A First of Many

All my adult life, ever since I used to fantasise about my school teachers, I wondered just how hot it would be to bed an older woman.

Can anyone blame me? A confident older woman can be sexier than a girl of eighteen and I'm not talking about celebrities here, although there are plenty of prime examples. Older women have been there and done that; even what they might lack in looks, they can most definitely make up for in the bedroom!

Up until my mid-twenties I'd had the occasional woman my own age but the rest were always younger; I'd always attracted younger women because of my attitude. Truth be told, I'm not the most mature person you could know but I'm friendly enough and I don't pressure women into doing anything they don't want to do.

A year ago I got to fulfil this old fantasy of bedding an older woman when I met Terri online at a social networking site. One day I came across the profile of a forty-year old divorced woman with a wicked look in her eye and a statement saying that she was looking for a toy boy to make up for her ex's lack of effort over the years...

I sent her a message asking, 'if we met at a bar, would you let me get you drunk until you fancied me?'

We started to chat a day later, a week later I had her phone number and a few hours after that we were exchanging nude photos of each other.

She'd send a picture of her tits and she had massive round tits with long pink nipples you could suck on and never be bored of. In fact she sent me just about every picture possible of every inch of her. I couldn't believe a man would walk out on this... at the time!

I sent her pictures of myself and one I included was a picture of my rock hard erection. It was only a matter of minutes after that.

We were having phone sex when she gushed and told me that she wanted to have sex with me. I must be honest, I've never cared for phone sex but I like getting a woman all worked up and dripping wet by words alone, it's good for my improvisational skills.

And so a few months later when I managed to scrape up the cash, I was on a coach headed down South to meet Terri.

I was looking over her pictures on the coach on the way down, memorising her face, wondering what conversation a man engages in when he publicly meets the woman he's travelled six hours to fuck.

Terri was just over five foot tall with short black hair, the biggest brown eyes and the look on her face in every photo told me that she'd waited years to be fucked. She had a curvaceous, voluptuous body that I was dying to devour and she knew exactly how.

We were going to meet, travel to her flat and just spend all night having sex over and over again; that was the plan but I told her I also had other plans that would have to come first.

Because I was going to make her have her first orgasm by licking her pussy and I was going to make her gush all over my mouth.

I got to Hertfordshire at seven o'clock at night and she was the first person I noticed. The bus station was empty and few people could be seen wandering about. Terri stood by the bus stop smoking a cigarette and waited for me.

As I got off, I met eyes with her and smiled, waiting to get my luggage from the driver as he searched the compartment. Terri put out her cigarette and approached.

I got my bag and met her with a hug but typical luck, worrying what to talk about all day, the first thing to come out of my mouth was my tongue and we kissed slow, long and deep in the middle of the street for five minutes before moving on.

'I don't think I'll be able to walk straight all the way to your flat,' I laughed quietly and Terri felt the bulge in my jeans. She suddenly became shocked at the size of the monster I was keeping hidden from her.

'Fuck me,' she laughed, 'I didn't know it'd be that big!'

We rushed home and locked the door behind us. My bag went on the couch, our coats went on the floor, we stood in the living room and held each other, kissing deeply again and surrendering to our excitement.

I pushed myself towards her, my hands pressed firmly on her ass and felt the sensitive jingling of nerves as my stiffening cock awoke with the feel of her body against mine.

'What shall we do first then?' she asked me, looking deep into my eyes. I melted before the sight of this mature ex-wife as she expressed her excitement with a girlish grin.

'I think we need to take these clothes off and get into bed,' I told her excitedly and she took my hand, leading me through the flat to her room.

I'd dreamed of undressing her slowly and making love to her in between before we got down to the hardcore fucking and even told her about my desire to but before I could even remember, we were practically dragging each other's clothes off out of pure lust.

She pulled my t-shirt off and started biting at my nipples and kissing my chest, rubbing her hands all over me. I pulled off her top and began to kiss at the soft valley of her cleavage through the white lacy bra she'd put on just for me.

The bra didn't last long though; as she was unbuckling my belt, I was tugging at the locks, unclasping them and setting her free so I could play with them.

I pulled down her long flowing black skirt and marvelled at the sight of her, naked before me but for one single garment of clothing. A see-through white lace thong!

Pulling off my jeans, I told Terri to leave her thong on and placed her down on the double bed, also leaving my skin-tight boxers on as I crawled up beside her and began to kiss her again.

The room was dark but for a bedside lamp that she switched on so that we could see each other. Our bodies touched together, my roughness against her silky skin.

'Oh wow,' she said as I rubbed my straining, confined erection against her leg, pulling her closer to me, 'can't we just fuck first and get all this tension out of the way?' she asked.

'No,' I laughed and crawled between her legs, rubbing my hardness against her pussy through our underwear. 'I'm going to make you beg, I'm going to tease you until you're going crazy and then you can have this all you want...'

I got up on my knees and revealed myself to her, Terri immediately trying to get her hands on my cock and I let her. Slowly I peeled my boxers down to let myself free and she gasped in shock.

I had shown her photos already and told her that I was eight and a half inches long and thick but she must have thought nothing of it until now.

I spread her legs wide and began to trail kisses down her body, sucking on her nipples and squeezing them softly. Rubbing at her pussy through her thong I then began to kiss up her inner thighs, one at a time, until I decided the time was right.

I was talking her through what I wanted to do to her when I licked up the crease of her thong where her pussy waited and up to her clit.

The patch was damp and hot. By the time I was finished, it was soaking though and I continued to massage her with the tips of my fingers. I let one finger inside the crotch of her thong to feel she'd opened up to me already and with that I asked her if she was ready to go further...

She nodded and allowed me to peel her thong off. I immediately went in for the kill with my tongue and began kissing and licking away her pre-come.

I'd licked a lot of pussy before but she was sweet and I never thought I would enjoy licking a pussy as much as I did then.

I spread her pussy and began to suck at her clit when first Terri laughed as though ticklish and then began to moan, grinding her crotch into my mouth and nose. I held my breath and then went in deep, sliding my tongue as deep into her as possible.

I began licking her outwards, slipping in a finger and by the sound I could tell she was already dripping wet and coming. She was practically sloshing already.

The contracting of her inner muscles around my tongue and fingers indicated her first orgasm and I continued without stopping. Terri then took my hand and forced my fingers deep into her and began using my whole hand as a dildo replacement.

I watched in amazement as my whole hand began to disappear up to the knuckles and then beyond! She began to shout out in ecstasy as I felt and heard her wet pink pussy fill up and shower with ejaculate. She gushed all over my hand and face, panting breathlessly as she tried to regain control.

I began to lick her pussy again when she laughed and pulled me up on top of her, kissing me and licking my face dry.

'That was amazing,' she marvelled, 'but I'm going to be too wet for you now!'

I'd never heard that before and I told her, 'the wetter the better...'

'No seriously, I get so wet, you'll just end up slipping out of me, trying to fuck me silly!' she explained. 'But not to worry...'

Terri laid me down on my back and went down between my legs to where I stood at full mast. Because her hair was so short, I could see everything as she took my stiff cock in her little hand and fed it into her mouth ever so slowly. Her mouth watered profusely around me as she lay there with me only halfway in her mouth...

Wetting me from head to shaft, she began slowly sucking me further into her mouth before slurping at me and sucking her way back up to the straining head. I was in heaven, only seconds into it, this was the best blow I'd ever had already.

'You're going to get a lot wetter than you thought,' I told her as she began bobbing her head up and down, flicking me with her tongue and scraping me purposely with her teeth.

She brought her head up and asked me why. 'Because I'm going to cum gallons right up that soaking wet cunt of yours,' I told her.

'Promise?' she asked.

'I'm obviously going to have to prove it,' I said with my eyes closed and my hands behind my head, 'how do you want it?'

I felt her weight shift on the bed and she released her grip on the shaft of my hard-on and keeping my eyes closed, I felt her grip me again and the thick head of my cock meeting her silky wet pussy entrance.

I opened my eyes to look at her and saw her smiling, looking down at herself as my cock began to slowly disappear into her inch by inch. I closed my eyes again and heard the wet sucking of her pussy as it took me in but it was too much. 'Take it all in one go,' I suggested and she laughed again.

'I can't, you're really big,' she said and I sat up in front of her, continuing to suck on her tits as she tried to take me in.

'Lie on your back, I'll take care of us,' I told her and positioned myself between her legs. Holding her in my arms by her shoulders, I positioned myself right at the dripping entrance to her pussy and slipped myself in slowly, listening to her gasp.

One inch at a time I began to fuck her gently, and when I was halfway in I forced myself into her, causing her to inhale sharply and drag her nails across my back. Her pussy slurped wetly as I drove in and I felt myself sprayed by her come again.

Our hips grinding and our pelvises joined tightly together, I asked Terri if she was ready and began to gently buck at her, again fucking her with half my length as all of it glistened, coated with her juices.

'Oh fuck you're so big, fuck me, please,' she gasped as I began to increase length and speed. In the missionary, we fucked for almost an hour.

I lifted her legs up to my shoulders so we could get deeper and now that she was opened to me completely, we started to fuck in every position we could think of. I just couldn't come to a climax but didn't care, I was enjoying making her orgasm over and over again, watching her beg me to stop and then for more.

I took her from behind, grabbing her by her huge ass and forcing myself into her tight pussy and was coming close. Terri told me she wanted to finish off one way in particular this first time around and I agreed without knowing what...

She lay on her back and pulled out a ten inch long vibrator and began to fuck herself with it in front of me, she then asked me to lie sideways so that I could fuck her pussy and she could hang her legs over my side.

So I was fucking her sideways while she duelled with my cock and her vibrator. Her pussy was filling up again and I could feel her pussy walls beginning to strangle the shaft of my cock.

Terri screamed but then carried on, unable to stop crying out as we fucked loud and hard. I looked down to see her come spraying and splattering us both as it came out in huge hot liquid squirts.

I got on top of her suddenly and began furiously tugging at my length as she encouraged me to come all over her tits and I exploded all over her.

I fell on top of her almost, gaining my balance breathlessly and lying beside her as my erection began to subside. Terri went down again to suck me dry of both our love juices and came back up to kiss me gratefully.

'Oh my god, where did you learn how to fuck like that?' she asked me, snuggling up naked next to me in the dark.

'Nowhere, it just seemed like the right thing to do,' I explained breathlessly; I was close to passing out for all the effort I put in.

'I want more,' she said and laughed but then immediately after, asked, 'cigarette break?'