I have always been shy, innocent girl. Before my 24 I had never had sex, I even didn’t have a boyfriend and never kissed anyone. Until my first boyfriend. We have some difference in age, but it doesn’t matter.
One day, as usual we were having sex, talking… I always knew he is very open-minded, but that day I found out that he is actually bi. And I started to be curious and ask a lot of questions, how is it for him to be on my place. He told me that he likes when someone is behind and anal sex. And I started to imagine how is it look like and what more is that what if I would be that person from behind.
The day after I started to search online sex-shops looking for couple toys, dildos… when I found that Loving Joy 8 Inch Vibrating Hollow Strap On.
“Strap on! Yes this is what I need!” I said to myself, “Wow, this one is even with vibration, let’s try.”
My thoughts continued “Wait, I remember our lube is almost finished, and for that thing we’ll need it for sure. Okay, let’s see…”
“I don’t understand anything in that…” almost crying from a variety of lubricants and not knowing which one is better. “Ok, I remember he was saying that for anal is better silicone lube, let’s try this. Oh, the same brand as the strap on Loving Joy Silicone Lubricant. Amazing.”
I ordered those 2 items and could already wait for them to come. For my big surprise it came super fast and right on-time, as we were supposed to meet this evening.
The evening was usual, nothing special, the only thing Adam noticed my bag and said
“Eve, why do you need that big bag? You have never worn something like that.”
“I have a surprise for you.” I smiled
Then we went to his apartment as usual, and I couldn’t hold myself anymore. As soon as we started to play with each other, I took out strap on from my bag.
“Let’s try something new today. I want to be behind you today.”
By his face I saw he was surprised, but at the same time pleased.
“Oh, Eve, I would love to. I actually very surprised, I couldn’t expect this from YOU.”
As Adam helped me adjust it into position, he brushed his hand under the dong and across my smooth pussy lips. I was getting damp and my eyes were beginning to glaze over.
Knowing that things might get 'messy', he took the towel and spread it on the bed. He warned me that there would probably be some 'stuff' on the rubber cock after we finished. I understood, but it didn't matter to me. He reached into the nightstand and retrieved one of his condoms. He unwrapped the foil and began to apply it over the head of the big dildo. A shiver went up his spine as he slowly unrolled it down the length of the shaft to the triangular base, which was fairly secure over the clit and mons. I opened my bag and brought out a tube of lubricant. Snapping the lid open, I squeezed a generous amount into the palm of my hand. I applied the lube over the head and down and around the shaft carefully.
"It feels like the real thing, Adam," I said proudly. Then looked for a place to wipe off my hand.
"Better use that on me, Eve. I'm going to need plenty of it if your 'cock' is going to fuck me." he said.
"Good idea," I said.
He took the position on his elbows and knees on the bed, the towel under him. He rested his chest on the sheet, fully exposing himself to me. I wiped my hand over my puckered hole, gently inserting one, then two fingers up his clenched and waiting hole. As I fucked my fingers in and out, he tried to relax as much as possible. I wiggled my fingers in his ass, loosening him up slowly but surely. I kneeled down on the bed and knee-walked up to him. He looked down between his legs, watching the dangling flesh-colored pole sway from side to side as I approached. I tried to move carefully, as it was me down there. He immediately ordered it to relax, concentrating hard to make it so. He reached down to fondle himself as I lined myself up to his butt and pushed the head against his hole. It felt like it would never fit in there. I began to tease his hole, gently poking at it several times, until the head began to enter. I gave a big thrust, and the head popped inside him, taking his anal cherry.
"Stop, stop! God, you're going to rip me in two!" The pain and pressure was incredible!
"Should I pull it out?" I asked. Before he could reply, I pulled out, doubling the pain but relieving the immense pressure.
"Arrgghh.." he moaned. "Put it back in, but slowly, Sweetheart!"
I pushed the head of the monster back in him.
"OK, push in a little more, but only an inch," he instructed. I slowly moved my hips forward, driving the cock into him.
"I'm not used to being the man," I said. "Is my rhythm OK?"
It felt so weird, but so hot. He was moaning, moving with me, answering on my movements.
We were keeping the rhythm until he collapsed on the bed, and my cock pulled out of him.
“Did you enjoy?” I asked not confident.
“Oh, yes, thank you so much for that surprise. I has been a long time I didn’t get fucked, you did great job.”
We cleaned ourselves and started to think what to new next time.
