10 Oct 2017
Her first anal was not with her bf
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E is a girl I have known for some time now. She has a boyfriend but I am the friend on the side. We were introduced by a friend and started chatting, pretty soon the conversation turned sexual but she was adamant that we would not be engaging in any sexual activity. Well as you can imagine we didn’t keep to that rule and since we first started “seeing” each other we have fucked numerous times. She is on the pill so we play without condoms and I have sent her home many a time with a hot load inside her. I have also helped her achieve two major firsts in her life; the first time she swallowed and her first anal experience.
This story is about the latter.
A while ago we met up for breakfast and afterwards we went shopping (she needed a few things). In our country we have a large chemist change, similar to CVS, and while walking through there we found ourselves deciding what lube to get. There were limited options but a squeeze bottle of Durex lube found itself in our basket and we continued on our way.
We had planned to use the lube a few times but the chance just didn’t happen. She was very nervous about anal and I didn’t want her to be left sore (her bf had tried a few times and left her in pain… but he never used lube. I had kept the lube in my laptop bag ever since we bought it but as I said we just never got the chance to use it.
About two weeks ago I decided enough was enough, I needed to fuck that virgin bum and I needed to do it that day. I told her to come to my office as I would be “working late” and since my company is small the open plan office would be empty. I cleaned my desk and made sure her favourite spot would be cleared (she loved being bent over my desk and it wasn’t the first nor the last time she would be). She arrived 30 minutes after the office had closed and I met her at the door. I greeted her and walked her down the passage towards the open plan office but half way down the passage I grabbed her, pushed her up against the wall and started to kiss her passionately. I took her phone out of her hand and slipped it into my back pocket as I used my free hand to hold her hands above her head. Soon she was moaning in my mouth but I was kissing her so fiercely she was gasping for air and whispering “oh fuck” every time I moved my lips to her neck. I finished kissing her by biting her bottom lip and watching her eyes roll back as they do every time I do this.
I took her hand and led her to my desk. I pushed her down into my chair and unzipped my jeans, freeing my cock from its confines. She leaned forward and took it into her mouth in one go and started to suck it like she had missed it, like a long lost lover. After she got it nice and wet I pulled her up and bent her over my desk. I pulled down her panties and sunk my cock into your dripping pussy. While I was fucking her pussy slowly I grabbed the lube (which was close at hand) and lube up a finger. I pushed my finger into her little rose bud and it went in without any problems. She let out a moan with an “oh fuck” as my finger went in deep. I fingered her bum for a few strokes before I pulled out and pushed in my thumb. Her hips bucked as her body told me how much she loved it. She was moaning constantly now and I decided that her bum was ready for my cock.
I told her I was going to put more lube on my fingers but I needed to pull out. She was barely able to comprehend what I had said but gave me a sound that sounded like she agreed. I grabbed the lube and lubbed up my cock then pushed it into her little bum. Her moan came from deep within her soul as my cock slowly entered her. I put my hands on either side of her and her hand found mine and she held on as my cock ended up balls deep inside her tight little bum. I whispered into her ear “my cock is completely inside you.”
She wasn’t able to comprehend what had happened but after a few moments she managed to gain some composure and I asked her if she was ready for me to fuck her. She nodded and I stood up, gipped her waist and started to fuck her. I started slowly, letting the lube not only cover my whole cock but also lube her up. When I felt she was ready I picked up the past and started to fuck her hard. Her legs were hitting the desk, and the desk was hitting the one behind it but this noise was not loud enough to cover the sound of her moans.
After about 15 minutes of fucking that tight little bum I decided to change the position. I made her lie on her back on my desk with her legs up in the air. I looked at her little bum and you could tell a cock had been in there and then promptly sunk my cock into it again without warning. She gripped the desk with all her strength as my cock was now able to get deeper into her and her facial expressions told me how deep it was going. Her face and her moans were enough to send me over the edge but the thing that did it was her words. She begged me to fill her bum with my cum. I gripped her legs and started to fuck her harder than I have ever fucked any hole in my life and soon I emptied my balls into her. I kept my cock in her for a couple of minutes and then slowly pulled my cock out. I kept her legs up and put her panties back on her. When she stood up her dress fell back down and hid the marks on her legs left by the desk.
I sent her home after we chatted for a while and she messaged me later in the night saying that my cum was still in her.
She is coming to my office today for another good little bum fuck.