me."

"So would you send me some pictures with your face?"

"You say your located in the Eastern time zone? Where do you live?"

"New York."

I sent "Kyle" three pictures of Grace with her face unblurred.

"Wow. That's what I thought."

"What do you mean?"

A substantial pause. "Your face is just the way I pictured. You look so pretty smiling without any clothes on."

"Thanks Kyle. You are turning me on."

"You like to show yourself to guys. What else do you like? I mean about sex."

Here I paused but thought rapidly, an impromptu plan forming.

"Well, there is something else I've fantasized about. But something I've never told anyone. I suppose I can tell you since we'll never know each other. It's unusual.

"Yes please tell me.

"I imagine myself sound asleep in bed. A man comes into my room. He's careful not to wake me up. He touches me and then he takes me, coming inside of me. Later I wake up and realize that someone has filled me but I'm not sure who. The mystery of who it could have been is such a turn on for me."

"I can help you," can the instantaneous response.

"That's the idea," I thought to myself.

"It's important for me that you not learn who I am though, Kyle. I don't see how we could manage that," Sadie typed.

There was another long pause. "What if you went somewhere and checked into a hotel? You could give me your room number and leave the door unlocked?"

"That's an interesting idea." Sadie typed. "You'd have to travel a long way from the East Coast though."

"That's okay. It would be worth it. I'm also worried though."

"What are you worried about?"

"I don't want you to see me. You don't know who I am because I live in New Jersey. But it's important for me to be unanimous." I decided to let the New Jersey and "unanimous" slide.

"I have a solution. I'll take a sleeping pill right before your visit. That way I'll be able to truly live out my fantasy and you won't have to worry about my waking up and seeing you."

Kyle responded with a long string of thumbs up and smiley emojis.

"Alright then, Kyle. I'll let you know when and where."

---

"Sam, thanks for suggesting this trip. It's been so long since we've been to the city." Grace and I were driving to a large cultural center about seventy miles from where we lived. We were planning on going to an art museum there. We were listening to a podcast about recent human archeological discoveries in the Middle East as I drove.

"The timing is perfect," Grace continued. "And it's excellent that you were able to book that same Airbnb condo that we stayed in four years ago. It's so nicely laid out and such a good location. We can easily walk to the museum from there."

"And it's set up perfectly for my plan," I thought. "Sadie" had messaged "Kyle" about the city and time frame, and indicated she would message him the exact address shortly before the planned rendezvous.

We spent the afternoon browsing through several galleries at the museum. As the museum was large, we decided to devote most of our time to an extensive temporary compilation of works by Edward Hopper and then spent the remaining time viewing the museum's permanent collection of German Expressionist paintings.

As we walked through the galleries, I spent an equivalent amount of time admiring Grace's figure, which was provocatively displayed in her long white form-fitting dress. I enjoyed the subtle way her nipples elevated her dress, and it was easy to make out the contours of the aesthetically pleasing ass.

After we made our way back to the condo early that evening I offered to make drinks for the two of us.

"Yes, let's have that bottle of merlot you brought. I'll be back in a minute. I have a surprise for you, Sam."

Grace disappeared into the bedroom while I poured us each a glass of wine, carefully adding the powered Halcion to my wife's drink. Grace reentered the room wearing her green teddy. "Do you remember? I wore this last time we were here. I know you liked it."

I did indeed remember. Visions of Grace in the teddy, her legs splayed wide in view from the street through the open blinds, the voyeur lingering to memorize the intimate details of my wife, the cucumber slowly entering and exiting my wife all went through my mind instantaneously.

I smiled at my wife, feeling as though I had been transported back in time. Her nipples lifted the sheer translucent material. Her grooved vulva formed the top side of the Toblerone triangle between her legs. I felt my penis start to rise.

"I wish you knew how much of a turn on you are," I said to her.

"I know it's early but maybe we should just go to bed now," she said.

"Let's sit over by the table and have a glass of wine first."

As we sat at the table sipping from our wine glasses, I was easily aware of Grace's desire. Her blond/light brown hair framed her beautifully symmetric facial features. Her blue/grey eyes open wide in an inquiring expression. I could see that she was breathing rapidly as she looked at me.

Seeing that she had finished her wine, I stood up and walked behind my wife, reaching around her to gently clasp her breasts. I flattened my palms and used a slow circular motion with my hands, touching her lightly to stimulate her nipples. Her nipples hardened and rose in response. I could hear her breathing become more ragged with lust.

I reached down between her legs, placed my middle finger at the slit. It slid into her without resistance, fluid copious at both the portal and inside.

"Sam, y..you never g..gave me a firm answer about having another baby," she stammered, her mind occupied with the sensations she was feeling. "If you're w..willing this would definitely b..be the right time." I had increased the pace of the digital stimulation and loud wet smacking sounds emanated from between my wife's legs as she spoke.

I led my wife to the bedroom and pushed her back on the bed. She looked up questioningly at me. I put her knees over my shoulders to spread her legs then dropped down and directly and firmly placed my mouth over her clit and rapidly flicked my tongue over the small knob.

"Aggh. Oh my, god!" she squealed. It sounded as though she wanted me to stop but this was belied by the fact that she had placed her hands behind my head, pulling my mouth more firmly against her clit. "Oh, Oh, Oh, my god," she gasped in synch with the movement of my tongue across her clitoris.

After several minutes, I used my lips to gently grasp and sucking Grace's clit so that it was fully emerged, she began to move her hips in concert. With my hands wrapped around her spread legs, I could feel her quadriceps contracting and releasing.

After several minutes, I could tell my wife was building to climax. "Ah, Ah, Ah, Aggh!" she uttered repeatedly as she pulled my face into her with even more force. As she slowly came down she eventually released her hands from the back of my head. Now my wife was soaking wet from her fluid mixed with my saliva.

"T..thank you. That was so good," she said quietly. "Let me lie here for a minute. I'm exhausted. I wasn't sure I going to be able to stop coming."

After a time I rose from the bed. Grace was fast asleep. Opening Signal on my phone, I typed in the address of the condo for Kyle along with the message. "I'll be in bed and asleep when you get here. Please remember to respect my fantasy. Oh, something I didn't mention, I'd like it if you would talk dirty to me when you're here. I don't expect to be fully awake but that turns me on.

I received and immediate response. "Okay. I see the place on the map on my phone. I'll be over soon. Yes, I know your fantasy."

I went back to my wife and used a washcloth and towel to dry the outside of her vulva and mons, both still wet from my saliva and her fluid. I turned on the floor lamp near the bed as well as a small lamp on one of the night tables. I rolled Grace over so that she was face down with her right leg bent at the knee and pulled up toward the side of her body. Pulling the teddy halfway up her back, her toned ass was lifted slightly, her outer labial lips parted, revealing an enticing hint of the pink interior. She truly did look as though she were presenting herself to be fucked.

Part of the reason that I chose the condo for the weekend was that there was lockable pocket door between the bathroom and bedroom. When locked, there was enough play in the door that it could be slightly opened, enough for clear view of the bed. I entered the bathroom, locked the door, turned off the light and waited.

---

A door open and shut quietly. Stealthy footsteps approached. Wilton entered tentatively, followed by his friend, Brad. I had expected just Wilton but should have anticipated that he might bring his friend along.

"Dude, I can't believe this," Brad whispered to his friend. "I was Sus all the way over. But here she is. High key, there's no way she knows it was you who was messaging her. She wouldn't have dared let a student see those pictures."

"It's weird to see Dr. Overton here," Wilton whispered back. "She's so hot. Look at her butt. I can't believe I'm seeing this."

"No cap, man. But she says this is her fantasy," Brad snickered.

"I spend most of the time in her class trying to picture her without her clothes on," Wilton continued. "Now..., she looks even better than I imagined.

"I'm a little weirded out though. What if she wakes up and sees us. I already might be failing. I'm in enough trouble as it is. If my dad finds out about this... I think maybe we should leave."

"Chill bro, she would be in more trouble than us. She's the one who wanted this. She invited us. Or she invited you at least. She's supposed to be out.

"After the way she threw shade you when you asked her for help, this is a chance for you to bring her down a couple notches. Why don't you go touch her and make sure she's really out."

Wilton stared indecisively at Grace then slowly walked over. He gently placed his hand on her right calf and shook it gently. "Dr. Overton?" he said in a low voice, then with a harder shake, "Dr. Overton?" in a louder voice.

"Hey bro, you better call her Sadie," Brad whispered. We know her real name but let's play her game. She also said you should talk dirty to her. "Brad went over to the bed and shook Grace's shoulder. "Hey Sadie, are you ready to take some cock?"

Wilton slowly slid his hand along my wife's leg. "Her skin is so smooth," he said. Look at her legs. He slowly ran both of his hands over my wife's thigh then tentatively ran his hands up and over across the toned globes of her ass. Suddenly, he backed away.

"What's wrong bro?" Brad asked.

"I..I almost.." Wilton stammered. I could see Wilton's penis elevating the grey sweatpants he was wearing.

"Bruh!" Brad laughed. "You almost came in your pants?"

"Well, this feels like...I'm dreaming. Look at her butt. and um.. I'm not..."

"Hey man, are you aren't a virgin, are you? Well, you've at least gotten to third base with a girl before, right?" Brad asked.

Wilton was blushing. "Well, no, I've had sex before. With two different girls. But Dr. Over..I mean Sadie is so different. Her body looks like, like a model. I.."

"Ha. You mean you think she's out of your league. Yeah, there are plenty of Boujee girls who try do that to us guys. You have to realize that they're not really any different underneath. She might be Extra but she's not out of your league. Her bare ass is just out there waiting for you. She's the one that set this up. She's the one that wants you to fuck her. She's the one who's vulnerable now."

Wilton took off his glasses, set them down on the night table and returned to my wife, again slowly running his hands along Grace's legs, finally returning to her ass, he spent several minutes touching my wife's ass and lower back, tracing his finger along my wife's butt crack. He grasped the two cheeks of Graces ass, pushed them apart and moved in closer. Grinning, he said, "Wow. I can see her..her hole."

"Try touching and rubbing her pussy," Brad suggested. "I see she left some lube for you in case she needs it." Grace had brought our KY from home and had set it on the bed table in case we wanted it for our planned love making session.

Wilton touched Grace's vulva. "She's all wet," he remarked, surprised.

"Yeah man. She likes what you're doing. She won't need the lube. Try putting a finger in there."

"Oh, she's so warm and wet. I..I like the way this feels." Wilton cautiously explored Grace by inserting and extracting a finger, then inserted two thick fingers he started to more rapidly finger fuck my wife. Lewd smacking sounds reverberated around the room. He had a wide grin on his face.

"I bet you wouldn't have been so mean to me if you knew that I'd have my fingers inside of you. The sides of your pussy are squeezing my fingers.

"Do you think that's too much to say?" Wilton whispered to his friend. "She wanted me to talk dirty to her."

"No man, that's nothing. That's barely talking dirty. Anyway, you're doing what she wants. Hey, let's roll her over and have a look at her front," Brad suggested.

Brad came over and quickly rolled Grace over. "M..Max?" Grace exclaimed. Both of Grace's students stepped back and froze.

After a few moments Brad said, "It's ok. She's just dreaming. On her message she said she'd be mostly out. "Wow, look at her tits. Those are amazing." Brad took a phone out of his pocket and took a picture of my wife.

"I've spent so many hours imagining what her boobs look like," Wilton said. "You can see the shape through her clothes but, wow, they're beautiful. Look at how her nipples are sticking out. They're so nice and light tan and also the round part around the nipple."

Wilton leaned over my wife pulled Grace's teddy above her breasts and sucked one of the nipples into his mouth. He held it in his mouth then released it and used his tongue to trace the circumference. Grace's nipple rose, straining toward the ceiling. "I love your tits. Now I know what they look and taste like. I won't have to use my imagination when you're walking around in front of the room giving a boring lecture." Wilton took Grace's other nipple in his mouth stimulating it to match the first.

"I wish I could make your nipples stick out like this any time I wanted.

"Brad, look how nice her..crotch looks." Her lissome body extended along the bed, legs slightly apart, Grace was unbearably enticing. Her hip bones projected just above her flat tummy, her neatly trimmed pubic hair tapered downward to her raised mons. The tip of her clit had emerged from the digital stimulus she had received from Wilton.

"Hey, man, it's time for you to do the deed. You're going to have to lose the clothes."

Wilton slowly stood up. He took off his shirt, exposing his corpulent belly, and fatty breasts overlaying his pectoral muscles. He then dropped his sweatpants on the floor and took off a pair of dark blue Calvin Klein underwear. Wilton had a chubby, extremely pasty white ass, but when he turned I was surprised by what I saw. Already fully erect, Wilton's uncut penis was not especially long but it was of remarkable circumference. The head of his pale white penis projected beyond the foreskin and was visibly wet with precum. Though the head was of average size, the shaft tapered outward and was substantially wider and fatter than the tip. "It looks like a white cucumber," I thought to myself, recalling that Grace had received an actual cucumber in this same room the last time we stayed here.

Wilton bent to the pocket of his sweatpants on the floor and pulled something out. "I better use this," he said to Brad, opening a square condom wrapper. "I want to be safe. Also, I don't want her to accidentally get her pregnant."

"I think she wanted you to do her bareback. In her message she said she wanted to know she had a stranger's semen inside her. At least that's what it sounded like. She must be on birth control. There's no way she would risk getting pregnant."

"I've never actually done it without a rubber," Wilton said. "That's supposed to be the safe way."

"Bro, it's your call."

Wilton hesitated, then tossed the condom on the floor and went to the bed. Placing his arms behind Grace's knees he spread her legs wide, kneeling between them. "I can't believe I'm actually going to fuck Dr. Over..," Wilton said to his friend. "I can't believe in my wildest dreams I'd ever have the chance to fuck someone like...like, someone so pretty." The head of Wilton's penis had entered my wife.

Wilton lingered without moving then started gently thrusting into Grace, first gradually inserting his cock into my wife just an inch or two. I could see my wife's vulva stretching wide to accommodate the thick middle of his penis Then Wilton pushed forward fully entering my wife.

"Oh, wha..oh," Grace murmured. M..Max? Are..you?"

I expected Wilton to stop and panic but he and already started thrusting. He clearly was beyond stopping at this point. The bed started squeaking in rhythm with Wilton's thrusts and his weight. Grace settled into a hypnotic repetitive, "Ah, ah, ah, ah, accompanying each thrust.

From my viewpoint through the crack in the bathroom door I could see the two intertwined joined bodies. My wife lay underneath Wilton's mass. The legs of her slender athletic body split wide, knees hiked back to accommodate Wilton. The fat on Wilton's ass shook with each thrust.