This is another story I am telling based on a prompt. This promt was someone sent me a picture of two pornstars with one taking a cock deep in her ass and the other looking on. The text simply read “watching my girlfriend do anal”. I cant post it here but.. it was inspiring. I opted to end the story at the moment the picture was taken to allow the reader to place their own context where the story goes. The person who requested this story has since deleted their account but i want to thank them for their request. As always comments or PMs are super appreciated.
My Anal friend.
Our sex life was great. My boyfriend and I had run the gamut on exotic and interesting styles of play. That is until we hit that barrier. One day I found him sitting at his computer a nice video of a beautiful larger blond woman coaxing and purring at her partner to take her in the ass. He was transfixed on the screen. I had never seen him jerking off that hard. I know his type of woman so I don’t think it was her that was turning him on so. It was that idea. The proverbial Mount Everest of orifices. My man wanted to fuck me in the ass. The thought itself was such a turn on. I left him to his jerk off session but the thought remained in my head. That night before bed I breached the subject.
“I saw what you were looking at today on your computer” I teased.
“Oh yeah?, I don’t know why but i was in the mood for that” he confidently replied.
“I don’t think i have ever seen you so… voracious and I think I know why. Why dont you join me in the shower and I’ll show you.”
I wiggled my ass as I crawled out of bed and headed to the shower. He tripped over himself following close after.
I love shower sex. The steam and heat are such a turn on. The excuse to lather each other up and hold each others bodies pressed against one another just makes me dewy. We kissed and shared each other’s tongues. I stroked his cock with some of the soap so that it was slick with precum as he rubbed and fingered my pussy in the same way. When he was fully erect, slippery, and ready. I pulled away from him, threw him the most devilous mischievous smile I had in my arsenal, and turned around placing my hand on the wall by the shower faucet. I pushed my ass toward him placing the full length of his shaft right across my crack. I turned my head to him.
“THIS is why you were so voracious. You want to fuck me in the ass. Well… DO IT”
He groaned as he grabbed my hips.
“I love you” he sighed.
Searing hot pain. Oh my fucking god. This is NOT going to work. He got just the tip of the head of his cock in before I pulled away almost crying. I was shaking and panting. All sexiness had fallen away and all i could think about was how much that hurt. A little pain is nice but that was too painful. He apologized profusely. He kissed me and nursed his erection down to a dull roar. He was such a caring lover and I felt really bad about it. But I don’t know how women do that. He was so sweet about it and after the shower I sucked him off with every bit of the enthusiasm he had jerking off earlier that day.
While he slept I pulled out my phone. Google was full of ideas on how to make this work. I made what must have been the most blatant “how to prepare your ass for fucking” purchase Amazon must have ever seen.
Two day shipping and my brain went into full on anal mode. He was away at work on the first day of waiting and I spent what felt like the whole day rubbing myself thinking about him entering my ass. I couldn’t wait for the package to arrive. On the following day the box came. I put on my sexiest lingerie and laid out the contents of the box on our bed with him looking on. He poured the lube all over my ass. Stroking his cock to the simple idea of the process. I told him to try putting his finger in slowly. Up to a point it was fine and then… nope, more pain. Our last ditch effort, we damn near emptied the bottle of lube on my ass. He took it so slow. I was aching for something to be put inside me. The buttplug was modest, certainly a beginners model but.. No. Nothing worked.
We had some very run of the mill sex that night. We were both frustrated. Me at my body and him at his still lingering desire to have anal sex.
The next day I had a lunch date with my girlfriend. She is the best, and I always feel like i can talk to her. But this was so embarrassing. How do you even talk to a friend about this over lunch? “Gee this soup is great… hey did i tell you that i can’t take my boyfriends cock up my ass?” I trusted my friend, but that is a bit extreme.
She had been down in the dumps for weeks. It had been 3 months since she caught her fiance cheating on her. She wanted to reenter the dating pool but she had lost her mojo. We talked about it a lot. Sex was a common topic of conversation between us. Her fiance and her were not quite as adventurous as me and my boyfriend and so she would always pry into what crazy shit we had been doing. A few weeks ago I was regalling her about the time he tied me up and did some forced orgasm play, I caught just the hint of her hand under the table slipping under her dress. I pretended not to notice as I played up some of the more explicit details and saw her face go flush and her breathing get heavy. I won’t lie. I went home after that lunch and thought of her as I ravaged my boyfriend.
Today’s lunch was different. This time it was her who was in a better mood and me with a gloomy cloud over my head. She could clearly tell i was distracted. She spent the entire lunch trying to suss out what was wrong. I kept deflecting and changing the subject to the mundane. By the end of lunch I could tell i was bringing her down. We were walking back to our cars when i blurted it out.
“Hey.. have you ever had anal sex?”
An elderly woman nearby cocked her head before heading into the restaurant.
“What?” my friend exclaimed.
I pulled her in close
“Anal sex, have you ever taken it up the ass?” I whispered.
“What brought that on?” she asked. “I mean, is this why you have been moping around all lunch?”
“So is that a no?” I proceeded.
“Well, yes and no.” she replied.
“What the hell does that mean?” I said incredulously.
“I have never had a cock in my ass, if thats what you mean. But.. I have.. Some sizable dildos at home with quite a long story to tell” she said with a wink.
“Wait, really?!”
“Yeah, what’s the big deal? It feels fucking fantastic.. Stick a big shaft up your ass and you have all sorts of interesting new surfaces to explore in and around your pussy, and that sensation of fullness.. Nngh… “ she smiled with a pseudo orgasm sound.
Listening to her describe it brought back all those hot thoughts right back to the surface and my panties were wettening again. I needed to get out of here.
“Nevermind… its.. Nothing” I deflected again.
She exhaled deeply.
“Well if you want to talk about it.. Or anything else. Just let me know”
I went to my car. I sat there in the driver’s seat thinking about my friend cramming a dildo up her ass while jilling herself off. I never really fancied myself a lesbian or even bisexual. But there is some something to the idea of caring about someone so much that you end up inadvertently sexualizing them. My friend was gorgeous. A thin frame like myself but muscular with small but perky tits. We had changed together a few times and she is really just the total package. Also, its hard to ignore how much interest she has in my sex life. I have caught her checking out my boyfriend a few times and even locking in a few long gazes at some inappropriate parts of my body. The thought of her ravishing herself with all those toys was more appealing than I could handle and I found myself slipping my hand into my panties there in my car. I had just closed my eyes when a soft tap on my window shocked me. It was her. She gestured for me to roll down the window. I did.
“Oh hey I wanted to remind you that I have no plans for OUR birthday next week.. If you want to throw me a surprise party” she stressed the word “OUR” because she shared her birthday with my boyfriend.
“Oh yeah.. Hey come on over and we will surprise you.. With balloon animals and everything” I jokingly replied.
“Cool… see you then” she replied seemingly oblivious to the fact that i still had my hand in my panties the whole time.
Oh.. I would make this a birthday to end all birthdays. She would get a surprise in the end for sure.
I was rejuvenated. The machinations in my head were running a mile a minute. I had less than a week to plan. First my boyfriend he was going to have a VERY good birthday but i wanted to make sure he was up for it.
I came bounding home from the restaurant. I gave him a long lusty kiss.
“Hey honey… remember when we tried some chastity play last year?” I said WAY too perkily.
“Ugh I do. It was tough but the things you did at the end to relieve my built up stress. Made it completely worth it.” he said cautiously.
“Good… I want to do it again.” still with way too much excitement in my voice. I tossed my hair like a cheerleader.
“Er… ok. What are the rules?” he said even more hesitantly.
“No cumming for a week. Its as simple as that” I giggled.
“So.. until my birthday… what are you planning?” suspicion dripping from his voice.
“Mmmmm youll see” I spun around popped my ass out towards him and bounded away.
Another amazon order… this time with the gift wrapping option. This order made the first one look like rosary shipments for a nunnery. I laughed at the idea of the poor sod who had to box up and gift wrap this order.
I could have made it easy but what would be the fun in that? He was so very obedient and I knew he would follow through on our agreement. As the week progressed the skirts i was wearing around the house got shorter and shorter and my shirts got tighter and tighter. At night I would lay sexily on the bed with my hand always resting but not moving on his perennially hard cock.
As for my friend. We had one lunch date before the birthday party but that wouldn’t do. Every other day I made up an excuse to call her. I’d push through the mundane discussion and immediately twist the conversation to my sexual exploits with my boy. It being over the phone who knows what she was doing while I softly told her about the time we fucked in the airplane bathroom or about the time I leathered up and tied him to the bed with some sturdy spanks? I don’t know what she was doing. But I had my fingers buried deep inside me replicating all the motions of my memories as I recounted them to her. I stifled my moans and sighs.. But only enough to pass off as a bad connection on the phone. For her part she stayed very quiet while i told my stories but sounded quite breathless when my stories were over. I had her baited on the hook. One last push over the edge should do the trick.
Our lunch date was the day before their birthday. I picked a niche restaurant. They were known for their raw oysters. It being the last day before the party my outfit was borderline vulgar for its purposes of teasing my boy. I had gone almost full schoolgirl. Tall boots, criminally short plaid skirt, tight white blouse, and to complete the ensemble plain white panties. I ALMOST wore my hair in pigtails but i thought that might be too on the nose. Her eyes near fell out of her head when she saw me.
“Well that’s quite the ensemble!” she tried to pass it off.
She was wearing a far more modest business dress as she had just come from work before taking the next few days off for her birthday.
“Good “ I thought “She is going to need those days off for how sore she is going to be”.
“Well I like to look nice for you” I said coyly.
I ordered a fair number of their finest oysters. When they arrived I downed a few and dispensed with the chit chat.
“So i was thinking about what you said last week. You are more adventurous than you give yourself credit for.”
“What do you mean?” she asked
“Well fucking yourself in the ass with a dildo isn’t exactly vanilla play” I said bluntly. “What else have you done”
“Nothing much I suppose… as you know my ex was pretty bland.” she said
“What about before your ex. What about in college? I’ll bet you got around to the fraternity boys.?” I said putting my tongue out suggestively before sucking down another oyster “Or did you make some time experimenting with the sorority girls”
She flushed at this and demurred slightly.
“Heh.. well.. I know my way around a vagina if that is what you are asking”. Shy shyly shuffled the oyster shells around her plate. “I mean… if that is what you are asking!”
I fixed my gaze on her. Fuck it I had her in the palm of my hand. I kicked off my shoe and lifted my foot to her leg. “That is precisely what I am asking”
She gasped but made no attempt to pull away.
“I never did when i was in college. Made my way around the boys and got more or less an education on how to take care of a man. But a woman..” My foot traveled higher I could feel her opening her legs underneath the tablecloth welcoming me in. “now thats a different matter entirely” I cooed.
I placed my foot on the front of her chair between here legs and kept it there.
“I’m not sure I’d have the faintest hint on how to please a woman.” she was writhing finally realizing i wasn’t going to move any further. Her hips shifted forward on the chair. My foot first glanced on wet cloth.
She was breathless “Oh I think you have SOME idea” she shifted forward more and suddenly my toes were pressed up against the wet soft cloth of her mound.
“Well maybe you can give me some lessons tomorrow.” I said sill staring at her.
“…lessons?” she was in a trance as she was clearly focusing her energy rubbing herself on my foot “… tomorrow..” she said slightly dejectedly realizing she would have to wait for her satisfaction.
“That’s right… lessons.. You are going to teach me two lessons you are going to teach me how to please a woman” I shifted my foot forward and moved my toes against her sopping wet panties. “And you are going to teach me how to take a cock up my ass” In one motion, I pulled my foot away, downed the last oyster, slapped the money for dinner on the table, and crossed to her chair. I pulled her head back and kissed her with a deep probing with my tongue. She tasted amazing and I left her breathless. She sat there panting.
“Lessons start tomorrow night”. I walked away with a bounce in my step.
I was so fucking horny. My teasing was going to pay off but i needed one more night of it. When I got home my boy was trying to focus on Tv to keep himself distracted. I could see his bulge just sitting there sustained while he watched some baseball. That won’t do. I stepped in front of the TV.
“One more day honey…” I said happily turning off the TV to his groans. I started undoing my blouse. “One more day and you can have these” I opened my bra to reveal my tight tits. “You can’t have this” I bent over in my white panties. “Yet… but no matter what.. You are going to get this.” I plopped myself in the soft chair opposite him. Pulling my panties down I gestured for him to go to the floor. I spread my legs with him kneeling in front of me.
“No touching… just watching” I spread my pussy lips open right in his face. Slowly driving my fingers inside me. With the days events I was already on the edge so his torture was brief. I climaxed and collapsed on the chair. He whimpered and I could see him fairly nursing his blue balls.
I woke up early the next day to make him a massive breakfast. He seemed in great spirits which is how I want my man on his birthday. During breakfast between bites he asked
“What time is your friend coming over”
Clearly he was calculating how much time he would have to suffer before she left and he could fuck me. Little did he know.
“Oh 6 o’clockish… I suspect she will be right on time”
We had a fun day. I made no attempt to tease him further as I wanted him in good spirits for tonight. I suggested that he should take it easy during the day as we had some tiring work ahead of us. He opted to limit his drinking for the same reason. Around 5 he and I shared a nice romantic but not overly touchy shower. We enjoyed looking at each other and it was truly romantic. Little did he know the depravity I had planned for the evening.
The box from amazon was massive and beautifully wrapped in paper with balloon animals on it (I did promise balloon animals) it was addressed to both him and her. I put it out on the living room table. The cake was in the fridge but.. Given how the evening was likely to progress I think we might just have it for breakfast. The large clock in the living room struck 6 at the exact same time as the doorbell rang. I had put on a nice black evening dress with red silk bra and panties. He was wearing a suit. When I went to the door my jaw virtually hit the floor. I both gasped and laughed at the same time.
In the doorway was my friend.in a white blouse with its top 3 buttons undone and a lacey blue bra underneath, a long pencil skirt, horn rimmed glasses, and her hair tied up with a somewhat frayed bun on the top of her hair and a pencil sticking out of it.
This kind of sense of humor.. To dress up as a school marm for what was obviously going to be a night of depraved fucking and sucking. Is exactly why she is my best friend. She even had a ruler which she proceeded to pull out and whack me on the ass as I led her to the living room. He was very confused. Which was just where i wanted him.
“So… its your birthdays… you can have cake” I made a frowny face “or you can have your presents” I gesture with a wide smile to the box on the table.
My friend spoke first “umm yeah.. I guess the presents…” she was hesitant. “Ok you both sit on the couch and open the box together. I want to see your reaction. “ I position myself on the soft chair opposite the couch (the one i had tortured my boy in the night before). I was electric with excitement. They both looked at each other. Him clearly starting to notice her cleavage. They quickly tore the paper away. Then the box. They looked inside and in one motion raised their heads to stare at my beaming face. His face was a combination of confusion and slow realization about how the night would progress. Her face could only be described as sheer.. hunger. Inside the box was a variety of about 10 different size and shaped butt plugs, three of which had our names engraved on them, 4 dildos of varying size and girths (ending with a massive black mamba), and a two gallon container of lube.
“Happy Birthday!” I shouted…then growling “Now take off your fucking clothes before I rip them off you.”
All three of us had been dealing with some degree of pent up hornyness. In some ways I was probably the least pent up. I got off yesterday and yet I was not kidding. I needed to be licked, fucked, and filled.. and soon. He wasted little time removing his coat and shirt. She literally ripped open her shirt and exhaled sharply. I lifted my dress over my head and before I could reach for my underwear I was basically body tackled back into the chair. MY friend was on me in a way that was almost feral. She kissed me deeply and pulled away her skirt and stepped out of her panties. She then made short work of my bra and panties before dropping to her hands and knees. She looked up at me… naked but still with those sexy silly glasses and hair in a bun.
“Lesson one in pleasing a woman” she said as she pulled my legs over her shoulders and buried her face in my wet pussy. I moaned hard as I put my hands on her hair. Her tongue was flicking over my clit before it entered me and somehow engorged wide. She made this motion three times and I could already barely breath. I panted as I looked across the room. My boy had emptied the contents of the box. She heard the sound
“You… bring that gallon jug over here… pour it on my ass and pick a nice big plug”
He did exactly what he was told. He carried the heavy container of lube… and Poured it over her petite frame. Her body immediately glistened from the slickness as she continued her campaign between my legs. He handed her one of the larger butt plugs. It had a nice red fake gem on the end. Without missing a beat with her tongue she reached behind herself and rubbed the lube in and around her pussy and fingered her asshole. After probing for a second she groaned as she plunged her finger knuckle deep right into her asshole. The sound of her groan echoing through my whole body. She grabbed the buttplug and plunged it in with another grunt and groan.
“Now our lessons are blending together… I grew to be able to take a buttplug like this. You will too. Hell we do our job right you might be able to take that black mamba over there… but at least you will be able to take this.” She reached over to gesture at my man’s rock hard member. She had stopped licking my pussy to talk and I was aching for more.
“May I?” she inquired politely. I nodded. She grabbed his ass as she spit sloppily on his cock. She was still on the floor and I flipped her over hungrily staring myself at her gaping and welcoming pussy. She was upside down licking the underside of his shaft and balls as I took my lessons to heart and tried to mimic what she had done to my pussy. First licking her clit and then plunging my tongue inside her and widening my tongue.
“Good student” she purred. Her cunt was drenched in lube and juices and the red gem of the butt plug was pulsating. I could feel it with my tongue as I entered her. The plug created a surface my tongue could play on in her pussy. This is what she meant. He clearly wasn’t going to last long and I felt bad for teasing him all week. It was time for his birthday present.
“Lets take this upstairs to the bedroom.. Grab the box. Its time for his present. “
We collected the toys and lube and headed upstairs. Once there I pushed him onto the bed. She bent down in front of him.
I put my finger on the red gem.
“This is your present. You get this ass to fuck.” I gently pulled out the butt plug.
She smartly propped her feet on his knees. His cock seemed to swell to the size of the black mamba dildo before plunging into her gaping asshole. AS one we all groaned, gasped, sighed, and moaned. Her being filled by his massive member, him finally getting the asshole he had wanted and me… well just looking at the scene had brought me to climax. He wasted no time pounding into her. I almost worried that he would hurt her before seeing her face. She was enraptured. Her eyes rolled to the back of her head.
“Better than the toys at home eh” I teased.
“Yeunghhhh” was all she could reply.
.
Source: reddit.com/r/sexystories/comments/8xp91o/mff_my_anal_friend_anal_oral