My wife’s older sister was a nurse and replied in a very calm “I’ve seen it all” voice - “Lori. You must understand that anal sex is no big deal if it is done carefully and with the right preparation. I make Tony do it when he forgets his condoms because I don’t want to get pregnant. I prefer vaginal sex, but I can tell you honestly that I really don’t mind anal intercourse now that I’m used to it. I sometimes think Tony forgets his condoms just so he can do me there.”
Everyone laughed but me. I’m a shy kid from a Catholic family and in all my life I had never heard of a woman having anal sex before, much less wanting it. I must be incredibly naïve because I didn’t know it was even possible. Just the thought of anal sex blew my mind. My relationship with Sue was strictly make out sessions followed by an occasional blow job or on rare occasions, vaginal sex, and this didn’t start until after I promised to marry her. I got very nervous when the friend said “How about you, Sue? Do you let Mark fuck you up the butt?”
Before she could answer, the older sister quickly sniped in with “Sue would never let him do that. She’s too much of a chicken.” Then in a really mean tone she added “Besides, she’s such a little prude - I’ll bet she’s never even swallowed before.”
Unfortunately, the sister was right. Sue was not only a prude but a little weird. She’d make out passionately until our lips bled, and she’d stuff my hands under her top and tell me to grope her tits, but she tried to avoid real sex because she said it was “yucky”. Her blow jobs were always neat and tidy, done with a clean soft towel under my butt to catch her drool and another one waiting nearby to collect my fluids when I came. If we fucked, she was just as bad. Sue was on the pill because she claimed to be allergic to condoms (said she found out while having sex with another boyfriend), but she didn’t like the mess that sex left in there. When we finished, she’d run to the bathroom and sit on the toilet until all the semen drained out, and that’s how it always had been since our first time. You would never find any wet spots in our bed.
So I smiled nervously as we waited for Sue’s answer. Her face turned dark red and it looked like she was about to explode. Sue had a nasty temper and you could see fire in her eyes. Several times she started to say something but stopped in mid sentence. Finally she stood up, grabbed my hand and dragged me to her bedroom, slamming the door behind us as the other girls laughed and threw insults in our direction.
Sue stood for several minutes, crushing my hand with an intense grip. I could tell she was trying to figure out what to do next and that she was steaming mad. I told her we should leave and go to the mall or something, but then she started to undress slowly and very softly told me to strip. When we were naked she covered my erection with hand lotion like she always did when we were about to fuck and hopped up on the edge of the bed doggy style. That was her favorite position and I was happy she decided to play instead of fight with them. When she motioned for me to get in, I slid into her pussy and started fucking the way she liked it.
“No, you idiot” she hissed. “Weren’t you listening? You have to stick it in my ass this time!”
“Are you sure you want to do this?”
“Stick it in my ass now or get out and don’t ever come back!”
I figured either way I couldn’t lose, so I withdrew from her vagina, laid my tip against her asshole and started to push. She was extremely tight and it took an incredible amount of effort just to get my head inside the rim. As soon as my head was inside her ass, I came instantly which helped because cum was a much better lubricant than the cream she used. Following her direction, I continued to wiggle and push until I was all the way in. Once deep inside her, she told me to stop and just hold myself there until she figured out what she wanted to do next. I waited for her instructions as she whimpered in pain.
“Holy shit this hurts. Why do people do it?” she cried as I waited.
“OK. Try fucking me slowly.”
I began to slide my erection in and out, but it was a constant fight because her muscles were always trying to eject me. Several times her rectum pushed me out completely and I had to fight hard to get back in. I could tell that Sue was really in pain. I fucked her slowly until her ass pushed me out again so I stopped.
“I can’t believe people do this because it really fucking hurts.”
“So, what do you want me to do now?”
“Get back in my ass. I’m not going to let my sister make a fool of me.”
I pushed back in and started fucking her slowly.
“Try going faster.”
I picked up the pace a little.
I came again and the lubrication allowed me to go faster still. Sue seemed to like that.
“Now that’s better………oh my…...…. this is nice.”
At the time, my wife had ample soft hips which I adored. I grabbed two fistfuls of flesh and started humping her ass hard. Her tanned skin turned purple where my fingers dug deep into her flesh.
“Mmmmmm…… OK. That’s better. Can you go a little faster?”
After I picked up the pace a little she said “Harder. As hard as you can do it.”
I did what she asked and she really seemed to enjoy it as our bodies were slapping together loudly. Suddenly Sue started screaming out phrases like:
“Yeah baby! ...... Fuck my ass!!........ Fuck it baby! …… Oooh yeah baby this feels good! …… C’mon baby! …… FUCK HARDER! ………….. Give it to me baby! ……Yeah baby! ……. Fuck my ass!!..... Oh fuck yeah! ..... Hell yeah! ...... C’mon mister! Fuck me harder!”
It was all an act and Sue kept up the running commentary like the announcer calling a horse race. Thankfully, I kept coming because the friction and heat in her ass was burning my penis. Each ejaculation lubricated her and cooled things down for a few seconds. Then I could fuck harder which made her scream louder. I loved being twenty because even though I came quickly, I could come often and as we learned from fucking her pussy, unless the lubrication wore out and the friction got too bad, my erection never gave up so I could go like this as long as she wanted me to without stopping.
It didn’t take much longer to realize my semen wasn’t enough for this hard pounding, so I pulled out. She started to yell at me to get back in but then saw me putting more cream on my penis. Just to make sure there would be enough, I inserted the bottle in her ass and squirted a bunch in there too. She got impatient and ordered me back in so I held my thumb against her asshole to keep the cream dammed up while I put the bottle away. Then I jumped back in and resumed pounding her.
It was a lot cooler now and I was able to maintain a steady hard pace. After five more minutes, her exaggerated dialog turned into strings of long moans that changed pitch with every thrust. I had never heard Sue ever make any noise during sex before, but now she was being very loud. I was fucking her ass as hard I could but trying even harder to keep from laughing at the sound of air being pumped into her rectum with every thrust. Ever since I put the cream in there the ass fuck sounded like an old pump with bad diaphragm, so I decided it was time to let some of the air out.
I let her ass push me out just far enough to where she let out a long stinky fart. When it finished, I quickly put just my head back in to keep from losing all the cream I had in there. This gave me an idea and I started to play with Sue by moving just the head of my penis in and out of her asshole while I rubbed more cream on my penis. This sensations made her scream for me to get back in. She cursed until I jammed myself in as deep as I could go and then I held myself there. I waited until her shrieks for me to start fucking became intense, then I’d go back to thrusting her. Remembering how fun this was, I repeated it any time her ass filled up with too much air.
As we kept going, her moans were getting really annoying and I was running out of new ways to play with her ass. I eventually got bored just thrusting her so I pushed her flat on the bed and lay on her butt trying to push my erection even further up her ass. She moaned for a little bit, but she must have been getting bored too because suddenly she kicked herself free and jumped up to go over by the door.
She turned to me and whispered “They’re there, listening to everything!”
A river of cum and cream flowed out her butt and hit the floor with a splat. She saw me pointing and gave me a dirty look and signaled for me not to laugh. Suddenly she let loose a loud fart that sprayed cum all over the door and I started to laugh hysterically. Grabbing one of her towels she wiped herself off and cleaned up the splatter on the door saying “Why is sex with you always so frigging messy? You’re going to have to help me clean all this up later.”
I sat up on the edge of the bed and pretended to gag at the smell of her fart, so she mashed her tits into my face and gave me a strong hug. She started being playful and I loved sucking on her nipples and that caused me to quickly grow another erection that rubbed her leg.
“You are such a horn dog,” she said loudly as she wiped me off, “I guess I’d better take care of you before you hurt somebody with that thing, so open your legs.” She finished her sentence by kneeling on the floor and licking my erection with lots of moaning and dirty talk. She kept shouting “You’d better come in my mouth!” which surprised me. Blow jobs with Sue were always very quiet and extremely boring, and she had never even attempted to swallow before. Instead, she always made me come into a towel. She had drilled into my brain that I had to follow the same routine every time so when I was ready to come, I tapped her on the head and whispered “OK sweetie, I’m ready.”
Instead of reaching for her towel, she grabbed hold of my balls and started sucking hard on my erection. Between her holding my balls and putting such a strong suction on my penis, I had the most intense orgasm I had ever experienced in my life. Her suction made my testicles feel like they were being vacuumed clean. I remember shouting “Keep sucking! Keep sucking!” until we heard a thump as someone bumped the door. Sue paused and I thought she was done, but then she sucked harder which was wild. When I couldn’t take the sucking any longer I grabbed the back of her head and started fucking her mouth hard until I came again and then let her up.
“That was the best blow job you’ve ever given me!”
She opened her mouth wide.
“I swallowed both times!” she shouted at the door “and I want more.” Sue made sure everyone could hear.
Her sister had a glass against the door again and we both had to cover our faces to keep from laughing at the noises they made trying to listen to us. I let out a giggle so Sue stuffed a nipple in my mouth and pushed me back on the bed as she whispered “shhhhh!” I wanted to suck on her tits but she wanted to keep showing off for her sister, so she bounced her tits on my face and pulled on my penis until I got another erection, and then climbed on top of me. I expected to feel the warm moisture of her pussy this time but she slowly pushed herself down until I was deep in her ass again.
Sitting up straight and grimacing in pain she managed to shout out “I love you back in my ass!” every few seconds. I motioned for her to get off since I could tell she was hurting but she wouldn’t budge. Her rectum was extremely tight and much hotter than her pussy had ever been. The rectum walls pulsated as her muscles instinctively tried to force me out of her bum but the weight of Sue’s 140lbs sitting on my penis overpowered anything her muscles could do to expel me and I remained deep inside her.
The pulsating caused me to come in rapid fire succession, but it was weird – not my typical ejaculations. I guess Sue liked it because she moaned with every spurt whispering “That feels really neat when you come like that!” Realizing the sister and friend were still at the door, she shouted “Why haven’t you fucked my ass before now? You need to do it more often. This is fun!” The rapid fire spurting caused my penis to go soft faster than normal and her ass forced me out. I pulled her down on top of me as cum drained down my balls while I cuddled her.
I wanted to rest but she was too excited. She kissed my face as she whispered “You don't know how much I really appreciate what you just did. You saved my life. I really mean it. I owe you forever! Thank you.” Her affection gave me another erection and she giggled when she felt it poke her. Then she laid her head on my chest and said “You just stay there and relax. You earned it.”
I quickly fell asleep and when I awoke, Sue was snuggled against me. It was nice and warm under her blankets and I felt really happy being there. Ever the neat freak, while I was asleep, she washed me off and cleaned herself up as well. When she noticed I was awake, she whispered “You can’t believe how much cum is still flowing out my ass. I have to keep stuffing paper towels in there to try and absorb it all.” Then to prove it, she threw back the covers and rolled over to show me a big wad of flower print kitchen Bounty jammed in her crack. It was the funniest sight I have ever seen.
I shivered and pulled the covers back over us. Then I went back to sucking on a nipple as she said “Donna and Lori asked me if you would fuck them too. You made them jealous because Tony only lasts a few seconds and Lori says Jim isn’t much better. You come quickly too, but I guess they don’t stay hard like you do.”
Neither of them was pretty. In fact the friend was downright ugly, but I always fantasized about the sister because she had massive tits that were easily 46EE if not bigger where Sue was a firm little 34B. My mind raced with thoughts of Donna’s giant tits smothering my face but before I could stop myself, I said “You know I can’t do anything like that. I am yours and yours alone.” Sue smiled and pulled my face back to her chest. “That’s why I love you.”
She noticed I had an erection again and said “OK you dog. One more time and then let’s all go out for subs.” As I lay on my back, she turned around under the covers and gave me a very passionate, slow blow job. These were rare but when she did them she called them LSDs for Long, Slow and Deep. Not wanting to get her clean sheets wet, when we finished, she swallowed every drop again. “I’ll have to try and remember that,” she muttered to herself as she told me to get up and get dressed.
I always hoped this experience would lead to a more adventurous sex life for us, but unfortunately, this day would never repeat itself. For years I promised Sue anything to get back in her ass or to have blow jobs like the ones she gave me but it would be a long, long time before we ever did anything like that again.
This story is part of a collection of stories my therapist is having me write to help me deal with my terminal illness. After reading the first set of stories, she told me that they’re “pretty darn good” and referred me to her lawyer to copyright them which I did. The rights now belong to my stepson, so please do not copy or distribute any part of this story without written permission. © 2010 by OldFriend2010@breakthru.com All Rights Reserved.