Jen takes a strap-on

“Well, looks like you lost,” Monica said, still laying on her back. She tilted her head toward Jen. “I have to admit, you gave me a good workout! You got this far, after all!” She looked at her chest and squeezed her boobs together to emphasize her point. Then, she let them flop back down against her chest and chuckled.

Jen sat up as her eyes lingered on her opponent’s female anatomy. If anything, she had earned the right to look at them, after managing to take Monica’s top off. It was a small victory in a hopeless matchup. She gazed in reverence at the plush globes and Monica smirked, sitting up as well.

“There was no way you were supposed to get any points on me! I can’t believe I let you score! It makes me feel like I actually lost a bit,” the former pro mused. Then, she narrowed her eyes and grinned, adding, “But not badly enough to give up my prize!”

Jennifer stiffened up and took a dry swallow, but said nothing.

“You asked for this, remember?” Monica noted. “I don’t want to leave you with the false impression that you can just challenge a vet and think you can get away with it unscathed!”

Jen ducked her head sheepishly. “I’m sorry,” she said.

“Oh no, you’re not getting off with just an apology!” Monica grinned devilishly. Jen could already feel her heartbeat quicken as the tall brunette got to her feet.

“On your knees,” she ordered in a disciplinary, yet cool tone. Jen, as the loser, had to do whatever the winner said. She kneeled and straightened up. “Eyes front,” Monica commanded next. It was more like she was giving gym instructions instead of orders. Jen followed the instructions and faced the wall where the clock was. “Stay there.”

The former pro walked around her fledgling student and dug into her gym bag. Jen wanted to turn around to see what she was getting, but did not want to risk getting caught. She stared straight ahead and waited, feeling a shiver from both the cool air hitting her sweat and oil coated skin, and the uneasy excitement of what was to come.

Jen nearly jumped when she felt Monica’s hand on her shoulder. She gasped as she felt the warmth of the hand brush her along her neck, then down her back. It pushed her forward and she leaned in with it. Monica positioned her on all fours without a word.

The nubile young woman felt her mentor’s warm hands run up and down her body. They were fleeting touches, almost teases. This was nothing like the firm fingers pressing into her flesh from the massage earlier, nor was it like the controlled locks and holds of their match. These touches were bringing out a lust in her in the most graceful of manner. She felt the fingers tickle her underside, grazing along her fully erect nipples, then they reached behind to caress her soft round ass. Her breathing started to get ragged. She wanted to beg for more, have those fingers shoved deep in her pussy, but Monica was dictating the pace.

Finally, all the build up led to Monica slipping her fingers between Jennifer’s ass cheeks and reaching under, cupping Jen’s swollen pussy. Jen shivered and moaned. Her knees started to quiver as she felt those fingers press deeper and deeper into her hole. “Ahh….” she let out, involuntarily. It was like the steam was finally let out of a pressure cooker.

“Mmm…” Monica moaned softly as the masseuse worked her fingers inside Jen vaginal walls. “I’ve been wanting to do that since the moment I saw you!”

Jen felt her cheeks redden from the realization that.Monica had her eye on her from the start! In all the times she had been naked in front of the massage therapist, Monica was eyeing her like a succulent piece of lady meat. Jen was now feeling doubly exposed! Her pussy tingled with excitement and her body ached for more.

Monica removed her hand from Jen’s pussy. Jen started to turn to see what was going on, but was cut off by Monica’s command. “Eyes front!”

Jennifer straightened up, staring straight, feeling like she was a dog or pony, posed on all fours. She felt Monica caressing her again. There was more pressure behind the strokes now. Her hand grasped Jen’s butt cheek and squeezed. Jen yelped!

“Mmm….” Monica giggled. “I like the sound of that! I’m going to have to make you do that even more!”

Jennifer bit her lower lip. She got the feeling she was going to be taken full advantage of! As frightened as she was, she kept telling herself that she had asked for this. She was going to take whatever Monica was going to dish out!

Monica positioned herself directly behind her prize. Jen felt one hand on each cheek. A sharp smack on her right cheek caused her to yelp again! Monica giggled and rubbed the mark she left there. Jen squirmed uneasily and felt another sharp smack!

“Stay still!” Monica reminded her.

“Yes, ma’am…” Jen replied.

“Good girl!” Monica praised, placing one hand on each cheek again.

Jennifer felt her butt cheeks spread and started to panic. She had no idea what Monica was planning and it both scared and aroused her. She felt something press up against her from below. It pushed against her from one point. She gasped. It found its way along the young woman’s slit and she felt it push against her opening!.

“Ahhh!” she gasped, trying her best not to wriggle around.

The object pushed in further. Jen’s face was in shock as she realized Monica had brought along a strap-on dildo!

“AaaaAAhh!” Jen groaned, feeling the length of the sex toy fill her from inside. She wanted to writhe and squirm, squeeze her legs together and touch herself, but she obeyed her mistress’ command and remained still.

“Hmm… you’re so tight…” Monica noticed, reaching around and rubbing Jen’s clit from below. Jennifer closed her eyes and let out another moan. Suddenly Monica gasped. “Don’t tell me this is your first time!”

“N… no…” Jennifer managed to squeak out over the sensory overloading feel of her pussy jammed full of rubber cock. She did have the official WSW winner’s strap-on stored in her closet, and even tried it out before.

Monica wasn’t quite convinced though. “So… exactly how many times have you had a cock up your pussy?”

“Um…” Jen squirmed. “Once… by myself…” she admitted in a meek voice.

Monica covered her face and laughed. She knew this young woman was green, but didn’t realize just how inexperienced she really was. This didn’t mean that she was going to go easy on her though. This was a lesson on what Jennifer was getting herself into. The WSW vet leaned in and murmured into Jen’s ear, “Sweetie, you’re about to experience something life changing!”

Jen’s eyes widened as the weight of the woman’s words began to sink in.