First Time Anal Sex: Mile High Club!
I guess you might call me the typical sexually frustrated divorced housewife. My fascination with anal sex movies can be blamed directly on my ex-husband who couldn’t satisfy my sexual needs but, he sure could win his fucking fantasy football league every damn season! While he jizzed all over the best match ups every Sunday, I decided to live my life through the internet. His weekly fantasy football fumble (of me) definitely opened up a new world which quickly became a secret life and outright obsession for me. While he watched nine or ten games at once, I withdrew to my study and closed the door. I couldn’t fucking stand the hootin’ and hollerin’ at the players on TV while I tried to relax. I never understood fighting with the TV, they can’t fucking hear you no matter how much you yell. Idiot! Little did I know that my sexual frustration would lead this anal virgin to join the First Time Anal Sex “Mile High Club!”
I poured myself a glass of wine and always brought the bottle as I sought the solace and tranquility of my study. I have a very large monitor and surround sound setup, so my internet experience takes browsing takes a whole new level. At first, I sought out more feminine topics to pass the time such as shopping. It didn’t take me long to figure out that I could masturbate my (at least some) sexual tension away during the football games. I surfed some of the more soft-core websites and more traditional porn movie sites. I quickly became bored all with the fake mainstream shit out there and turned to more kinky topics such as anal sex and some mild kink like lesbian strap-on sex thrown in for good measure.
About halfway through the football season. I happened upon this awesome site where I could watch anal sex movies and read all kind of kinky anal erotica. After reading some of these naughty stories, my mind was racing with something I had never ever considered; anal sex! I hadn’t had a decent pussy fuck for several years and the thought of a hard cock, or strap-on buried deep in my ass had never even been on my radar. That just shows how sexually frustrated I was at that point of my life! My ex-husband chose football over me and that’s totally fine. He can has his football tight ends while I let others fuck my tight end! 😉
While I was nervous to divulge my secret anal sex fantasies to anyone, I figured I could remain anonymous by purchasing premium porn website subscriptions and chatting discreetly with live webcam models from time to time. This brought some initial satisfaction as I was able to experiment in the privacy of my own home office study. I was so thankful to all the kind women online that offered their suggestion for my first anal toys, lube, etc. When my first sex toy package arrived, I almost broke my leg running into my study tripping on my favorite area rug. Fuck, I was so horny and just couldn’t wait until I felt the self-induced pleasure just moments away!
Upon opening the box, I discovered and small dildo and a beautiful piece of artwork that just so happened to double as a butt plug. As I lubed up the small anal dildo it was only a matter of time before I took my own anal virginity. Just as I was teasing my asshole, the phone rang just as I was about to insert it into my waiting virgin ass. So much for any butt sex now. It was my corporate office on the west coast informing me they were restructuring the company which required me to travel to Los Angeles first thing Monday. What shitty timing! Now, my mind was totally off anal sex and raced toward what the restructure was going to bring come Monday.
The weekend proceeded to suck and I was so edgy that I didn’t even want to be around myself. Monday morning came and the driver whisked me to the airport. Luckily, I was upgraded to First Class which made the cross country flight a little more bearable. Even though it was a business trip, I ordered a stiff Bloody Mary and then proceeded to spill it all over myself. I was so fucking sexually frustrated that I wanted to masturbate right then and there! I was pissed that I didn’t bring my sex toys for fear security would expose my naughty side for the whole world to see. The flight attendant told me not to worry that she would help me cleanup once the plane reached cruising altitude.
Once our flight had reached the appropriate altitude, the flight attendant approached and asked me; “Why are you so distressed?” I informed her that I had a big corporate restructure meeting all week and that I hadn’t been laid in several months as well! Shocked, the flight attendant instructed me to follow her to the mid plane lavatory. I was surprised she didn’t want to stay in First Class but, quickly discovered this bathroom was slightly larger to accommodate handicapped passengers. “Now, stay here,” she commanded as she departed to the back of the plane for a few minutes.
When the flight attendant Elaine returned she held a bag in her hand and told me to go inside and give her the blouse I had just spilled Bloody Mary all over. I immediately started to apologize for my lack of sex remark and she put the index finger to her mouth as to say, think nothing of it. “We all go through dry spells my dear,” Elaine comforted. Dry? Hell, my MILF Pussy had been in a a dessert-like drought for several years!
Elaine was an extremely attractive woman of Asian descent. Well built with perfect sized breasts and shapely legs. You could just tell that she was a super nice person even when she wasn’t paid to take care of messy airline passengers such as myself. “Now, go inside and give me your top. While I clean the stain, please stay in the lavatory until I return. I will knock three times to signal it is me.” Before Elaine left she handed me the bag and told me this should make the trip go by a little faster and to just relax and enjoy the flight. Her final message before departing had me intrigued, “I believe the contents of this bag should allow a creative remedy for your issue.”
Elaine bid farewell with a seductive wink as I locked the bathroom door for several minutes. I felt naked yet aroused standing there in just my bra and mid-length skirt. Almost immediately I could feel myself getting wet between my legs. I looked back at the lock to ensure that it was latched and then my curiosity finally got the best of me. Slowly I oped the bag only to discover a measly hairbrush and one of those battery powered toothbrushes. “What the Fuck,” I thought to myself as my pussy continued to moisten. Then, I replayed Elaine’s words carefully in my mind. Then it hit me, “Creative remedy for your issue.” Well, my issue was being so fucking horny from total lack of sex.
I removed the hairbrush and noticed that the end looked surprisingly like a dildo. Next, I took the toothbrush out and clicked the lever to the “on” position. Wow, this little fucker really gets with it I thought to myself. Suddenly, I put one and one together and had my “Aha” moment. Not wanting to waste any more time, I took the hairbrush end and ran it under the hot water before hiking up my skirt and plowing it inside my dripping pussy. Fuck, it felt so good having something nice, warm and hard inside my cunt! I pumped my pussy good but, needed more stimulation. That’s where the battery powered toothbrush came in. Elaine was a horny little slut in her own right! I turned that little sucker on and held the end directly on my clit.
My knees buckled and I believe I saw stars not known to man as the vibrations from the toothbrush transferred into pure pleasure through my clit to the rest of my body. I looked at myself in the mirror and saw no shame in what I was doing at all. I was so fucking horny and Elaine was the just the friend I needed at this point in my life. I firmly believe in fate and I guess she could see in my eyes just how desperate and horny I really was! I couldn’t believe just how good the combination of hairbrush in my ass and a battery powered toothbrush was making me feel. I was fucking my pussy vigorously and could smell the womanly fluid that was dripping down my legs now.
Suddenly, another sexual light bulb went off. Yes, this as was moment where I took my own anal virginity. There was no question that the end of the hairbrush was properly lubricated with my own pussy juice. With little hesitation, I withdrew the hairbrush and pressed the well lubed end toward my awaiting and eager asshole. I was so ready and becoming relaxed that it only took a slight push to enter my first time fucked brown eye. Damn, it felt so fucking amazing having a hairbrush dildo shoved into such a dirty place. It only took a few milliseconds for me to find the perfect balance of anal penetration and clitoral stimulation. Having masturbated hen I watch anal sex on a regular basis, I know my body pretty well. Although I had never had a dildo in my ass before, I knew I was only a few strokes and clit vibrations away from a knee buckling orgasm.
In the heat of the moment, I had lost all track of time. I knew that I better focus on cumming as I was so close. I lost focus momentarily as I heard the lavatory door knock code of three times signaling the return of my sexy flight attendant, Elaine. Just the thought of her ramming the dildo into my tight ass was enough to push me over the edge. I did my best to muffle my orgasmic scream but, was more vocal than intended. It all happened so fast as shock waves were sent from my cit and my ass gripped tightly, clenching around the hairbrush dildo. Believe me, there is really no way to describe the feeling! As I withdrew the hairbrush from my freshly fucked ass, I couldn’t help but smile proudly of my fantasy turned reality which was of the same porn star worthy caliber of the anal sex movies I had ever seen on my favorite Roku porn channel.
I quickly pulled my skirt back into place and washed off the hairbrush. The door then knocked three more times. Sheepishly, I opened the door as Elaine gave me my blouse back in nearly perfect condition. “So, have you calmed your nerves any, hun?” Elaine asked. “You have no idea (actually, she probably did) how much better I feel now. Thank you so much for getting the stain out of my blouse.” I put my blouse back on and placed the hairbrush and back into Elaine’s bag. As I exited the lavatory, it seemed like I had been in there for over an hour. Actually it was less than five minutes which isn’t much time considering I lost my anal virginity while joining the Anal Sex “Mile High Club!”
Elaine met me with a smile as I handed her back her bag of creative pleasure. We both walked back to First Class where I was more than happy to recline my seat and take a nap for the remainder of the flight. As we prepared for landing, I felt a soft yet firm hand on my shoulder asking me to put my seat back to the upright and locked position. Elaine made eye contact with me and I’ve never wanted to kiss anyone so badly in my life. The pilot then instructed the flight attendants to take their seats for landing. I just about passed out as there was Elaine buckled in and brushing her hair with the hairbrush that had just been in my pussy and ass! How fucking dirty was that, I thought as Elaine looked up and gave me a sensual smile that had my pussy getting moist again.
As the plane touched down, the sexual chemistry between Elaine and I was obvious. I had never been with a woman before either but, sure wouldn’t have to be asked twice to let Elaine take my lesbian virginity! Indirectly, she had already had a hand (or should I say hairbrush) in my First Time Anal Sex Mile High Club fuck. As the gateway made contact with the plane, I knew I was in for long week at the corporate office. Luckily, I would have memories of Elaine’s kindness to get me through everything, including a call to my divorce attorney once I checked into my hotel. As I exited the plane, Elaine gave me a thank you for flying with us handshake. Elaine casually whispered in my ear that she wrote her telephone number and email address in the hem of my blouse and thanked me for flying “her” friendly skies one last time. As I walked up toward the gate, I gasped and said out loud, “Oh shit, I forgot to rinse off the fucking toothbrush!” 😉