Joy was Andy’s girlfriend, before she met him, she was just a girl in poly, doing her best to get good grades. Hardly distracted by issues of sex, she was focused and happy-go-lucky. Then, after the CCA open house, she knew Andy, and quickly gave into her naive and simple perception of love. Dinner dates, movies, holding hands, kissing, making out.. those were parts and parcels of a relationship and her innocent mind had no guard against such advancement. However, the progress stopped when Andy wanted to lay more than his fingers on her pussy.
She knew there were considerations, and of course, preparedness too. Weeks gone by since he asked for it, but Andy was not pushy about it. And that was probably the last time he spoke of it as well. Sex was considered part of love, and the space he gave was reassuring. So, for their anniversary, Joy agreed to spend the night with Andy in MBS as part of the plan.
Night came and things got a little heated up after the bottle of wine. She was in her white translucent night gown and he was naked before her. Andy took out a blindfold and placed it over her eyes, Joy complied. She knew something would be coming, and sex would be on his list. Her eyes remained closed despite having the cover over her eyes. His hands laid on her ankle and glided sensually up to her thighs, lightly spreading them apart. His hair then tickled her belly button before she felt his soft tongue on her clit, licking warmly, wetting the sensitive spot.
Joy resisted the reaction to shut her legs and sighed, while grabbing the sheets under her hands. Her body got even warmer and her nipples grew pointed. Andy pulled away after a few minutes of high-speed flicking and sucking, seeming to be preparing something in the distance.
Andy: ‘Just relax k?’
He pushed his fingers along the wet lips of her pussy and it swiftly went in, all the way to her deepest point. By then, she was ready to give him her virginity, if he went on. His fingers quickly picked up speed and was going in and out of her, overwhelming the initial wetness of saliva. Her pussy had been squirting out little waves of juices, onto his fingers and the bed. Her body was totally relaxed and ready.
Andy reached out to the side and took a syringe, filled with a whitish liquid. He placed the opening at her ass and forced all the liquid into her, volume manageable to her. Joy was surprised, but did not respond immediately as she thought it could be her stomach. Then, as Andy served up another glass of wine through her lips, and she felt her bottom loosen.
Joy: ‘Andy, I need to go to the toilet.’
She pulled off the blindfold and went to the see-through bathroom, and covered her face as the splashes resonated loudly while brown chunks were dumped. It merely took five minutes for her body to empty her bowels and bladder, but the energy left in her was barely usable. Andy went in after she flushed and he picked her up and placed her on the bed.
Andy: ‘I think you are really relaxed now.’
He placed a spare pillow between her legs and turned her to the side, like how you would sleep sideways. He had coated his dick in a generous amount of KY and on his pinky, a big blob of petroleum jelly. He placed the blindfold back on Joy and she hugged the pillow even tighter as his pinky came in contact with her anus.
Joy: ‘Is it going in there?’
Andy: ‘Yes. Just relax.’
He waited a few seconds before the hole loosened and his pinky poked in. With the aid of the jelly, her natural reflex to squeeze and ‘push’ was negated, totally useless to his invading finger. The full length penetrated her ass and Andy was busy getting her to relax so the bigger stick could enter. He pulled out after fingering her ass and switched to his bigger weapon. As he pushed his head in, Joy was busy trying to breath in rhythm, like a woman in labour. Her ass had been cooperative and Andy had just passed the mushroom mark. What was left was his shaft, which was 4 inches.
Andy: ‘Joy, I love you. And tonight had been great. The music, the view.. ‘
His voice calmed her while he continued to make his way, claiming her anal virginity. After it reached the halfway point, Andy gave a sigh of relief and decided it was enough. He applied more KY and began to pull out, leaving the vacuum in Joy.
Joy: ‘No no! Wait. Don’t pull out! We’ve come halfway, might as well.. ‘
Andy: ‘Nope. We cannot do it this way.’
He pulled out at a speed Joy panicked that there would be some faecal left, but his dick was perfectly clean. Just as he was about to pop out of her, Andy grinned and rammed his shaft all the way in, making Joy scream and grab the sheets wildly. As she was still facing the side, Andy held her shoulder in a lock down and her knees together. With all the support in place, he began thrusting his dick in and out of her ass, while listening to his girlfriend plead for mercy.
Joy: ‘Please stop. I’ll have sex with you. Please take it out!’
The pain was slowly going away, but it was the weirdness of anal sex that bothered her. The man did not stop and kissed her instead. Her tongue reached into his mouth and frenched wildly in an attempt to reduce the awkwardness. Her mind had debated in the rightfulness of anal sex and Andy won. The KY Jelly had worked great and after a frantic five minutes struggle, Joy was moaning, with her hands between her legs, fingers rubbing on her clit. She found her way to relax.
Andy on the other hand, had been enjoying the tightness and her willingness to let him own her butt. As the night was still young, he decided to finish the first round so he could rest with her. Going smoothly in and out of her, Joy’s expression was priceless and Andy got more turned on by her openness.
Minutes later, Andy groaned and Joy opened her eyes, in front of her, the young man’s face changed to an orgasmic one and she had to agree it was wonderful to feel his love get pumped into her rectum, deep and hot. He felt onto the bed behind her and his shrivelled dick shrank out of her. Joy clamped her legs tighter and held all his cum in. She turned to him and gave him a peck as he drifted to sleep out of exhaustion.
Joy could not help, but slipped her fingers into her ass to feel how much cum he poured into her, and while digging, she discovered.. that having both her holes filled was better than just having one. Both her hands worked her out for another fifteen minutes, finger fucking her ass and massaging her pussy till she passed out from one of the intense orgasm she experienced that night.