Let me introduce myself I'm Jake. I'm a 23 year-old man, who recently got a place of my own. I decided to do a little bit of shopping for new underwear because I left mine in my parents home and I only have the pair I'm wearing and also to get some food and drink, for the next week or so.
I started with some specials which were right where I entered the store. Soon after that, I grabbed three packet's of five pairs of underwear (just plain cotton ones). After that, I just picked up some stuff to start my house; towels, cups, bowls that sort of thing. I then bumped into a old girlfriend, Ashley, who had moved away (that was the reason we had broken up). She was telling me she was back for good and I was telling her that I had just got a new place. I invited her to dinner and she gladly accepted.
I went to the checkout to pay for my stuff. I found it a little strange, when the lady gave me a glare then a cute little smile and giggle. I just ignored it, packed my bag and got a taxi home. I put my stuff away and started to run a bath, to celebrate my potential reunion with my ex girlfriend. I stripped down to my boxer shorts but as I took them off, they tore in half!
"Screw it!" I said.
I then hopped into my bath, cleaned myself up, got out, dried off and went to fetch my brand new underwear. I opened the packet and quickly slipped into a pair.
"What on earth is this?" I yelled.
I discovered that I had bought fifteen thongs and I nothing else to wear! I put my newly purchased bedding onto my duvet, then climbed into bed. (I just sleep in my underwear).
I was jolted awake by my cell phone ringing.
"Hello?" I answered.
"Hello, this is Ashley. I'm at your front door, can we talk about us?"
I quickly jumped out of bed, ran down stairs and opened the door, to see Ashley staring at my thong.
I was about to explain, when she gave me a kiss saying that I looked sexy with it on. She told me that she wanted to have sex with me.
I said, "Sure."
However, she had one condition. She wanted to ride my tight virgin anus.
I agreed but said that she must ride my ass first and then I was to get to do the same to her.
She said that she had to go and do something first, but would return soon. So I took the opportunity to clean up the house and also to masturbate, so that I would be able have sex with her for longer. She returned a half an hour later, with two bottles of lube, a six pack of condoms, a strap on and something else, which I later found out was a butt plug.
"We are going to have fun," she promised.
She put on the strap on and asked me to suck it, which I did but I was hesitant. After five minutes she put on a condom, which tasted like strawberries,
"Now, Jake, I am going to put something into your ass which may hurt but will ease quickly," she explained.
As she said, it did hurt some and I yelled out but there was bigger circles of the butt plug still to go in. The pain increased a little, then declined. She poured lube on me and asked if I was ready.
I replied, "Yes," and she then shoved a slightly hard, penis-shaped piece of rubber into my tight hole. It was agony and yet still pleasurable.
She then pinched my nipples which made me scream out, "FUCK ME!"
She just replied, "Oh, so you're a horny thong-wearing slut?"
I knew that was a lie but I went along with it saying, "Yes I am! Take my virginity with your dildo!"
Which she did, for what seemed like hours! When she finally finished, she stepped out of her strap on and said, "I'd better run, babe! Meet up with you soon and keep those!"Pointing to my thongs.
She ran out the door, leaving me on my living room floor, with a strap on in my ass, a condom-covered butt plug, unused condoms and lube!
To be continued...
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