It had been a few weeks since I’d seen Jessie, my favorite forbidden fruit. I call her that because she is younger in her 20’s and I am…not. I think she is trying to get serious with a boyfriend. I”m on the DL for her. She’s a hot olive-skinned mediterranean type with an amazing body. Jessie is athletic and yet curvy in the best feminine ways. She is athletic, has a little sassy side to her but likes that I am a bit older and can play the authority card when we are together. I told her that any sassy talk in my direction comes with a price and to save it for her younger boyfriends. She has the most voracious appetite for sexy playtime and her oral skills are second to none. We’d been fwb for about a year and a half. I don’t know how but we just have the same tastes and same appetite when it comes to sex. I don’t have to ask about things because every time I have asked she already knows that she wants that and would like to try it if she hasn’t. I spent several months picking her brain on various aspects, positions, and mental side effects of certain types of sexual interaction. a boyfriend had taught her about anal and some cum play so to find out that she liked ass play was a bonus surprise. We live a solid drive apart but met while working together a couple years at a non-profit. Texting, sexting, and some hot skype sessions took the edge off fairly regularly, but in a way also made things difficult by keeping the visual stimulation going.
Two or three attempts at a meeting to play were thwarted by work and other commitments. I had to take a trip north for a long weekend and as luck would have it Jessie had a day off of work as well. with reliefe in sight I booked a room and crossed my fingers.
My blue balls were set to explode with a multiple day load that I had been carefully saving to feed this hungry 20-something babe. In a gentlemanly attempt to return the favor of many amazing oral treatments, I had been faithfully avoiding coffee, reducing my red meat consumption, and pounding pineapples, pineapple juice and green smoothies as often as possible. I let her know that I was sweetening the load in any way possible and had every intent to feed her everything I had saved up.
So I hit the road with a smile on my face and drove a couple hours to the meet-up point a little over halfway to my destination. It was hard not to get ahead of myself mentally as every anticipatory thought gave me the start of hard wood inside the boxers I wore for the sake of easy public space access….just in case. I knew she liked that.
We met in a parking structure near the hotel. My first view of her put a huge smile on my face and hers as well. Real life views are so nice after an extended absence. Her outfit was casual but looked very hot- a dark v neck tee and a short mini-skirt in a complementary pattern that really highlighted her awesome legs and ass. Jessie has a thick mane of dark hair with highlights, big brown eyes and a big bright smile that will melt any bad mood away. I greeted her with a short hug and an ass grab and trying to play it cool asked where she wanted to eat.
Thank goodness she said she wanted to just go play. As I walked to the car I snagged a perfect kiss. and more hand up the skirt to grip that perfect ass. Once inside the vehicle it was an instantaneous make-out welcome that started out private and included plenty of ass, tit and hardening cock grabbling through our clothes. Sure enough, a garage janitor soon managed to maneuver himself into viewing angle and I toned it down a bit. Especially since I wanted to stop for a quick beverage and couldn’t walk through a store with a raging hard-on. I anticipated a thirst inducing afternoon.
We checked in after a maddeningly slow desk attendant finished her conversation with a maintenance staff member. The whole time I was thinking of what was up that short skirt and wet kisses al over me from those plump sexy lips.
As soon as we got to the room Jessie wanted to jump all over the bed and wrestle, but I was going to take my time and enjoy every phase of this happy reunion.
I gave her a long hard hug wrapping her up tightly , and reaching back to grab her ass with both hands strongly controlling where she could move. I pulled her against my hardening bulge and pulled her full breasts against me.
I assumed the controlling role and sat in an armchair with my drink next to me and told her to stand in front of me and spin around so I could admire all angles. She was looking so good, tanned from summer and hair flowing. I had her remove her top to reveal that she was wearing the bra I had requested: a subtle pale lacy thing that you could partially see through to view her nipples.
I had her twirl around and bend over so I could enjoy the sweet view of her cleavage before ordering her to bend over and show me her ass. Pale lace barely covered her neatly trimmed pussy and her browned ass cheeks swallowed the back of her lacy things easily. I couldn’t wait to eat that ass as I peeled her skirt down to the floor and she stepped out of it.
She knelt between my legs to finally free my hardness, eagerly unzipping my shorts and freeing my cock through the fly on the boxers. She began kissing my cock and caressing and kissing my thighs, cock and balls underneath …damn it felt like heaven. I had her remove my shorts and boxers before her drool soaked them adn let her go to town on my engorged dick. She really liked the shape of my circumcised head and knew just how to make it swell up like a giant mushroom cap. I loved the way her mouth was perfectly wet, perfectly soft with not too much suction. She never scraped inadverdantly and always went as deep as she could. I was the first guy to feed her my cum and make her swallow it , so it was like we had a little secret. Only one other previous lover I had would willingly suck me dry and I think Jessie was better even though she was less experienced.
I grabbed and softly swatted her ass as she bent over me teasing her of things to come.. and then so I could keep it under control I had her straddle my lap with her legs wide so I could play with her barely covered tits. They were the perfect size D and had the nipples set sort of lower and sort of swinging away from each others full curve to create a great space for a face to rest and nuzzle the inner fullness of each one. I kneaded then through her flimsy bra adn then unhooked her bra. As it fell away I feasted on those nipples to her delight and she ground that barely there thong against my package, clearly getting soaked.
SOon she was begging me to fuck her but I wasn’t done reacquainting myself with her full form. I had her stand and bend over so I could peel her thong out and down to the floor while enjoying the musky scent of excited pussy. My mouth was watering as I viewed the swelling lips around her wet hle and that tight little ass hole. In one of previous hookups I had eaten her ass during 69 and it was delicious to anticipate. She had reveled to me that a boyfriend had already introduced her to it but I was willing to be the second explorer to land if I could have access whenever I wanted. She had also revealed an enjoyment for anal play and anal sex in the past so my mind raced with memories as well and I wanted to torture her by making her wait for the cock.
As I tossed her onto the bed I alerted her that I had packed a little surprise for her and she liked that. I instructed her to sit and close her yese while I blindfolded her.
I unpacked my first surprise ..some soft restraints with which I bound her hands together above her head and tied to a bed-sheet that I had fashioned into a controlling rope.
I then went to kneel at her feet and dripped lubricant onto her breasts and nipples. She gasped with a start and I started kneading her gorgeous body with lube. I love the outside curve of her breasts and spent a lot of time massaging her chest shoulder and arms just to make her suffer before enjoying those sweet full tits. I pinched the nipples and gave them a slap before heading south to her abs and thighs, avoiding the most sensitive zones for now. I wanted her to suffer the way I had…waiting for a taste for weeks. Then I went to work on her hungry mouth, kissing forcefully, nibbling at her neck and ears and forcing her mouth open to plunge my tongue into her . Her taste was again familiar. I bent over her face from above her head, pulling her arms up and back. Then I kissed her mouth and face and chest from above, secured her sheet “rope” with my legs before groping at each heaving tit. she gasped and moaned and asked me to suck her tits, to feed her my cock…all in good time, Dear Jessie, all in good time.
I admonished her for trying to get her hands free adn then came phase 3 of the surprise: a gentle whipping with a cat-o-nine tail whip. I had not used one on any of my previous lovers and she had never either so it was a complete surprise to her feeling that first gentle whack as I brushed it across her lower ribs under her left tit. I adminished her more for trying to ruin her surprise by loosening her hands and I resecured her hands , her blindfold and whipped her again on the other side. Again this time on her left thigh, then again on the right thigh. I wanted her to be anticipating but wondering where the next blow would land and it was right across her right breast and nipple. It was not hard at all but a surprise in the dark. I wanted her getting wetter and wetter and kept the blows coming between hard kisses, tugs on the hand rope and hard kisses and sucks on those gorgeous tits.
I was having a hard time hoilding back my self and she was begging to be fucked. I told her to shut up and take it or she’d be sorry. That was the penatly for being unavailable for so many weeks.
Next I spread her legs and scoped out her waiting pussy with my nose, then my lips, gently. tentatively.She was wet as hell and I was eager to get in there but first I wanted to eat pussy and I started with licks from my tip of my tongue and then the flat of my tongue on her clit. As she begged for more I started sucking the clit softly and pulling on her pussy lips with my mouth. I pushed her legs up to her chest and dove in when I couldnt take it any more licking the full length of her pussy lips to clit sucking it then going back down with lip kisses and sucks. I let my tongue wander down to her asshole and told her that I wanted to fuck her ass before givng her what her pussy wanted so badly. She wimpered and protested but to no avail. I took what I wanted when I wanted it .
FInally I put a rubber on my cock and teased her asshole with the head of my cock and with lube. I wanted that ass sphincter tight around my cock and was gently but steady, opening her legs and making sure she was lubed well. I also wanted to eat her pussy before that happened and took my chance after purposely teasing her entire ass and pussy area with tongue mouth fingers and hands.. Shoving my cock to full depth in her ass was fantastic and I stopped to enjoy the sensation of being fully engulfed. so warm adn tight around t he base of my cock she was . I gave her small slow motions so she could feel my shape deep inside her. after flipping her over and making her take my cock in the yoga position known as ” childs pose” resting on her chest and thighs with her ass in the air.
I cleaned off my cock from ass lube and put on a new rubber. I wmade her suck me with bound hands and then arranged her on top of me so that she couuld do some damn work. As she settled her pusssy down onto my cock I told her she was going to work and grind me until she came. I man-handled each tit very firmly with my hands as she started to grind, slowly at first and then faster, as her breath got ragged. My sucking caused her nipples to leak out a sweet milky substance which was fantastic and then I let her mouth hungrily wrestle with mine as I felt the head of my cock rubbing her rough g spot areas.
Jessie did not disappoint. Although she managed to pull her blindfold off and free her hands as she rode me, she came loudly and hard. She panting her pleasure into my ear with her whispery gaspy “fuck-voice” and I could feel her pussy clenching tightly around me in wave after wave as she shuddered above me. Her tits swung madly as she finished getting to that point of no return and I those weeks of waiting melted away. I love making my partners cum hard and I love it when they don’t hold back. I think it’s the sexiest thing in the worl hearing and watching a woman orgasm while you are inside her and love vocal women. Porn never does that justice which is why I usually only get off to amateur vids or the real deal. Fake “pleasure” noises ” have me changing the movie before it even starts.
I told her my turn was next adn I loved fucking her missionary with her legs held up against her chect by my arms. I liked kneading her tots mercilessly while slowly giving her every inch of my cock and then sliding it all the way out again. that moment her lips would envelop my cock head and the nthe shaft was my favorite fucking sensation and I made sure to enjoy it. She was joyously wet and slippery and begged me to cum inside her.
I grabbed her by the neck firmly and reminded her that I cum when I want to – not when she tells me to. I told her that she would pay if she kept up withthe sass and playfully slapped her face and tits until she said OK, OK Ill be good.
Jessie falls into a submissive role so easily and it took me a little bit to realize that she really enjoys it, wants it-wants that authority telling her not to get out of line and it’s a fun role play.
Eventually I just wanted to cum into her hot body but wanted to be sucked dry. I flipped onto my back next to her and told her it was time to make me cum. She was desperate to have it at this point and had that sweaty forehead sweaty edges of her hairilne and that depserate look to her eyes as I took off my rubber and wiped off the lube so she could suck a pure dick. She again did not disappoint, using a combination of her gentle hands, wet loose lips, and active tongue. I had placee one of her hands under my nutsack, she had one around my wet shaft and was going up and down like a pro. She was taking me full depth when her hand wasn’t on my shaft and we both pushed hard to get all the way into her throat with the gagging causng more drool to come out which felt soooo good. When I was on the edge I let her know and told her don’t you dare spill a drop as she increased her hand speed on my shaft. I felt as if I was hit by a 10000 volt shock through my body as I came in her mouth after weeks of waiting. My whole body convulsed, hands gripping the sheets and flailing, pounding against the bed as she suck and sucked and I pumed wave after wave of spurting ropes down her throat. Even after I stopped pumping cum out she kept sucking and licking me clean as my my abs spasmed and lifted my head off the bed in waves of relief.When she finally released my softening cock I was spent and she had that grin going. that one that says she knows she did a good job getting me off.
We laid one on top of the other sweaty body against sweaty body, then dozed briefly before she got me aroused again and I went hard at session #2. It felt more relaxed, more easy going. She knew I wanted to leave drained and knew I wanted her to leave with legs like noodles, sore nipples and a little bit of fatigue in that pussy. She confirmed with a smile that my cum tasted differently than the last time she swallowed me, less bitter in the start and less salty in the finish. She is currently the only lover I have who swallows every drop of hot jizz that I pump out and it is fun for her, I think, to know that this tap is all hers. I think we reached our objectives, and parted ways until the next time.
It was a very relaxed family trip with none of the angst I get from not having a release for 2-3 days. I was pleasantly spent and I know I am a much better person to all when I feel that way.
I don’t know how long we will be able to keep this up but who knows maybe she’ll get a bf with a dirty mind and we can get some threesome fun going. I know that would top it all.
Source: reddit.com/r/gonewildstories/comments/7t1het/hot_meetup_on_the_way_to_a_mfamily_trip_long