Rosalind finally made it home and closed the door behind her holding a plastic shopping bag. Her girlfriend had recently managed to convince her to widen her horizons after being with each other for almost a year. Rosalind’s girlfriend was far kinkier than she was and had always wanted a chance to explore Rosalind’s second hole. Rosalind had been hesitant about this but she decided that she would try it as a valentines gift for her girlfriend.
She wanted to make sure she would be ready for her when the day came and following the advice of some online forums she went shopping for some new toys.
In the bag were her new goodies. She bought a few buttplugs ranging from a puny 1 inch diameter one to a far more impressive 3 inch plug. Also in the bag were some pink anal beads, the type with the ring at the end to grab onto, an enema kit and most importantly of all, a big bottle of lube.
It took a lot of courage to walk into the sex shop and buy it by herself but she knew had she asked her girlfriend to come with her she would have not only ruined the surprise but also received endless teasing from her for being so red in the face the entire time she was in the store.
Having just gotten back she placed the bag on her bed and went into the bathroom to take a shower and use the enema kit to make sure everything went smoothly.
Once Rosalind stepped out of the bathroom clean and ready for her first time. She layed out some clean towels on her large bed and layed down next to the bag.
Rosalind took a deep breath before sitting up and dumping the contents of the bag on her bed. She ripped the packaging off and tossed it on the floor before neatly laying out everything, from smallest to largest of course. She opened the bottle of lube and put on some quiet music to serve as background noise. Rosalind was ready and she said to herself quietly “here goes nothing” and squirted some lube onto the smallest plug.
She played around with different positions until deciding that laying face down ass up would let her insert it with minimal discomfort. The metal plug though small, was but still fairly hefty in weight. It had a pretty pink diamond design on the base that Rosalind really liked. She stood the plug up on the bed and rubbed some lube on her finger and then rubbed the finger on and around her ass. Rosalind decided she was ready and picked up the plug and as the forums said breathed slowly and deeply as she pushed the plug on her hole.
It took a few tries but on the third she managed to push the plug in. Rosalind let out a small moan and felt the cold metal plug weighing her asshole down. The process of getting the plug In didn’t hurt nearly as much as she thought it did and she was enjoying the sensation.
Rosalind got up and walked to her mirror where she turned around to admire her plugged ass. She was surprised by how comfortable it was and decided she would wear one for the little “valentines day surprise”.
She took the plug and moaned as it popped out and she noticed it was a little easier than putting it in but felt even better.
Next she lubed up the anal beads which were a little bigger than the plug. She felt nervous but figured that her girlfriend would want to put far bigger things in her eventually so she might as well get some practice in.
The first few went in fairly easily. The 3rd bead was about the same thickness as the plug and took a bit more lube and effort but she got it in. With every bead she grew more horny and more daring Rosalind got the next one in as well and was wondering to herself why she hadn’t tried this earlier.
By the 5th she had tried and tried but she couldn’t make it fit. Rosalind decided she would try one last time and using her slippery fingers she pushed and pushed until it went through painfully.
Rosalind collapsed onto her bed and rolling around she said, “fuck that hurt” but as the words came out of her mouth the pain started to fade and it was replaced by pleasure she reached down and played with her stiff clit and feeling more daring than ever when she had a thought.
She stopped and thought about it and in her head she wondered, “how bad could it be?” And she decided to go for it. She would film it so she could relive it later but also to show her girlfriend on that fateful night.
She got up and propped her phone up against a pile of clothes in her closet. She started recording and made sure everything was in frame. Rosalind got on her bed and crawled to the edge of her bedframe where she grabbed onto her bedpost and turned around. She slid the ring on her anal beads onto the bedpost and got on all fours. She braced for what came next.
After one deep breath she crawled forward. The anal beads popped out one by one. She let out a loud moan and collapsed on her bed recoiling from the mix of pain and pleasure. Rosalind took a moment to recover before whispering to herself, “fuck that was good”
She was a little less innocent after that and knew she would definitely be experimenting with anal again.
Thank you for reading, I’d love to hear any thoughts or suggestions and my dms are always open :)
Source: reddit.com/r/eroticliterature/comments/103cuod/learning_anal_23f_solofirst_time_analinnocent