Submissive's First Anal

It's Friday night and I'm returning home to see my boyfriend at his flat. He told me at the last minute to pick up a few bottles of wine, and I happily obliged. I love to please him.

I've dressed up in his favourite dress that he asked me to wear. It's strapless and tight fitting around my perky breasts and around my toned stomach. It flares out into a sweet layered skirt.

I ring the bell and he opens it like he knew I'd walk through at that exact moment. He smiles strangely and opens the door for me and I walk in. It's a comfortable place to me. We've been seeing each other for a few months.

As I walk into the kitchen I see the dinning room table is covered in a lot of papers, like documents, perhaps bills. The kitchen usually immaculately tidy is a little messy. It makes me a little uneasy. He's always in control and so ordered. I've never known him to be anything but.

He soon comes into the kitchen behind me. I notice his usual smart suit is disheveled and his eyes look tired. I feel immediately concerned. Something's wrong...

'How was work?' I ask, and he snorts.

'That's what I need to tell you. I got fired today. I'm completely screwed.' He says, kicking over a chair.

I stepped back completely shocked. The loud bang rings throughout the room.

'Euan, relax. It's going to be ok. You'll get another job.'

'You don't understand the company went into liquidation. They're not even paying me what I'm due this month. I just took the loan out on my new Merc. How can I pay for that?'

'Well I can give you some money.'

He laughs, 'On a waitress's salary. No offensive but I'd been banking on getting a bonus at the end of the month. I need to raise £15,000 by the end of the week or they'll take the house.'

I stood for a moment in silence, completely helpless. He drew me close and hugged me.

'I'm sorry to do this to you. I shouldn't have invited you over. It's not good for you to see me like this.'

'No let me help you.'

'Wish that you could. I'm sorry this isn't going to work tonight. It's best that you leave.'

I beg to stay but he's insistent and ultimately gets his way, like always, but this time I don't like it. Days pass and he ignores my calls. Finally I decide to wait outside his flat until I can see him.

Eventually he answers.

I practically get on my knees asking him to not ignore me, to let me help him find a way out.

'There is something, but you won't do it for me. I can't think of anything else. So much money so little time.'

'I promise I'll do anything to please you.'

He looks me straight in the eyes for a long moment. He knows I'm telling the truth.

Two days pass and I'm standing in his bedroom in front of a mirror in my best lingerie, garter belt and stockings.

'You're amazing. You really do love me, don't you?' He pushes his lips into mine and kisses me deeply.

'I can't believe I'm doing this.'

'Babe, he's on his way now, you can't.'

'I know.'

He kisses me and picks up the glass of gin and tonic, 'Finish this. It'll help.'

I obey. We look at each other. He's still wearing his tailored suit from work. He looks so good in it.

'You'll be just outside, right? But don't listen.'

'Petal, you'll be safe. Don't worry it won't change anything.'

The doorbell rings after I'd sunk another glass of gin and tonic. I feel a little lighter in the body and the head. I sit down on the bed. Soon steps come in. I see Euan for a moment as he pulls the door shut. The door clicks and I stand up without thinking. Too many nerves to stay at peace. The stranger smiles at me and scans my body. His smile widens.

I feel so vulnerable I want to run out the door, but I don't. I stay and let the humiliation build up a little. I worry about my lack of clothing. As I run my hand lightly over my tighs, to check my thong is sitting well, I'm suddenly aware of how wet I am. I don't understand it.

He's a tall man in his fifties, a little chubby but not terrible looking like the picture I'd made in my mind.

He checks the door is properly shut behind him and smiles as he approaches. His eyes never falter.

'Don't worry Princess.' He takes both my hands and leans in to kiss me. I'm stunned and I don't move. His hands start to explore and poke into my lingerie - at first on the top of it, caressing and massaging. A little rougher than I was prepared for, but I'd be lying if I said I didn't enjoy it.

He goes right for panties, and brushes the thin material away to get to my cunt and runs his finger up and down it, prodding inside. He takes his finger out and puts them towards my mouth. I look at him confused for a moment, before cupping my lips. He pushes his big thick fingers in and circles them. I start to suck, he smiles and moves them slowly back and forth, going deeper, and deeper and deeper, until I gag. He pulls them out and wipes his hand across the top of my tits.

'On your knees Princess. Now.'

I comply and kneel down. He sits down and takes out his cock. It's small and stubby.

'Crawl.'

I crawl over.

'Suck. Suck.'

I cautiously move my head over. As I shake slightly and begin to cup lips around it he takes my head and guides me. I suck and close my eyes. It doesn't have a bad taste. Quite good actually.

'Look at me. Look at me. Look at me!'

I open my eyes cautiously and I look up to him. He smiles and looks almost pityingly at me.

'Good girl.'

I continue to slide his hardening cock in my mouth, back and forth. My face is reddening. He pulls my hair, and moves my head back.

'Get on all fours.' He taps the bed.

I notice that my chin is dripping with saliva. I take a moment to get to my feet. It's awkward. I feel so self conscious. I get up to the bed and spread out like requested.

He moves behind me and I feel his large hands grab my waist and pull my thong down to my bent knees, then he runs his hand right around. I'm so wet. The bed moves as he gets up on to it. I hear a squeeze of a tube and then a cold wet finger touching my anus. He adds more and starts to ring my hole with the lube.

He pulls at my thong and I move my legs so he can completely remove it. He pushes my legs further apart and my head down.

I start to panic. It wasn't anal that I'd expected. I think about trying to say something but I don't know what. I don't want to disappoint my boyfriend, but I'd never let him do it the few times he'd brought it up. It just felt like it'd be too tight.

'Um, are you sure this is what you want?' I say hesitantly.

He grips me tightly, and I feel his hard cock against my thigh.

'You've got a beautiful virginal hole.'

I feel nervous and weak. I stop myself saying 'thank you' from my inbuilt politeness. Then I feel his finger enter and begin to slowly finger fuck me. It's a strange sensation. I let out a quiet moan as I try to take this strange sensation.

He stops and starts to grip my ass cheeks, spreading them and massaging them in his hands.

Then I feel the head enter, it's so tight, but he doesn't seem to care. He pushes it in. It seemed quite a small cock but just when I think it's all in there's more.

He leans over me and I feel his breath hitting the top of my back. He leans over and with both hands grabs my wrists and pins them down hard. Then he starts to thrust into me. It hurts. I naturally try to move, but he keeps going and going, and there's nothing I can do but take it. Soon he starts to pant louder.

'Oh you're so tight girl.' He says with heavy breath. 'How does it feel girl?'

I stay silent, embarrassed to speak, but feeling him continue to fuck me. He holds me tight with his cock all the way in. 'Well? Answer me.'

'It feels so good.' I say with a little moan. 'Please don't stop.'

He starts pounding away again, and I keep moaning. I can't stop it.

He has one final big push and lets out a tremendous sigh. He waits then gets up. I start to straighten out, and I feel a large hand spank me hard I lose my positioning and fall back down.

He snorts. I hear him get dressed and I wait with my ass in the air.

My hole feels sore and I can feel his juices dribble out.

Then the door opens and closes. I get up and put my dressing gown on. I walk over to the door and peer out in a crack in the door.

My boyfriend stands with the man talking jovially. My boyfriend's face is red, and I start to worry. The man hands him a large envelope. Soon the man leaves.

I feel so nervous about opening the door, but I don't have to as my boyfriend enters. He's smiling and he gives me a big hug.

'You're amazing. I love you.'

I hug him back, but I can't help notice his erection against me. My ass hole still stings and I feel dirty as I feel the cum drip down my leg.

His hands slide down me and I suddenly feel very nervous at allowing that man to take my anal virginity. I take the lead this time, which is quite unusual and go for my boyfriend's zipper.

'Let me suck.' I say sweetly. 'Please Sir.' He loves it when I beg and call him Sir. I never really understood it, but I'd come to enjoy it too.

He smiles and seems to agree.

Soon he's engorged in my mouth. I much prefer his cock and it feels so good to go back to it. I get a level of comfort and security from it. It fills my mouth much better too.

It's much sooner than usual that I feel that he's going to cum. I wonder what's happened that he's so turned on. I want to continue sucking his cock for much longer. I hope he can calm himself. I enjoy this too much.

'Spread your legs, lift your ass up.'

I comply and continue to suck. Trying hard not to make him cum, but he moans like he often does near the time and he grabs my hair and I know I'm about to get his load shot into my mouth. He cums and it's a lot. He lifts up my chin and he looks at me with my cheeks full. I swallow. He smiles.

'How's your asshole?'

I blush. Then I see that he's had a great view of it from the mirror behind. I look - it's red and dripping with cum. He doesn't seem mad and I feel relieved. I give him a hug and feel so special to have him as my boyfriend.