You have been seeing this new guy now for about a month. Something about his has your knees buckling just at the thought of him coming over. His voice just melts you like butter. You have taken great care in planning for tonight tho. He has shown interest in popping your anal cherry tonight and you think tonight’s the night you will give it.
Earlier this week you went to the local adult store and shopped around for some anal plugs. You asked the store clerk what he would recommend for anal training as you have never had anal sex before. He expertly gives you advice on which ones to try first. You make sure you have plenty of lube as well. You get them home and like a kid with new candy you open them up and inspect them. You pour lube all over the smallest one first making sure it’s nice and slippery. Then you pour lube over your fingers and rub it generously over your rosebud and in between your ass cheeks. Now or never you think as you take the anal plug and push it slowly into your awaiting hole. It resists at first and you feel a little bit of pain. You force yourself to relax a bit then push a bit harder and with a pop it goes all the way in. At first the pain is high, but it quickly subsides. You relax a bit and just stand there letting the feeling run through your body. You wonder what it will feel like while you walk around. So you decide your going to leave it in all day while you do your chores around the house. You get dressed in a mini skirt and tight shirt with no bra and panties. You love how naughty this is making you feel. The cool air running across your exposed pussy. Your nipples pushing hard against the tight top.
You go downstairs and start your housework. Just the movement down the stairs has your pussy starting to drip. You can’t believe how good the anal plug feels as you walk around. It pushes up against your pussy wall with every movement. After about 30 minutes of doing your housework you cannot take it anymore. You sit down on the couch and start rubbing your pussy. It doesn’t take long before you explode with your first orgasm. You quickly stick your fingers in your mouth cleaning them off. You love the way you taste.
The next day you look at the second anal plug you bought. The package you bought was a full anal training set. It came with 4 different size anal plugs all designed to help relax you a bit each time. You lube up the second one really well, and again rub more lube on the inside of your ass cheeks and around your rosebud. You take the plug and push it into the awaiting hole. This one is a bit bigger and takes a bit more effort to pop in, but you still manage to get it all the way in. You can’t believe how full you feel now. The pain is a bit more and lasts a bit longer this time. But you are determined to leave it there. After a few minutes the pain subsides again so you go about your day. This time tho you have to go out to do some shopping. So reluctantly you put on panties but still no bra. You love showing off your tits in public. You get excited when guys Lear at your chest and women are jealous at what you have. Your nipples are still rock hard and the anal plug is snug up inside you and not going anywhere. You put on a dress that goes down to your knees this time. You get into your car and start it up. The immediate vibration of the car sends shivers through your whole body. You almost cum immediately. You drive the supermarket first. You lost count but your pretty sure you cum at least 3-4 times on the drive. You worry now that have a wet spot from cumming so much. You get up to your relief nothing. But your pussy is dripping wet. You feel so naughty yet incredibly turned on. Your not sure how you make it through all your shopping without stopping to rub your clit some more but somehow you manage. You get home, and sit right down not he couch, pull your dress up, and start rubbing your clit through your panties. You have the most intense orgasm you’ve ever had. You an feel yourself squirt soaking your panties.
You continue this all week. Leaving the anal plug in longer and longer each day. By the time he comes to visit you later that week you have had the third largest plug up there all day. You never thought you’d like anal sex but this has shown you the most intense orgasms of your life. You wonder now how his cock will feel up there now and can’t wait.