Written by splatter

Fiction
23 Oct 2008


My whole life, I've always had lots of typical 'male' fantasies. But a few

years ago, I started having a recurring fantasy about a woman taking me

with a strap-on. I would be laying on my back, legs up and spread... with

her between my legs. Pretty much a reverse missionary position. I couldn't

imagine doing this with another man. But with a woman, Ahhhh... amazingly

erotic!! For me, the extreme closeness during sex... being linked *deep

inside* a woman... that has always been an important part of sex. And now,

I just wanted the experience from the other side.

Casual discussions with my wife pretty much ruled out living the fantasy at

home. But having just turned 50, I decided it was time... something I really

needed to do. So I took an ad with an online service describing my fantasy

and asked for any interested women to contact me. I had an immediate reply,

but she wanted her husband to be there to watch. I lied and told her I

had already found a partner. I then waited four weeks with no activity

before receiving THREE replies over one weekend. I eliminated one because

she was in her early 20's (too young). Another was scratched because I'm

pretty sure she(?) was in some stage of gender shifting.

But the third respondee was Anne... my age, lived about 60 miles away, had

strap-on experience and requested discretion. She was perfect! We swapped a

few emails, talked on the phone three times and finally agreed to a mid-week

afternoon triste at a motel half way between our homes.

After making contact with Anne, I began to question if I was really ready

for anal penetration?? It had been 30 years since I last had such sexual

play. So, I bought a vibrator and had three private sessions. I had

selected a small vibrator... I wanted penetration, but had

no desire to see what my capacity might be. Even with the small dildo, it

was not immediately comfortable or fun. But I learned to relax and was

able to fully insert the vibrator while masturbating.

In the past, Anne had regularly enjoyed using a strap-on with her husband.

But, they stopped the practice a year ago... and now Anne was keen to sample

it again. During our talks, we agreed that satisfying my fantasy was to be

the extent of our meeting and we wouldn't enjoy any other form of sex

together.

Finally our day arrived and we met in the motel room without a hitch.

We took our time, relaxed, sipped wine, chatted and enjoyed having actually

met. We gave each other a foot massage (having found that to be a common

interest) and Anne suggested taking a hot shower. We went together into

the bathroom, but only I stepped into the tub. Anne stripped down to

sexy bra and panties... lacy nothings. Because of all the focus on *my*

fantasy, it was first now that I noticed how sexy she was! She was almost

as tall as me, maybe a bit too heavy with smallish breasts. But her pretty

face and devilish smile completed an ideal partner.

She washed my back, chest and stomach with her hands... and dipped lower to

do a soapy massage between my legs. Finally, one hand walked across my buns

and slipped between my cheeks, while her other hand pressed onto my

back. I bent at the waist and leaned into the warm splash of water, hands

against the wall to steady myself. Anne provided a leangthy, sudsy teasing

before slipping a finger past my rim. Although we had been enjoying steady

chatting, we now fell silent while Anne used her fingers to delicately

relax and open me.

Once out of the shower, I was aware that we now had 'purpose' and we began

working to set the stage. It was here that we noticed the one problem

with our plan. I had brought along my vibrator, which was advertised as

fitting the harness that Anne brought along. But it just wasn't a match..

which left us to use the large dildo that came with Anne's harness. It was

only an inch or two longer than my *tiny* vibrator, but it was twice as

big around. I held the huge cock in my hands and slid my fingers along its

length. It was softer than my vibrator... a jelly dong, flexible and more

life-like. I laughed at the thought of having that go in me, but Anne was

very reassuring that it was going to be fine. 'Trust me', she said with

that suspicious smile as she fitted the harness. I watched as she tightened

straps... a bit disappointed that it wasn't *up*... not an erection, but

swayed side-to-side below... a clapper in a bell.

It took a bit of shuffling to get the right position. I sat on the

couch and scootched down so that my lower back was on the seat. Anne used

the other cussion from the couch and a pillow as a platform for her to

kneel on... getting to a comfortable height. She unsnapped and

dropped her bra... which we had discussed as being part of my fantasy.

Gravity worked on her tits... dropping them into heavy rounded bottoms.

Anne knelt close in front of me, using a creamy oil to lubricate the dildo...

stroking it as if to make it even larger. Finally, she leaned in

between my legs, holding the shaft of the dildo... and directed it to its

target. I stared at the device as it neared... and jumped when I felt

its touch. There was no entry, even though I felt it press direct on my

sphincter. Anne began a continuous cooing discourse telling me to relax

and how wonderful this was going to be. I closed my eyes and reached down

to feel the joining. Anne rubbed the cock head into me and squirted more

lube. I heard her voice rise to an expectation... and then go quiet.

I exhaled and relaxed. A second later I felt the head of the dildo slip

past the rim.... and poke into me. Open-eyed and gasping, I grabbed hold

of the shaft to stop its entry. *Ouch*

Anne restarted her soft vocal encouragement and began massaging the insides

of my thighs. I slowly rocked side-to-side, letting things settle to a fit

before letting go of the shaft. I began to answer Anne's cooing and placed

my hands on her hips, feeling her lean forward again. Slowly, the huge shaft

slid in deeper... one inch... this was uncomfortable, but not painful like

the initial penetration. Two inches... I felt SO full... and I began puffing,

shallow breaths. Anne paused... and pulled back a bit. She lifted my

legs more and began an in-out sway... slow tiny movements.. each motion

pushing in a tiny bit more before pulling out.

She made a longer thrust... inserting another inch (?)... and then repeated

the sway before again penetrating deeper. This was a slow process... how

much time it took I do not know... 5 mintues???.. 10 minutes??? But she

finally leaned heavily on me and lowered herself slowly. The dildo slipped

fully in and I felt Anne's hips press into my cheeks... Ohhhh..mmmmmmm...

complete penetration. *This* was what I wanted. Two people coupled so

that they could be no closer. I reached behind her... pulling her even

tighter and lifted my hips to ensure we were fully joined.

I now realized how much Anne enjoyed this... her eyes closed... maintaining

pressure, slowly rotating her hips... with small gasps and quiet moans

interjected into her breathing. I found that my hand was on my own cock...

but was surprised to find that I wasn't fully erect. I was heavily engorged,

but not stiff and upright. Why???

Anne finally whispered a quiet 'Yesssss', exhaled deeply and giggled. We

exchanged smiles as our eyes met and she leaned away... pulling half of the

cock out of me. This sensation was ENORMOUS... as if I was relieving myself.

But before I could say anything, Anne reversed the motion and again slid the

dildo fully into me. This was quicker and forced air from my lungs with an

vocal 'uuuhhh'. She pulled back again and repeated the thrust. For some

reason, I hadn't expected this. My fantasy was to feel the full coupeling

from a woman's view, but Anne was now actually *fucking* me! She repeated

the motions... increasing the speed of each thrust... forcing the shaft into

me harder each time. My cock stiffened... erect and throbbing... lifting

and pumping in unison to Anne's entries... each thrust filling my hardness

with blood, forcing it ever larger. I needed to pop my load, *NOW*, but it

wasn't happening... and Anne continued to enjoy our sex using a hand

to stroke my shaft with each plunge... dozens of thrusts... stretching me

for minutes... punishing me... repeatedly forcing the dildo into me...

until my heavy load was finally spewed onto my own stomach.

This signaled an end for Anne... stopping her thrusts and we slowly pulled

apart. I was amazed watching the huge cock emerge out of me!! We talked

about what happened and both agreed that it was something special. She

asked about repeating doggy style, but I declined... I wasn't even sure

if I'd be able to drive home as it was!

So how was it?? It was GREAT... waaaay more than what I expected. It was

also my only meet with someone from online, proving to myself that it can

actually happen. Would I do it again? Well, I still have Anne's phone

number...


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