The Gray Man Ch. 36 - Olivia

"Fuck, oh fuck, I'm going to cum... oh hell, what is happening..." the panicked intel analyst tried to push TJ away but he was far too big, far too strong, and far too stubborn. Gray's tongue just kept flying over her clit until Rebecca arched her back and locked her legs around TJ's head and a full blown orgasm like she had never felt attacked her body, causing her pussy to contract so hard she squirted. Her ejaculate covered Gray's face, mouth, and shirt.

When she had calmed down TJ looked up at her. Seeing his face she started to apologize, "Oh God, I'm so sorry. I'll get a towel, I'm so sorry."

TJ chuckled, "You're fine."

Rebecca shook her head, "There is no way that's normal! I'm a fucking freak."

Gray shook his head as he stood, "Calm down, you aren't a freak. Not every woman squirts, not every woman can cum from nipple play. It's not a freak thing, you aren't alone. Now, relax."

Rebecca reached out and wrapped her fingers around as much of TJ's cock as she could. "Easy for you to say, you aren't about to get impaled by a flag pole."

TJ smiled, "I'll be gentle. Now relax and place the tip at the opening."

Rebecca sighed and rubbed the mushroom head up and down her drenched pussy and placed the head at her opening. She looked down and saw how her lips had stretched to accommodate him. "Jesus, I'll be stretched out forever."

Gray pushed a bit so that the ridge slipped in, "No you won't. More lies, probably told you by a needle dick." Rebecca tensed up at his words, "Relax,"

Gray began to slowly push into her. Stopping every half inch or so to let her relax and adjust to the huge intruder. She would beg him, "Stop, stop, stop," and he would stop until after a few seconds she would exhale, "Okay, I'm ready. Give me some more."

Slowly but surely more and more of TJs cock slid into the petite Rebecca. Slowly, gently, but persistently Gray's cock snaked into her. TJ watched as a fine sheen of sweat started to cover her body. She looked up at her lover, "I can't. I can't.".. TJ smirked and lowered his mouth to one of her nipples and gently bit it between his teeth, knowing that it would start an orgasm.

Rebecca leaned back and arched her hips to push her tit further into Gray's mouth, while at the same time the contractions in her pussy allowed his cock to slide even deeper. Before she could recover from the first orgasm he moved his mouth to the other nipple which caused the same results. Each little spasm pulled TJ's cock deeper into her petite body.

"You're doing amazing Becca," Gray's voice almost sounded like a jungle cat's purr.

"How much more?" Rebecca panted.

TJ smirked, "3 more inches and you'll have all of it. Do you think you can do it?

Shyly Rebecca looked at him, "Can we move to the floor and let me on top? If you don't want to, I understand. Control for a man is important."

Again TJ shook his head, "Rebecca, controlling sex is only important to someone who has no natural power so they have to force it. Relax and wrap your arms around my neck."

Effortlessly Gray scooped up the petite vixen and slid to the floor, his cock embedded in her the entire time. He smiled at her and kissed her before he whispered, "This might be tricky, I want to lay back but I never want my cock to leave your body. Can you work with me on that?"

Years of dance and gymnastics came in handy as TJ tried to position himself. Flexibility was a good thing and Rebecca was able to adjust herself to her knees without every letting his cock completely leave.

Gray couldn't believe how soft, and warm, and wet, and tight Rebecca's vaginal cavity was. He had fucked a lot of women in the last couple of years, but never someone so petite. Her work bio read 4'11. 102 pounds. With the mental and emotional abuse she had taken over the years for her sexuality he vowed to himself to hold on as long as it took so Rebecca could enjoy herself as much as she needed.

Slowly, ever so slowly Rebecca lowered herself onto Gray's cock. She touched her stomach and could feel the cock behind her abdomen wall. "Jesus, so big." When Rebecca had lowered her hips far enough to consume the entire length of Gray's cock she sighed, "That's all of it."

TJ smiled, "Yes it is tiny one. You are amazing."

Rebecca raised her torso and placed her palms on Gray's pectoral muscles. She looked deep into his green eyes and began to slowly consume the man beneath her. As her rhythm increased Rebecca felt her insides heat up and she began to sweat. She dropped her head and looked between their bodies, and when she saw Gray's hard cock covered in her own juices as it slid in and out of her quivering body she moaned and whispered, "Oh Gah... look at it... its inside me... so fucking sexy... oh Gray... you're inside me. I think I'm going to cum I know you should cum first but I can't stop it."

TJ held her hips gently, "That's it, cum on my cock Becca, let it go. All of the lies, all of the abuse, let me have all of it." Gray held her hips so she didn't impale herself as her body quivered and quaked and her fists beat on his chest.

A growl that shocked her poured forth from her mouth as another powerful orgasm poured over her. The fragrance of Rebecca's long flowing hair entered Gray's nostrils, and as the soft strands brushed his face, "You smell amazing."

Gray felt the tip of his hard penis press several times against the back wall of Rebecca's vaginal cavity and even push deeper into her. He became so consumed by Rebecca's seductive motion he lifted his hips off the floor offering Rebecca more of his manliness.

When Rebecca felt Gray respond to her, she began rocking her hips wildly. Soon she was rocking her entire body to an ancient rhythm, only a woman consumed by lust would understand. In a few short moments, Rebecca's entire body was on fire and quivering out of control. Her breathing became more rapid and she lost all sense of direction. Suddenly she felt an incredible flash of electricity flush her body and her muscles stiffened as her inner muscles quivered.

Gray looked up but couldn't see Rebecca's face because her hair was blocking his view. He sensed she was experiencing a soul wrenching orgasm but he wasn't sure until he felt her inner muscles quiver against the skin of his stiff penis. Then she moaned very softly, dropped her body on Gray's body and began jerking slightly as Gray held on to her bottom. In a few moments Rebecca raised her head and pulled her hair to one side. When she saw Gray's face she lowered her head, kissed Gray gently on his lips then collapsed on his body.

Gray slowly lowered his hips as he felt the tiny woman's body rise and fall until her breathing returned to normal. Gray realized he was holding an incredibly beautiful woman with a surreal appetite for sex. Little did he know he had just witnessed Rebecca releasing something deep inside her soul. What they were doing was not fucking, nor was it love making, this act was healing for a broken and scared woman.

"Gray?" asked Becca softly.

"Yes," responded Gray as he smoothed the cool skin of her tiny round buttocks then her lower back then shoulders.

"Did you cum?" asked Becca in a soft voice.

"Not yet," responded Gray as he inhaled the fragrance of their sex.

Becca wiggled a little then lay very still as she felt Gray's heart beat. She wondered what she was doing wrong. She could always get her ex to cum, if not she would have been punished. Most of the time he would cum as soon as he entered her.

Rebecca had to know what she had done wrong so she asked, her head laying on her boss's chest. "What did I do wrong?"

TJ smoothed his hands down her feeling the coolness of her soft skin until his hand cupped the cool skin of her bubble butt. He gently squeezed her ass and whispered in her ear, "You've done nothing wrong. It just takes me a while."

Becca sighed as a peaceful glow filled her. She lifted her head and kissed Gray once very softly on the lips. Then she looked deep into his green eyes and simply stared into his soul. Gray stared back into Becca's big brown eyes and realized she was studying him in a new way. TJ was used to being the one who could look into another's soul, the fact that he knew exactly what she was doing was a bit disconcerting. "What?" asked Gray in a whisper, and then he added, "It's true."

Becca sighed, "I want to give you as much as you've given me. It's who I am. Take what you need from me. Please." Becca fell forward against his body and held on as Gray moved his heels under him and began to rock his hips. As Becca surrendered to her lover she felt a strong urge to let her body be used for Gray's pleasure. She had always been told there was something wrong with her, sex was always a weapon used against her. Today though, she felt something different.

After a few minutes of rhythmic balanced motion, Becca suddenly felt a strong tingle in her loins. She knew what was happening to her body and she let it happen. Becca closed her eyes and let Gray take complete control of her. It was something she had always been terrified about because she had been told it was too intense.

She knew she would reach orgasm in Gray's arms then it happened. Becca felt complete numbness then warmth filled her. She almost lost her grip on Gray's neck as she felt her inside muscles twitch.

Becca lowered her head then pushed her hips forward as the electric feeling consumed her body, "I'm going to cum again. I'm going to cum again before you. I'm soorr...," the apology never finished as her words dropped into a soul searing moan as her inner muscles twitched out of control and her arms tightened around Gray's neck.

She had held her breath waiting for the scolding words or for Gray to harshly spank her ass for disobedience. It never happened. Finally, she released the air in her lungs and let her body collapse. As Gray felt Becca' surrender and her inner muscles vibrate against his cock he began to cum. Neither of them moved, they laid together, her walls twitching and his cock exploding. The feeling of Gray's penis twitching inside her again set Becca's body into another world and she lost all control. She felt the emotions pour out of her.

Rebecca could not believe that she was crying as her body was in the midst of a mind blowing orgasm. When her petite body finally stopped shaking she again whispered, "You must think I'm a fool."

TJ moved his hand to turn her chin. "Actually, you just reminded me of how amazing sex can be when you involve more than just your body. Kiss me, Becca."

She kissed him, this time her tongue moved into his mouth as the salt of her tears mingled with the taste of her own pussy that he had so amazingly eaten just minutes earlier.

Rebecca thought that if this were anyplace other than the floor of his office that she could sleep like this, Gray's semi hard cock still inside of her, her head resting on his chest. She felt more free than she had felt since college. Somehow in his own unique way, TJ Gray had slain the dragon that had kept her captive for most of her life. She felt seen for who she is and more importantly accepted for who she is.

The next few days around the office were a bit chaotic as Gretchen felt that construction had fallen behind schedule while Allen and Valerie, freed from the dark shadow of blackmail, returned to get more involved in the day to day building process. On top of that Admiral Barnett was on leave, enjoying some time sailing in the Caribbean.

Gray found himself finding more reasons to be out of the office. His absence was being noticed as well. A week or so after the encounter with Rebecca, TJ had walked out of a meeting at SynergyTech, changed into running clothes and took off for a long run, enjoying the warm late April sunshine. As his run was ending Gretchen sent him a text about meeting for lunch.

TJ replied that a late lunch would work because he needed to shower and change after the 5 mile run. The two agreed to meet at 1300. A quick shower, change of clothes, and a short drive allowed Gray to pull into the parking lot as his watch chimed the hour.

When Gray entered he saw Gretchen seated at a cozy corner table in Potomac Grocery. The hum of conversations and the aromatic blend of various dishes filled the air as they settled in. TJ was thankful that most of the lunch crowd was already headed out the door and back to work.

Gretchen couldn't help but express her curiosity about TJ's recent absence from the office. Leaning forward slightly, she raised an eyebrow and asked, "Teej, What's going on? You've disappeared a lot lately. The office feels a bit emptier without you. Everything okay?"

TJ took a sip of his beer, contemplating how much to reveal. He knew Gretchen was perceptive, but he also didn't want to dive into the intricacies of the tension between her and Allen. "Gretch, I'm a field agent - being inside too long makes me a bit stir crazy and to be honest the bickering between you and Allen is a bit much at the moment."

Gretchen nodded knowingly, acknowledging the challenges she faced with Allen. "I get it, TJ. Office politics suck. In truth though, Allen and I are just a couple of powerful personalities who are both used to getting our way. At the moment we just have a bit of a disagreement in priorities for the construction. I'll work on being a bit less bitchy about it. Fair?"

TJ nodded, "Fair. Remember, I'm just an old Army grunt. These conversations dealing with tens of millions of dollars is just not in my wheelhouse."

Gretchen winked at her cousin, "Stop underestimating yourself. It doesn't look good on you."

Their orders arrived, diverting the conversation momentarily. TJ's Hot Pastrami Sandwich was a tempting tower of deli goodness, while Gretchen's Caesar Salad with Shrimp looked fresh and inviting. As they dug into their meals, the atmosphere lightened.

As the lunch progressed and the clinking of cutlery echoed around them, Gretchen broached a subject that weighed on her mind. "So, Teej, you want to get out of the office and we aren't quite ready for full blown clients yet, so maybe we can find a win/win. I've got a favor to ask," she said, choosing her words carefully.

TJ noticed the ornery glint in Gretchen's eye, "I've seen that look before, you've definitely piqued my curiosity. What do ya need?

Gretchen hesitated for a moment before unveiling the heartfelt plea that lingered beneath her composed exterior. "Olivia Harrington, my friend from New York, needs someone by her side. She's been through a rough patch, caught her husband in an affair, and now she has to face him and his new girlfriend at a black-tie gala. Olivia is the Chief Investment Strategist for Tower Capital, she is on the board for the charity and..."

TJ's brows furrowed, "Gretch, what did we agree to before, I'm not an escort service."

Gretchen put up her hand, "You didn't let me finish. First, she didn't ask for me to find her someone, she was just bemoaning the reality. She also mentioned she hadn't had sex in a year and she doesn't trust anyone. She manages a multi billion dollar portfolio, the men that show interest show more interest in her checkbook than her heart."

Gray leaned back, "That doesn't change the fact that you want me to be arm candy."

Gretchen sighed and pulled up her phone and showed TJ a picture, "Teej, she's beautiful and kind. She was a client of mine when I first got out of law school. She's about ten years older than us. C'mon, be a sport."

TJ shook his head, "Gretchen..."

His cousin smiled, "What if she wants a date that she can trust, a date that won't take no for an answer when it comes to after the party?"

Gray rolled his neck and shoulders, "Is that what she wants?"

Gretchen's fingers flew over her phone as she was sending a message. "I don't know, I'll let you know."

TJ leaned in, his voice low and threatening, "What the fuck did you send her Gretch? That was more than typing."

Gretchen laughed as she turned her phone around, "Oh, just this."

TJ shook his head when he saw a text asking Olivia if a date that agreed to not take no for an answer would work for her. Included were a picture of Gray in his running shorts, his bulge clearly visible and one of his face. He shook his head, "Jesus, and you call me incorrigible."

Gretchen chuckled as she sipped her wine and waited. A little over two minutes later her phone buzzed. When she looked at it she smiled before she read the reply, "Holy hell, where did you find him?" Her fingers composed her reply as she spoke softly, "My cousin, trust me. He will have Nicholas rethinking his world. He's taller than Nicholas, has a presence that every eye in the room will notice and as you can see is hung like a horse. If you want the total package for a night just say the word. Putting Nicholas in his place, making you look amazing, and fucking your brains out no matter how much you protest, just say the word."

Gray folded his arm, "Are all women like this? Good Lord."

30 seconds later Gretchen looked at her phone and turned the screen to show her cousin, "God, I love you! Yes, Yes, Yes! I'll have my assistant get him a suite at The Casablanca right across the hall from me. Give him this number and I'll send him all of the details."

Gray and Olivia texted a bit back and forth leading up to the event on Friday night. He took the train from DC to New York on Thursday night, checked into The Casblanca, ordered room service and enjoyed the amazing view of the World's financial center. He shook his head at the irony that he was knee deep in finance on his mission to Shanghai and found himself once again surrounded by folks who could buy every single thing he owned and not even notice the transaction in their bank account.

Olivia took Friday off to prepare for the evening. In the soft glow of the city lights filtering through the expansive windows of her suite, Olivia stood before the mirror. The room, adorned with tasteful decor, echoed the sophistication befitting a woman of her stature. Yet, on this particular evening, the ambiance couldn't dispel the fluttering nerves that danced within her.

Draped in an elegant gown that cascaded like liquid midnight, Olivia ran her fingers lightly over the fabric, a sigh escaping her lips. The dress, chosen meticulously for its subtle allure, clung to her curves in a way that whispered of both power and vulnerability. She studied her reflection, her hazel eyes reflecting a mix of excitement and trepidation.

"Is this too much?" she murmured, her voice a melodic cadence that resonated with the confidence she projected daily in the boardrooms of Tower Capital.

Her fingers traced the delicate necklace that adorned her neck, a symbol of understated opulence. Yet, despite the external display of regality, doubts lingered. The weight of societal expectations, even for a woman of forty-eight, bore down on her shoulders. A whispered lament escaped her, "Why should I care so much about what he thinks?"

As she delicately adjusted the straps of her heels, frustration crept into the corners of her mind. She, who navigated the complexities of the financial world with unwavering poise, found herself entangled in the web of sartorial uncertainty and, dare she admit it, a touch of nervous anticipation.

A knock on the door interrupted her contemplation. "Ms. Harrington, your car is ready for the gala," the hotel staff announced, their tone respectful yet punctual.

Olivia took one last lingering look at herself in the mirror, summoning the strength that had propelled her to the pinnacle of her profession. "You've got this," she whispered, a mantra to drown out the self-doubt.

As she stepped into the dimly lit corridor of the hotel, the scent of her chosen perfume lingered in her wake, leaving an invisible trail of allure. Clutching a small handbag in front of her Olivia stepped from the elevator,the soft rustle of her gown seemed to harmonize with the anticipation humming in the air.