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Member Since: 9-Jan-07
Location: US
Posts: 112
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Just getting started
My boss' DP fantasy
Years ago I dated Silvia. Well, we weren't dating, we fooled around after quietly lusting for each other while dating friends.
We were in the shower one night. Her tight body was always a turn on, so with water rolling over her milky skin..... down her back, over her curves... I had an urge I never had before.
I cupped her tiny breasts and pressed against her. My growing member responded to the slick pressure. My hand went to her neck and I pulled her head to me and we kissed. She was surprised but gasped with the heat of unknown delight. Her hips ground against me.
I ran my tongue down...down,,,down... to the base of her back... I thought "am I going to do this?" and my cock said "Hell yes!" I ran my tongue down her crack until I found her anus. Her body writhed instantly as my tongue caressed her.
"Ahhh fuck!"
Our hands played with her vagina as I licked her ass. Silvia's legs wobbled as she orgasmed,
For the most part that was all the anal play I've ever done.

Until last month.

My boss Rachel and I have been fulfilling each others fantasies during business trips. I'll link my other stories below if you want to build up to this story.

Rachel's husband is a way older and she's at an age where her hormones are in overdrive. She is ready to go all day. Needless to say hubby isn't cutting it. Rachel also has kids, so years of ignoring her needs, quiet orgasms and raging hormones have led to unbridled desire to have fun. I thank god everyday she decided I'm the one she wanted to have fun with.
She still holds her moans back, but there's something sexy about it. It's a reminder that she's holding back the moans because she's letting go of everything at home for her own pleasure. It's unbelievably hot!

Rachel introduced me to her vibrator. We named it Scott, after a co-worker that isn't particularly smart, but Rachel has fantasied about. Scott joins us a lot.

On our last trip Rachel told me Scott has spent some time in her back door. I've never been an anal guy, but the thought of Rachel, her beautiful body... I felt a stir of excitement at what could happen.

We did some porn watching. There is nothing like pleasing a woman with your tongue and have her say "That look fun, we should do that." to a pornhub videosmile

We took our time. I had a drink, She had a gummy. We chilled hard.
We took a shower and eased into the nights fun. I ended up on my knees pleasuring her. I turned her around and pushed my face between her ample flesh and tongued her, my hands wrapped around her thighs as she played with herself....

On the bed we 69'd for a bit. My fingers teasing and caressing her.

Later, on her knees, Rachel pumped her lush body on and off my cock. She'd pull away just enough for the tip of my cock to rub her wet lips. I'd guide myself up and down her full lips, then with a little nudge and a wiggle of her hips, I'd watch her lips glide down my shaft. I ran my thumb over her anus. gently pushing, rubbing.
As she got more excited and her body writhed with enjoyment, I generously rubbed some lube into her crack.
My slick thumb caressed her tight little anus as Rachel wiggled, moving my stone hard cock around inside her. She arched as my thumb pressed on her tightness, just barely breaking the surface.
Rachel rocked forward, I slid my cock out and pressed it between her ample hills. I pressed my hot, wet shaft down along her valley. She twerked a little... holy shit! Her undulating body, my solid hard cock rammed between her cheeks and understanding where we were going filled me with anticipation and a rush of desire.
I grabbed hold of her hip with one hand, my cock with the other and found her eager lips. I sank firmly until I could get no deeper and then pulled her to me. Her knees off the bed, I wiggled and thrusted and she took tiny "fuck me" pants.
With her knees back on the bed I grabbed on to Rachel's wide, beautiful hips and thrusted, long, hard, booty clap thrusts.
and again.
over and over,
My thumb caressed her crack, teasing her hole...
Rachel's arms splayed as her head sank to the pillows. Her beautiful ass up and eager.
And with a little push my thumb sank in.
I gently went deeper
"Hhooo muhgod..." she moaned into the pillow.
I pulsed my thumb gently up and down. Her back and hips undulated in her bliss, enflaming my lust. Her pursed lips hugged my slick shaft. My fingers held onto her flesh as my thumb pulsed inside her. I want to cum as I write this.
"Mmmmmothah fuhhhhh..."
Moments later Rachel pulled away and turned to me. Her look said it all.

On our sides, Rachel in front of me we guided my lubed cock. It was so sexy to feel her fingers wrapped around me, slide my head between her cheeks.
I held her hip as my head found that tight indent that said you've found the place. She wiggled, I pushed. The ridge of my crown pushed its way in and it seems like it went from I'll never fit to my head popped in.
"wwhoouhuuhhh. holyfuk... holyfuk..."
I'm not gonna lie.... holy fuck. feeling her squeezing just below the ridge of my head.... holy fuck.... I'm surprised I didn't explode.
I pushed and like a tight little fist sliding down my shaft, I felt exactly how deep I was. She panted quickly and tried to talk...
"huh huh huh... slow slow... holy fhhuk.."
Her hands dug into and bed.
"Hoyeahh... fhuugk..."

I pressed against that beautiful ass and wiggled until I felt her tight ring inch closer to my base.
"hoo Muy ghod..."
"Fuck yeah..."
I pulsed my hips and wriggled as she panted, trying not to be too loud. We slowly found a rhythm, I held onto her thick hips as she purred.
I've done so many things, but this was a first for both of us. Rachel was in her own world of ecstasy.
Mouth open, panting.
Eyes fluttering as I slid in and out.
Her fingers rolling her nipple, playing with her heavy breasts.
fingers on her clitoris...
Her body vibrating with excitement.

Rachel reached for Scott.
As she edged Scott into her it was like the intensity went to 1000.
"HooooMmmmghuhhhh!" Rachel twisted her pelvis all over, scratching an itch she's had for years. Her womanly curves undulated with pleasure.
My god feeling Scott inside her was something I didn't expect. Wow! It was hot to feel that alone, but the whole experience was mind blowing. I drank in Rachel's heaving body as she quickly got closer and closer.
Her tight hole stretch around me as I pumped my thighs, slapping against her beautiful ass.
"huhuhuhuhuhuhhhh fuhme,...fuchme..."
My god I wanted to cum.
But I couldn't get leverage no my side, and her hips are so much wider than me I was going up hill.
Our conversation on threesomes and what positions she wanted to try came back to me. She said "If we're doing it right, It's not up to me."
So I pulled out.
She looked at me like "What the fuck?" until I pulled her thick body to the crown of my cock. On my knees, One hand on her thigh, one on my shaft, I found her spot and felt my cock sink in.
I used her creamy thigh to pull while I pushed. Her body arched, her mouth opened wide as I sank into her. She was close. I was close. I wanted to hold out because I wanted her to cum like this so badly.
I pickup up the pace. her thick milf ass, her delicious breasts shook with every down stroke.
My god She is beautiful. So hot, my eyes followed her bouncing, quivering curves.
Her foot began to wiggle, her thigh and ass shuttered as her pants became high pitched.
I reached down and took control of Scott.
My god what a sight. She immediately reacted. She squirmed like she was reaching to grab her orgasm. The wave was so big, so immense, she completely let go and lost all control. Her words went away, her eyes rolled as she squealed breathlessly.
Her foot wiggled, her body shook like her orgasm was an earthquake coming from her hips.
I lost it.
I took a last few long, from tip to slap strokes to feel her tight grip stroke my full shaft.
"Oh god ohh fhuk... ggghhhghhhh!"
Deep in her I came so fucking hard I instantly wanted more of her.
She let out a scream that probably woke up the whole floor, but fuck them.... She was cumming like she'd wanted for years and it was sexy as anything I've ever seen.
Rachel turned every shade of red as her body writhed uncontrollably. After a few moments she put her had on mine and eeked out a "whait..." I stopped and watched her ride out the aftershocks of her orgasm, her twitching muscles still gripping my swollen shaft.

Needless to say that was not the last anal night of that trip.

I hope you liked what I'm writing. leave a comment if you do.

Here's the other Rachel posts. Let me know if you try to survive all four. I just tried and..... wink

#1 The first time

#2 Back at it

#3 update with a tease

If you want to read about Silvia, here's how she and I hooked up.

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Member Since: 12-May-08
Location: US
Posts: 83
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You lucky man!!!

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Member Since: 21-Dec-18
Location: US
Posts: 680
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I'd love to take Scott's place in that scenario if you're ever in my area. Or if she wants to keep Scott in the game, I'm available to help her experience "air tight".

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Member Since: 9-Jan-07
Location: US
Posts: 112
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crazy17222 said: You lucky man!!!

TY! I thank god every time she's into getting together again.

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Member Since: 9-Jan-07
Location: US
Posts: 112
Forum Level:
Just getting started
legsfeettoes said: I'd love to take Scott's place in that scenario if you're ever in my area. Or if she wants to keep Scott in the game, I'm available to help her experience "air tight".

TY! Yeah, we've talked about it. Believe it or not from my stories, she's actually pretty reserved. The only reason I'm lucky enough to be welcome to her beautiful body is because I've known her for years. Even Scott, the real Scott, is just too much for her to deal with. I'm ok with that. Whatever she wants, I'm going with it.

That said, it she says she wants to have someone join us, I'm all for it!smile

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