It had been a few long couple weeks of holidays, family, job hunting, and over all just being busy. After learning Jackie had landed a better job, we needed to celebrate with a date night.
While I was giving the babysitter the last of the details for the kids bedtime, Jackie came out of the room in a sexy outfit. Her sweater was cut low showing off a surprising amount of cleavage. The skirt she picked out was the shortest I’d seen her wear in a long time. Her amazing legs were protected from the cool air by a pair of thigh high socks and black boots.
My eyes practically fell out of my head taking in her beauty. I’m not sure what the babysitter thought, but I’m she she got an eyeful as well (maybe she enjoyed the sight too). “Ready?” She asked me as I stared. “Sure am” I answered snapping out of my trace, and after saying goodnight to the kids I guided her toward the door with my hand on her ass. Being a gentleman I opened the door of the car for her. Sliding into her seat she made sure to flash the mesh panties she’d chosen to wear. She smiled as my gaze moved up her body taking in everything she’d put together. I am a lucky man.
I complimented her on how sexy she looked that evening. She reached over stroked my thigh and growing bulge. “I’m not the only one looking sexy tonight.” Dinner was going to be filled with a lot tension.
We arrived and started with cocktails. As the alcohol set it we couldn’t keep our hands to ourselves under the table. We took turns discretely running our hands along each other’s legs, slowly teasing higher and higher.
Between the main course and dessert I excused myself to the bathroom. In the stall, I found the evidence of what Jackie was doing to me. I pulled out my phone and snapped a picture of the bulge and pre-cum leaking thru my boxer briefs and messaged it to Jackie.
As I returned to the table, Jackie leaned in and whispered into my ear, “holy shit honey, I thought I was the only one who was that wet” She guided my hand up her skirt until I reached her mesh panties. I could feel her juices had already soaked them. My fingers traced her smooth labia and she leaned in again to moan softly into my ear. “Mmmmmhmmmm, I need to excuse myself…” walking away she made sure to sway her hips to keep my attention.
Dessert and the last round of drinks arrived. Jackie returned with a smirk on her face. Sitting down she laid her wet panties on my leg and smiled. I slid them into my pocket and then my fingers explored her now exposed pussy. As she took a bite of the dessert I slid my fingers down her slippery slit and teased her clit. Jackie moaned aloud as I did.
“It’s really good isn’t it?” Our waitress chimed in from behind us.
“You have no idea!” Jackie excitedly answered, getting caught being sexy a second time tonight.
We finished our meal and paid our check without any more surprise interruptions. When we arrived at the car I pressed her against the side of the car and kissed her with passion and intensity. She broke away and said we should be making our way home. This time as I opened the door for her, I got a view of her beautiful pussy and she gave herself a little tease. “There’s more dessert at home” and she licked her fingers.
She hiked her skirt up on the way home and continued to tease herself. I could hear the wet smack of her fingers against her pussy as I drove. As we arrived home, I quickly paid and excused the babysitter while Jackie made her way to the bedroom.
Opening the bedroom door, I was greeted to an amazing site. My sex goddess laying on the bed in just a see thru mesh bra that matched her panties from earlier and thigh highs fingering herself. Stripping down, I leaned down to kiss her. She stopped playing with her pussy and reached over to play with my smooth balls and rub my leaking tip with her thumb. It was my turn to moan as I kissed her.
Sitting up, I reached behind her to release her bra and take in her beautiful breasts in their full glory. Leaning in, I kissed, licked, and nibbled each wonderful mound while she continued to stroke my rock hard dick.
Not wanting to cum from stroking alone, I playfully pushed her back on to the bed. Laid out before me, I was ready for second dessert, but first I knew she would want to be filled too. I grabbed her biggest dildo from the nightstand. A thick, 10″ pink one with big balls perfect for controlling. “Oh yes, that’s going to feel great….mmmmmmmm” she trailed off as I took her labia in between my lips.
I licked and tease her pussy all over. Her taste was amazing. I wanted to take it all in. Pushing my tongue into her she moaned and pulled my head closer to her. Pulling back it was time to fill her. I pushed the tip of the dildo against her opening as I licked her clit. She pulled me in more. Inch by inch the faux member made its way into her soaked pussy. She growled as the fake balls pressed against her ass cheeks. While I continued my attention on her clit with my tongue I moved down so my chest held the dildo in her.
She pushed against the headboard and started fucking my face. Writhing and twisting to get everything right. She moaned and growled louder as the sensations grew. I grabbed the testicles of the dildo to fuck her harder with it. As I pushed it in, my knuckles pushed against her asshole slick with her juices and I heard her groan, “Mmmmhmmm…yes please….” She pushed against the headboard again wanting more pressure against the forbidden zone. She ground harder and harder into my face and knuckles. I decided to go for more.
Grabbing the lube from our toy box I applied it to her waiting ass. Rubbing my thumb against her pink rose she moaned louder then ever. I laid down again and resumed my attention on her clit. She was going wild with all the sensations. I rubbed and pressed my thumb against her tightest hole until it opened up and slid in with a gasp of pleasure.
She bucked and fucked my thumb in her ass as I sucked her clit. Feeling the building climax I took my free hand, pulled back on her trimmed mound to fully expose her pearl to my tongue. She screamed louder and louder as she got closer to cumming. Circling my thumb in her ass, she pulled on her hard nipples and finally released all the built up tension. She clamped her cotton covered thighs around my head and screamed at he top of her lungs. I kept going as she quivered and twisted around me. After what seemed like minutes. She finally tapped out and needed a break.
I went to wash up and came back to find her laying in bed teasing herself with her dildo. I laid beside her and she put her hands on my cock. As she relaxed I asked her how her first DP orgasm was. “Really good! So many sensations!”
Finally it was my turn. We decided on the position and I pulled her to the side of the bed. I put a pillow under her ass. I teased my cock up and down her slit before sliding in. She was still so tight from her orgasm. I picked up the pace knowing I wasn’t going to last long (laying on the bed with my cock against the soft sheets was a lot build up).
As I pushed into her, her natural D cups bounced with the waves. “Oh fuck, your cock feels so much better than the dildo” The sound of our bodies colliding and dirty talk filled the room. Within minutes it was too much and I needed to cum. “Where do you want my load?” I growled. “Cum in my tight pussy! I want it inside me!” With that I pressed so deep into her I felt the lube on her ass against my balls and unloaded. With every twitch and throb, rope after pent up rope shot into her until I was spent.
I pulled out slowly and admired her well used pussy and ass as my cum started leaking out. She cupped her hand over herself and we got up to cleaned ourselves. Exhausted we passed out. When I woke up, I knew we had a new story to share.
Source: reddit.com/r/gonewildstories/comments/rlja62/long_overdue_date_night_leads_to_dp_mf