Strap-On Adventure

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I've been seeing this new guy lately.
2.3k words
4.61
100.7k
65

Part 1 of the 2 part series

Updated 10/26/2022
Created 05/22/2010
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I've been seeing this new guy lately, nothing serious but certainly lots of fun. Two years ago I'd have laughed at you if you'd said I'd be in a casual-sex relationship with someone – but if I'm honest with myself that's the only way to describe the relationship I've got with Sean.

We met through a mutual friend and we hit it off immediately – I found myself very comfortable around him and he seemed very happy to let things develop in their own time – no pressure. It's let me be very open with what I want from our relationship and neither of us is feeling the need to take things to the next level of commitment, which is just how I want things at this stage in my life!

Sex with Sean has slowly developed from a fair beginning to something seriously erotic – I don't feel any real love between us but he sure as hell turns me on! He has a serious anal sex obsession which I have been happy to fulfil as I've become a bit of an anal freak myself! We've also been playing around with bondage a bit and he shares my love of toys, which is great, but what has really surprised me is that he loves me to use toys on him!

It's not something I've come across before with other boyfriends or really thought would turn me on – but how wrong I was! Just thinking about seeing his arse swallow inch after inch of dildo as I slide it into him has my pussy dripping as I write this!

Anyway, before I get too distracted here's my latest adventure...

I had been thinking of ways to surprise Sean and I wanted it to be something really wild, something kinkier than we'd been up to so far. The more I thought about it the more my thoughts centred round watching his arse get pumped, like he'd done to mine plenty of times. I ended up thinking "why not a strap-on?"

So after surfing the net and reading plenty of reviews I settled on a Doc Johnson vac-u-lock model with a couple of different attachments: a six inch dong with balls and a thick shafted, eight inch UR3 cock that got rave reviews for being so realistic feeling.

After it had arrived in the post I quickly removed it from its packaging to have a good look at it. Its design was a three-strap style that buckled around your waist, with another that went between your legs G-string style.

The black leather was soft and pliant and I couldn't wait to try it on. Quickly shedding my clothes I loosely did up the buckles and stepped into it. Tightening the waist straps first I then cinched up the third strap and felt a surge of desire course through me as the strap tightened over my mound and between my legs.

Looking down at myself I found the sight incredibly erotic and my hand slowly found its way down to the rubber cock jutting from my groin, slowly stroking and squeezing it as my anticipation of the evening to come increased.

I rang Sean and asked him to come round to mine for the night, that I had something special planned for him. He sounded intrigued and said he'd be round by seven.

When he arrived I opened the door dressed in my robe, gave him a passionate long kiss, then slowly parted the robe to show him my nakedness underneath - except for the leather harness strapped around my waist with 6 inches of rubber dildo protruding from my crotch.

The look of surprise on his face was priceless – and just the effect I had been hoping for. The look soon changed to one of desire as he stared down at the strap-on and realised what I had in store for him.

"Go into the bedroom and lie down" I tell him in a voice that leaves him little room to argue.

Entering my bedroom I'm sure he couldn't have missed seeing the restraints secured to the bedhead on each side - or the larger dildo lying on the pillows!

"Now lie down - face first" I say.

As he lay down on the bed I settled a leg either side of his torso, the smooth skin of my bottom settling on his lower back. I gently slid a blindfold over his eyes and then secured each wrist to the bed. I could feel my pussy begin to moisten as my excitement grew.

I slide down his body, the rubber dildo tracing the small of his back and down over his arse, until I am astride his legs. Grabbing some massage oil I pour it onto his thighs and begin to massage his legs, starting at mid-thigh and pushing upward, pulling apart his arse cheeks at the completion of each stroke. I notice a delicious shiver of pleasure run through Sean each time I pull his cheeks wide apart, exposing his excited arsehole to my view.

My hands begin to concentrate on his arse with circular motions, my thumbs tracing the bottom of his cheeks and up into the crack of his arse spreading the oil everywhere. As he groans in pleasure I can see his cock hardening beneath him in anticipation of what is to come!

With his cheeks spread wide I begin to rub my thumb slowly around his arse, circling his hole, then up and down his crack, with increasing pressure. With his cheeks still widely spread I quickly pushed my thumb forward penetrating his arse until I hear him groan into the pillow in appreciation.

"Get up onto your knees Sean"

Struggling without the use of his widely secured hands he ends up with his face pressed into the bedsheets and his arse very much exposed to my any whim.

"God that looks hot!" I groan from behind him.

As I move up behind him he jumps with a jolt of pleasure as I used my tongue to lick up his crack, then narrowed it and probe his twitching entrance. I feel his body shudder as I slowly push my tongue in and out, spreading moisture where it will soon be well needed, then slip a hand between his legs and quickly grip his throbbing shaft.

"Now stay still"

With a shiver of anticipation I kneel behind him and bring my dildo close to his entrance. Squirting some lube onto my hand I grip the shaft and start stroking it, imagining the feel of having a real cock to pump, then slowly press the head to Sean's arsehole. My hands go to his hips, gripping him firmly in my excitement.

"Oh God!" I hear him groan as he feels the head of the dildo push up against his hole.

My grip strengthens and l thrust my hips forward, attempting to bury the head of the strap-on into him, his bottom clenching involuntarily against it.

With a slow exhalation I feel him start to relax and my second thrust slips the head into him.

"Mmmm!!!!" I hear him cry out with his face buried into the bed.

"Oh baby, I like this" I say in a husky voice filled with excitement.

Changing my grip on his hips I begin to pull him back onto the dildo, while looking down and watching as his bottom slowly swallows more and more of the toy. My hips pushing forward force him to take inch after inch until his head lifts off the bed and he groans with the penetration, but my hands keep pulling him back as I force him to take the entire shaft, until I can feel my thighs pushing against his arse.

I groan with pleasure as I thrust my hips forward making him take every bit of the long shaft until my pelvis is mashed hard against his arse which applies a delicious pressure against my clit.

I begin to pull back, an inch or so and then push back in, setting up a slow smooth pace, each withdrawal another inch further, each thrust burying the whole shaft back into his beautiful arse. Before long I have the full length of the shaft withdrawing and I can see his arse gripping the flanged head of the dildo, before smoothly thrusting all the way back in. I then stop – with just the head held inside him.

"Are you enjoying this?" I ask.

"....yes" he sheepishly answers.

I reach my hand around and with a firm grip squeeze his hard cock, thumb stroking over the moist, dripping head.

"Yes – you are!" I say.

"And do you want more?"

Again he replies "yes"

"Like this?" I say, and I slam forward into him with a powerful thrust, the stroke only stopping when my hips grind into his arse.

"Oh FUCK that's good!" I hear him groan.

Taking that as agreement I begin a steadily increasing tempo, gripping his hips hard and driving into him again and again, harder and harder.

The feeling of being in control, of being the penetrator instead of the penetrated, sends delicious thrills through my pussy which is quickly flooding with moisture and I feel my orgasm building. Thinking of the times Sean has mercilessly pounded my arse to bring about his own orgasm, my focus settles on my own pleasure and I begin to hammer into him, crushing my pussy against his arse with every thrust.

Watching the shaft blurring into his arse, his body being shunted forward with my every thrust, I hear him grunting into the bedsheets at my assault. I can't tell if he is still enjoying this and the realisation that I don't care, that my pleasure is the sole goal, is invigorating.

"Oh god this is going to make me come!" I groan.

My pace lifts until I am slamming into his arse, trying to bring myself to orgasm.

"Ah... ah... ahhhh!" I cry as I thrust a final time deep into him and hold there, quite still for some time, my panting all I can hear as I grind my clit into his arse.

With my breath recovered I slowly reach a hand beneath him and feel his cock. He is rock hard and sticky with pre-cum and I realise he has been enjoying this, that it is perhaps time for me to bring him to orgasm too.

Slowly I withdraw from his arse until the head slips free with a sticky pop.

"Stay there! This isn't finished yet – I'd better take care of you hadn't I?"

Removing the strap-on I again begin massaging his arse, spreading his cheeks. As I hold his cheeks apart with one hand my other retrieves the larger dildo from the bed. At 8 inches long and a little over 2 inches in diameter it is a lot bigger!

"What are you doing babe?"

"Shush... just wait and see!"

Then I press the very soft and very large head against his dilated arse.

"Oh my god..." he stammers as he realises what I have in mind.

Slowly I apply pressure and the fat head begins to sink home and very quickly I hear Sean catching his breath as it spreads him much wider than the other dildo.

"Relax..." I tell him.

I see him give a slow exhalation which relaxes his muscles and the toy sinks deeper, until finally the huge head slips home. Groaning loudly I see his arse gripping down on the 2 inch shaft, just behind the head.

"Wow!" I sigh from behind him, my face near his arse – watching every thick inch slide in.

"I want to see you take more" I tell him.

I hear him whimper in anticipation and I begin to push more of the fat new toy into his bottom. The vision of this I find incredibly erotic, his arse spread so wide, tightly gripping the soft shaft.

He shudders with every tiny movement as I push it inch by inch into his arse, crying out with pleasure as I begin twisting it, turning it in full circles.

I can hear him grunting into the mattress as he takes more and more of the toy and with a final push I see that the entire shaft is now buried deep in his arse.

Shuffling beneath him I settle my mouth around his dripping cock head, his sticky pre-cum coating my mouth. I slowly begin to withdraw the dildo and as inch by inch withdraws I swallow more of his throbbing shaft, then pulling back my mouth I slide the dildo back into him.

I keep up this alternating rhythm until I feel his cock head at the back of my mouth, then relaxing I take him fully into my throat until his pubes are tickling my nose and I can feel his balls against my chin.

Holding his cock deep in my throat I begin to slam the dildo in and out of his willing arse until I feel his balls contracting above me and realise he is on the brink of cumming.

Not able to hold back any longer I hear him cry out "Oh shit babe!"

I feel his whole body stiffen, his balls constrict and his shaft swell as his orgasm roars through him and he pumps surge after surge of cum into me – 3, 4, 5 pulses pump straight down the back of my throat. I begin to slowly remove the fat toy while continuing to suck hard on his shaft, milking the last of his load from his still throbbing cock, a last squirt of cum jetting from him as the huge head of the toy pops free.

As I untie his hands we collapse onto the bed in the blissful afterglow of amazing sex. As I am nearly drifting off to sleep I hear him say – "You realise I intend to do the same thing to you in the morning..."

But that's for the next story!

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10 Comments
InfiniteXaosInfiniteXaos7 months ago

I am happy it is a mutual thing :) I hope we get to see him take her ass too c:

RangeExpanderRangeExpanderalmost 2 years ago

Lovely story well written!

c1999c1999about 8 years ago
Anon commenter - you do realize that Literotica is not...

only an American website, don't you? The author is most likely British and they use 'arse' instead of 'ass.'

Very nice story - well done!

AnonymousAnonymousover 8 years ago
So awful I had to comment...

First of all, 'arse' is NOT an attractive word. It is also extremely distracting that you use it in EVERY FUCKING PARAGRAPH! Writing is not your forte. I NEVER comment on anything and your story was so bad that I felt I was forced. Also, 'arsehole' should not even be a word.

AnonymousAnonymousover 11 years ago
strapon

Readingyour wonderfull depiction of strapon sex has me squirming in my chair, I would love to be the lucky guy

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