Lucy was who I considered to be my first 'proper' girlfriend. That is someone who I actually had a relationship with rather than just a fumble. All together we were a couple for about 5 years, but in the end it just fizzled out.
At the time, she was the best sex I had. She knew what she wanted and liked to get it. I was happy to be along for the ride. In the grander scheme of things, the sex was very straight, but unknown to her it would be Lucy who would unlock my interest in arse-play.
We had been together about a year and we decided as young couples do that we needed to buy a sex guide book. The one we chose was pretty crap, but it told us all about the perineum and what fun stimulating the anus and g-spot can be. Well, we had to try it.
Lucy is about 5'7 with long curly hair (always a treat to get my come in there!!) She had a good figure with cute 34B tits. I would love fucking her, especially in her favourite position, her on top. It was in this position that she would ride me and as we reached climax I would wet my finger and poke it into her arsehole. This would inevitably set her onto her orgasm and I was never far behind. I loved the way her little hole would pinch on my finger and it would slide in and out on its own accord as she humped me. For my part, there is only a small amount of skin separating the vagina from the anus, I loved feeling my cock rubbing against my finger as we fucked. Sometimes she would put her finger in which was better for me, but she was less up for this,
The best bit for me though was the reciprocal action! She would blow me and lube up my arsehole with some baby oil. She was a pretty good cock sucker, but would get tired of it. No problem for me, I would let her wank me while we 69'd then as I got closer she would resume sucking me.
I remember one particular time, she was staying at my place, I lived above the shop where I worked. I was due in work in 5minutes and she was feeling naughty. I said I had to go so she said that if I wanted one, I could have a 'special.' She pulled out the baby oil to prove she wasn't bluffing and I was back on the bed quicker than you can say 'late again!'
I was not hard when I lay down which was brilliant. I love the feeling of wet lips on my soft dick, it gets so hard so quickly! While she worked on the head with her mouth she squirted oil on my balls and I moaned as I felt it run down my arse crack. I obligingly opened my legs and her hand worked its way up my thigh and worked its way between my cheeks. She never usually starts on my hole this early, so I was feeling really horny. She was teasing my hole with her finger tip. I could hear her giggling as I tried to wriggle my arsehole onto her finger. She pulled her face off my cock and asked me what I wanted, "I want your finger," I replied. What did I want with it she asked, what should she do with her finger? I was getting desperate now, she had been teasing my ring for so long, "I want it in me," I said, "I want you to put it my arsehole!"
Oh, was her reply and she leant down to whisper in my ear, "You want me to finger fuck you?" Lucy rarely swore so hearing this dirty question come from her lips was amazing.
"Yes" I replied without hesitation, "Finger fuck me please!"
She sucked my cock again then said, "Pardon?" I replied again and again she sucked my cock, "I can't hear you," she said.
I replied louder, "Please fuck me with your finger, come on, please put it in me"
She pushed on my hole and said, "Louder!"
I needed that finger in my arse now! SO I shouted it out, "Come on, Fuck me, FUCK MY ARSE WITH YOUR FINGER!" She obliged this time and I felt her finger sink into my arsehole as she sucked down on my cock once more. My cock had got so hard, I wanted it more, I was going to come soon. "That's it," I shouted, "FUCK MY LITTLE ARSEHOLE, GIVE IT TO ME!!" Well she certainly did. My cock was firmly in her mouth and she added another finger to my tight arse. I felt her hit my g-spot and was shouting for her to FUCK MY LITTLE HOLE as my come started shooting down her throat. Heaven!!
I kissed her deeply as I threw on my clothes (I love licking my come out of a woman) and left her on the bed as I ran down the stairs.
My boss was standing outside the shop as I approached just tucking my shirt. "Sorry I'm late," I began, "but..." He held up a hand to cut me off. Shit I thought, he must be really pissed. Then I realised that he wasn't holding a hand to stop me talking, but was pointing up. I know a look of horror fell across my face; I looked up to see my bedroom window open, Lucy was there and she gave me a wicked grin.
I looked back at my boss who just smiled. Apparently I have never been redder since that day!