From GoneMild to GoneWild. [m/f] Casual, Anal | 2016

Lynn and I met on a hookup site several years ago as both of us needed rebound sex. We were both coming out of long relationship and just needed companionship and the occasional booty call. Lynn was only free a couple times a month as she worked all the time doing double shifts. So at the beginning, things were slow to progress and get to know each other. She is a cute little Asian number who is in her 30's, little on the curvy side and simple in her needs and desires. About the only thing she is consistent on is her love of massages, foreplay and being "lazy" during sex. AKA, wants me to do all the work.

Lynn seems to like just about everything so long as she just gets to lie there or be in a comfortable position. I love to be in control to a willing and enthusiastic sex partner, but training Lynn to be more energetic was tiring and a hassle. She was scared to try anything new or potentially painful. Anal was absolutely out of the question and so adamant about it that I didn't even bring it up again. A very bad experience left her to mentally write it off as never-again.
Things between us stayed vanilla (yet good) until she and I hit that peak phase when it was becoming boring and routine. Lynn and I stopped our bootycall hook ups for a while and only hooked up once more before it was a mutual thing to let things just phase out.

One evening month later, she sent me a text asking if I was busy. It had been nearly 3 months at this point and I had moved on but still not in a relationship. I wasn't particularity interested in vanilla sex with her anymore so I threw a hail-mary and told her on one condition. "you're going to have to obey me and my desires all night. Can't say no at all." knowing full well she would chicken out. When I saw she wasn't replying, I felt a little guilty. I followed up with, "You'll get 6 orgasms, you know I'm good for it". Still no reply and at this point, I was getting horny... I almost gave up on her when I got the reply text, "ETA 10mins" and she lived 45 minutes away. Hahahah, apparently she was revved up!

Lynn wasted no time in stripping down and stood in my bedroom waiting for orders. I was dumbstruck at how into it she seemed. I introduced a very reluctant Lynn to 2 of my favorite sex acts... complete obedience and anal sex. The complete obedience was surprisingly harder for her to accept over her willingness to do anal as she was so against it at the beginning. She would later tell me that she trusted me to be gentle and to make sure to go easy on her. That first evening she did anal with me was far better than expected. She didn't cum from it but was telling me constantly how good it felt. It was a new experience for her and she "sort of liked it". Not messy at all like she thought nor did it hurt past that first few moments.

I gave her multiple vaginal and clitoral orgasms as promised and she was soon passed out after an exhaustive evenings entertainment. Lynn woke up next to me about 2 in the morning completely horny and revved up once again. She was clearly in the mood to try anal sex once more but the mind was willing, yet the flesh was weak. She was obviously sore and the pain was too much for her to try again so soon afterward. But she had what I like to call, "the anal itch" the inner desire to do it again to satisfy that scratch only a cock can do.

Lynn was calling me again by the next weekend and clearly had an agenda. She arrived, had a quick massage and was soon wet between her legs from anticipation. She played coy of course, telling me to just fuck her wherever, but I wanted her to say it. I toyed with her pussy a bit as my fingers teased her soaked lips. I probed in and out of her, whispering words and nibbling her ear to increase the foreplay. Finally she came out and said it, "please... stick it in my butt." and she covered her face from embarrassment.

I wasted no time in scooting her over the edge of the bed. It's the perfect height for her waist as she can bend over and her feet can touch the floor comfortably. I lubed up her ass with Relax© desensitizing anal lube and jacket'ed up. Those first few moments are always slow and steady and Lynn was breathing steady as the first hurdle was passed. I waited patiently for her to get used to my size and with surgeon precision... I slowly slid out letting her feel my girth and pressure. She gasped and moaned with both pain and pleasure but was soon giving in to the moment. In a surprisingly quick amount of time, she was matching my slow and steady piston rhythm with a complimentary thrust back into me of her own.

Lynn was soon lost in the moment and started moaning in pleasure as I increased speed and thrust. She was groaning as if my cock was the release she needed from years of pent up frustration. I honestly couldn't believe that she was that into the moment. This woman barely moved to my thrusts into her pussy but here she was bucking me like a bronco in heat. She came moments latter and I was honestly just getting started. But she didn't stop... she paused for a quick moment to bask in the glow but was soon matching my pelvic thrusts again as we fucked her into another orgasm bigger than the last.

The transition from lazy bootycall to anal sex crazed fuck toy was like flicking on a switch. I have lots of experience with kinky sex partner's, many of whom were into anal. But I had never seen a transition like this before. Lynn was seriously into it and there was no vaginal or clitoral stimulation except for the edge of the bed. I was becoming lost in the moment too as fucking her ass was amazingly tight yet felt so good. I couldn't count how long we were going at it but it was a good 10 minutes at least. She had cum 5 times.. each as big as the first if not bigger and I had finally cum.

We cleaned up, took a shower and basked in the afterglow for a while. We cuddled, talked for a bit about our week and finally got to talking about the amazing sex we just had. She seemed eager and scared about something. When I inquired, she finally told me the full story. Typically ex was too forceful, didn't know what he was doing and caused a LOT of pain and discomfort. But was interesting was she was interested but scared to ever try again. What was also news was apparently, she had a female co-worker than she's close with share some intimate details of her sex life. The topic of anal had come up and how it was a regular part of her life now. The co-worker had made a bet with Lynn that if she tried it again and liked it, she had to share the details the next day with her.

As I was getting horny again, I asked for round two and she happily agreed. This time we tried doggystyle anal... too uncomfortable for both of us. Spooning anal with her leg up and me sliding in from the side... again no luck due to the angle and my size. We tried several more positions with minimal luck until we settled on a yoga pose where she bent over completely at the waist and grabbed her spread ankles. With her back nestled up to the side of my bed and her ass presented perfectly to the height of my cock, I plunged in with minimal effort.

Her moans were music to my ears as she clearly had no pain or discomfort during the start of round 2. She was fastly approaching an orgasm when I had an idea. I slapped her ass checks fairly hard as I demanded her not to cum. I could tell she was obeying because of the whimpered moans followed by guttural gasps of pleasure. I can't tell you how long we had been going at it but it wasn't long. Soon I stepped up my trusts and my pelvic thrusts were slapping hard into her ass cheeks. My cock was being shoved the full length of my shaft into her cave of wonders and she lost control. She was attempting to speak english but all's that came out of her mouth was "Yeea... uck... ..eah... my.... ass.... uuuuughh... ard... yeah.... pound... UHHHHH!!"

Lynn had lost muscle control of her legs from being bent over for so long. Her hips and ass were slowly falling back down to resemble something of a completely bent over gym squat only my hands were now holding her legs and thighs up near her ass. I was still pounding away with near maximum effort. Lynn was beyond coherent at this point. Crossing between grunts, mumbles and the occasional words moaned in ecstasy. I command her, "ARRRGHH!! Now Cum for me!!!" and she does. A long stream of guttural groans escape her mouth as she gets the release she craves. I explode in a series of body rocking spasms as cum in her ass.

Over the course of the next few minutes, I continue my wind-down of thrusts into her now loose anal hole and she has all but slumped into the bed using her back for support. I'm completely spent and Lynn is obviously ready to collapse as well. I pull out and her legs involuntarily shake and quiver with the effort of having to support her own weight again. With the remaining strength left in her, she forces her upper body back into the bed and just rests still bent over at the waist. Through panting and labored breath, Lynn gasps out, "that.. was... the best... orgasm.. .... (weeze) ohh .... my .. god. look at the floor." Below her was puddle of cum from when she squirted.

Prolog:

Lynn and I are still together as fuck buddies and she frequents about 2-3 times a month. Not as often as we'd like but our schedules suck. She has since accepted the fact that she loves anal sex as much as normal sex. Still embarrassed to ask for it and talk about it in person, but she at least can now openly text about her love for it. Her dirty talk has made major headway as she can now beg and plead for me to go harder/faster/slower while I'm up her anal cavity. She's "my anal slut" now (her words she's asked me to call her) and her and her co-worker are inseparable now. Their shared experience and love of butt loving has made them a horny tag team of getting themselves in the mood for more and more.

=) Thanks for reading.