Masturbating With Annie

I enjoy the simple pleasures in life. The odd hand hold, the chat with a friend, even something as simple as washing my hair. I love it. There is, however, one simple pleasure that I keep going back to, time and time again: Masturbation.

I love everything about masturbating. The feeling of it, the sensation of my cum surging up and out of my cock. I like every type of wank: there’s the slow ones where you just go at a really slow pace, enjoying the journey. There’s the quick ones before you go out, just to relieve some tension. And then there is my favourite type: The mutual one.

I remember my first mutual masturbation session.

I was 16 and going out with a girl called Annie, also 16. We were, one day, just fiddling about with each other, fondling body parts, discovering what each other likes. A little bit of kissing, too. It escalated pretty quickly, but neither of us was ready for sex. We did want an orgasm though, so we undressed each other and continued our exploration.

Annie watched in fascination as my cock went from semi-hard to harder and twitchy. She couldn’t tear her eyes off it. I couldn’t tear my eyes off her breasts. I think that’s where I got my love of breasts from. Hers were just so lovely. They were little pear shaped things, big enough for a handful. The nipples had this really arousing pinkish brown colour to them. I kept staring at them and it seemed like her nipples just got harder and her breasts more firm, just from me staring at them. I was fascinated by the pinkish colour flushing through her from her face right down her neck towards her breasts. It made me want to kiss her all over.

“Can I?” Annie asked, extending a had towards my cock.

“Sure,” I gingerly replied. I was so nervous and yet so turned on.

Annie’s hand grasped and closed around my cock. Emboldened somewhat, I reached out and took both her breasts in my hands. They were so firm, yet soft. Her hand felt quite amazing on my cock. I’d never felt anything like this before. My pulse was rushing and my breathing erratic and ragged. This all felt rather surreal.

Annie was always quite shy, but this just seemed to make her come alive. She stepped closer and rubbed my cock against her pussy. My cock head brushed against something that was a different texture to the rest of her pussy. It felt... hard? Kind of like a small penis. We later found out that the small penis-like thing was her clitoris.

Her grip on my cock tightened, but she ceased movement of her hand. She just stood there holding it in a vice-like grip. I hadn’t even realised that her bedroom door had swung open and her sister was standing in the doorway gawping at us. Once I noticed, I froze, just as Annie had.

“I’ll just excuse myself,” Emma backed out of the room, “sorry.” Her embarrassment was clear to see.

“Bitch!” Annie cursed.

Her grip on my cock loosened a bit and she went back to jerking it. My hand explored between her legs and Annie let out a sigh. I thought I was doing something wrong and stopped.

“Do that again, that was good,” Annie smiled at me.

I wasn’t even sure what I was doing, but she told me not to stop. It was that little hard bit that I was playing with. I stroked it with one finger and then started to move away from there. I wanted my fingers inside Annie.

I moved in closer and by this time Annie had released my cock and was concentrating on what I was doing with her. My cock nestled in between her pussy lips, but didn't penetrate. Annie started to rub the underside of my cock and it felt... Amazing! I started moving my hips and my cock went along her pussy lips. With her hand on the underside of my cock, she was guiding me to where felt the best. She pulled me closer to her and started squeezing my butt. 

Pulling away, she told me, “Watch this!”

She laid down on the bed and spread her legs wide. Her fingers went inside her pussy and fucked her hard. I sat next to her and started to wank my cock. Fascinated, I watched as she fucked herself with her fingers. I was quite close. I needed to cum, desperately.

“Finish me off, just do what I did,” Annie told me.

I kneeled down in front of her on the bed and stuck a finger inside her. I slowly drew it out and back in. I was afraid of hurting her.

“Do it really fast, don’t worry, you won’t hurt me!”

I took her advice and started fucking her fast with my fingers.

“Curve them a wee bit and get that cock over here!”

I was amazed at the transformation, how could she go from shy wee shrinking violet to, what could only be described as, quite domineering? I shifted around and we found the perfect position. With my fingers inside her and Annie’s hand on my cock, this all added up to one hell of a scene. Every time I thrust my fingers inside Annie, I heard a squelching sound and she let out a soft moan. Her hand was gliding up and down my shaft and I hadn’t realised at the time, but I was thrusting in her hand, too.

“Keep doing that, I’m close!” Annie shouted at me.

My fingers were getting a little sore, but I kept going and stroking the inner walls. One of my fingers stumbled upon something with a different texture again. It felt softer. Every time I grazed up against it, Annie would squirm and grip my cock tighter in her hand. I knew instinctively that I was onto something and kept fucking and stroking this soft bit, meanwhile, Annie had started massaging my balls and working on just my cock head. I wasn’t too far off cumming, but I wanted both of us to cum together.

“Are you close yet?” I asked Annie.

“Just keep doing that, I’ll cum in no time!”

“As long as you keep doing that, because I’m gonna...”

I let out a sighing groan and cum surged up my cock and out, hitting poor wee Annie in the face. She didn’t seem to mind because it looked like it sent her over the edge. Her pussy clamped down on my fingers and her legs clamped on my arm, keeping it where it was. Her pussy was so tight, I couldn’t even move my fingers!

“Good Lord, that was amazing!”

“It was, wasn't it?” I said, collapsing on the bed.

We continued fondling each other and Annie wiped the cum from her face. What she did next surprised both of us: she looked me straight in the eye and licked the cum from her hand.

“Man, Annie, that was fucking hot!”

Annie just laid on top of me and took my cock in her hand. She licked the dripping head and savoured the cum that was oozing from it. Her pussy was right in my face and glistening. I’d never seen anything more arousing in my life before! My tongue went out and licked at the shiny liquid. It tasted peculiarly lovely. I can’t think of how to describe it, sweet and salty and yet a little bitter, too. It was fucking delicious. From that moment on, I was hooked on her pussy juices and went down on her at any given opportunity. She seemed to also be hooked on my cock and sucked me off at the drop of a hat. We had some amazing 69 sessions, but that might be another story.