The two did have pizza. A stroll thru the mall. A little shopping and finally a drive downtown to the Emmerson hotel. The valet opened the passenger door and then raced around to the driver side only to find Annie already out and handing him her keys.
"Guest room number?" He asked.
"Just dinner." Annie calmly said.
Jessie grinned when she heard Annie offer up such a blatant lie so easily.
Annie took the valet stub, came around the car and took Jessie's hand. The two strolled in the front doors as a number of onlookers admired the view. Once in the elevator, Jessie let out a breath she had been holding. Annie looked at her.
"Are you okay?" She asked.
Jessie nodded.
"If you're not, we can go home right now." Annie offered.
"No, really." Jessie said. "I'm only worried what dad would do if he found out." She said.
Annie hugged her. "Thinking about telling your father you had sex with a black man?"
"That's not even funny." Jessie said.
"Well, I'm certainly not." Annie said.
Annie ran her hand over Jessie's shoulders and down her back. "The only advice I can give you is to relax and let it happen. Enjoy the freedom you are claiming for yourself."
Jessie seemed to settle right down. As the elevator doors opened, Annie patted her little ass. She took Jessie's hand and as the two walked down the hall to room 1244, Annie gave Jessie one more bit of advice. She whispered it. "If you don't let it hurt just a little bit, sex can't bring you the pleasure you really want."
Annie knocked, the door opened and the two were greeted to Brad's genuine smile. He stood aside and the two entered. The room was impressive, the Emmerson being the nicest hotel in town.
Annie gave Brad a long sensuous kiss as Jessie watched,
"My friend, Jessie." Annie said. "Jessie, say hello to Brad, good friend of mine. Brad looked to Jessie but she just nodded. Annie retrieved a beer from the small fridge.
When she sat down on the end of the bed, she patted it and Brad sat beside her. "No reason for preliminaries, we all know why we are here. She held out a hand toward Jessie and Jessie moved over to stand in front of her. As she ran her hands up the sides of Jessie's legs, she said. "This one is very important to me." Annie looked to Brad. They had already had this conversation but Annie wanted to refresh it and she wanted Jessie to hear it. "She is fresh and vulnerable and I want her first time to be one that makes her want a second one.
Annie stood and pulled brad to his feet. She slid her hands under his tee and eased it up and over his head, letting it fall. Her fingers undid his belt and pulled his zipper down. She had to work to get the tight jeans over his hips. As she knelt in front of Brad, she looked at Jessie who seemed a bit mesmerized.
She slipped off his shoes and slid the pants free. Brad stood there in the tightest of briefs. Annie's practiced fingers worked them down as his nearly erect cock sprang forth. She heard Jessie muffle a gasp. She looked at Jessie who had brought a hand to her mouth.
She smiled at Jessie. "Being willing to vocalize yourself during sex is part of the pleasure."
"It's, he's, incredible." Jessie stammered.
Annie freed Brad from his last garment. She took Jessie's hand and pulled her between them, facing Brad. With her mouth so close to Jessie's ear, she whispered. "Feel him."
Timidly, Jessie wrapped her fingers around the biggest cock her amateur eyes had seen.
She felt Annie unzipped her dress and push it over her shoulders. She switched hands on Brad's cock once so the dress could be slid down over her hips and she stepped clear if it.
"Get on the bed." Annie whispered. Jessie didn't really want to turn loose of Brad but she knew Annie was in charge.
As Jessie lay there, watching the two of them, Annie turned Brad to the side and knelt in front of him. Her fingers went into her front pocket producing her elastic restrainer. She squeezed is balls together and stretched the band over them. She worked it up as high as she could, tight against his base and then she pulled on the loose end tightening it around his scrotum. Brad stood still. She pulled the adjustment again and Brad leaned forward yielding to her strength. She looked up at him. "Tight enough?"
Brad nodded. Annie slid her fingers back under him once more and finding the end, she pulled hard and Brad groaned and she felt his knees give slightly. She cupped his now captive testacies and then gave his ass a pat.
All of this had caused his cock the droop slightly. She looked to Jessie, still watching intently and then she lifted the beautiful member and let her lips slip over the tip. She began to suck that cock ever so skillfully and she felt his rod grow and stiffen in her mouth.
And again, her fingers produced an item from her pocket. Without looking or releasing his dick, she tore open the condom package. She let the cock drop from her mouth and placed the condom on its tip. Ever so skillfully, she brought her mouth back to him and rolled the rubber down his shaft using only lips and tongue.
She stood and turned Brad to the bed. "Slow." She kissed his neck. "Steady." She kissed again. "Nice long stroking."
As Brad climbed up on the end of the bed, Annie went and settled beside Jessie. "You ready for this?"
"Oh god." Jessie said. Well then, I guess we don't need those, she nodded at Jessie's panties. "I want you to take them off for Brad. Show him you are ready and that you want to be with him."
Without hesitation, Jessie pealed them off and dropped them on the floor beside the bed.
Annie produced a small tube, removed the cap and squeezed a liberal amount of lube onto her fingers. She slid her hand between Jessie's legs and smeared it along her labia and into her vaginal opening.
Annie went once more to Brad. "Give her a most fantastic fuck." She said. She cupped his nut sac again. "Is this strap tight enough? She fingered it, teasingly.
Brad put up a hand. "Trust me." He said.
Annie grinned at him. "I'll check it in a while." She offered. She leaned in, kissed him deeply. "Please don't hurt my baby."
She looked down at the two. Brad was already leaning forward. Jessie holding out her arms ready to wrap around him. Her knees slowly easing up. "I want to stay. To be here for you."
As Brad rubbed the head of his cock along her sex, Jessie gasped. "Please." She said through gritted teeth.
Annie didn't know if it was directed toward her or Brad. She took it as a yes.
Brad eased the head of his cock into her. Jessie started humming. Annie pealed her tee over her head. It was going to be a long evening, hopefully.
Brad was gentle. His mouth found Jessie's and his tongue searched out her own. He was easing his cock into her. In a bit, out to the tip and in, going just a little further each time but ever so slow. It was excruciating for him as everything he knew was telling him to fuck this girl. To get it in her. But Annie was special to him. He would do whatever she asked and right now, this was what she wanted.
As slow as he went, giving himself to Jessie, she was wanting it just as bad. She was mentally begging for him to shove into her. Like she now realized, Dave would never be able to do. It was then that the knob in Brad's dick rubbed along her vaginal walls pressing against her G-spot. She gasped as he began short strokes in and out against it.
Her slender legs jerked, her head rolled to the side. She thrust her hips upward so fast that Brad was unprepared for her. She alone took the remaining four inches of his cock all at once and she cried out as the head of Brad's dick pressed at her cervix.
She arched her back as her climax crushed her. "Oh my god." She said. Her ass was shaking. Her eyes glazed. She was running her hands up and down his back. "Fuck me, fuck me." She begged.
Brad, skilled as he was, continued to fuck her right through her orgasm making it last much longer. She se was finally beginning to settle, Brad pulled is cock out so far Jessie was certain he was finished with her. "No, no, no." She whined.
"Not to worry love." Brad whispered. "We have just begun." He eased back into her, steady deep fucking. Each time, as he was close to having his length in her, he would arch his back and his cock head would push right past her cervix and into her fornix.
It frightened her but it stimulated her to her core. She had never imagined something or someone could be so deep into her body. She shook every time he touched her farthest reaches. The next time he went there, pressing the head into her tight passage, his balls against her ass, his lips smothered hers and he began to rock into her. All of him, buried in her. He held her there, as she drew her knees up, forcing them apart. She pushed up to him, grunting now, gasping.
This was sex. This was fucking. She was with a man, not a boy. This was how she wanted to live, like Annie. She was fanaticizing as she came. Just like he was fucking her, slowly, it rolled through her body, making every hair stand up. Every nerve ending sent shockwaves to her brain. Her cunt was soaking the bed.
She didn't know when he stopped, when he pulled his cock from her. When her eyes opened, she was on her tummy. There were pillows under her middle. She felt Annie's hand first. It was rubbing the back of her neck, her shoulders.
Then she felt Brad. He was easing her legs apart. "A little more.' He urged. She tried to push them further out. She strained herself to do as she was asked. Brad was behind her. "Good, baby."
He rubbed the head of his cock along her labia. She was slick, her pussy welcoming. When his cock entered her this time, he slowly pushed completely into her.
She started. "Ugh, ugh, ugh, oh, yes." Her new position, with her ass in the air, gave Brad an angle where he could go even deeper into her. And he did so on his very first insertion, causing Jessie's head to bend back. Her mouth was open but her eyes were closed tight.
He reached up and gathered her hair in his right hand. He held her head back as he deep fucked her.
