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.
