It all started when I began trying to convince my wife that she should try anal sex. I had always been fascinated with the idea. The various porn movies I had seen made it all look very simple and easy. Those gals seemed to like it, right?
So I did all the typical things guys do to try and work up to it. I talked her into watching a few porn movies. I tried bribing her with chocolate and flowers.
Occasionally, she would let me stick a finger in her ass. But even with that she would protest and complain that it did not feel good at all. I was using all the techniques I had read about but alas there was nothing that seemed to work.
My wife has a cute little butt which just makes the whole situation even more frustrating. She is a petite little brunette about 5'1" and 102 pounds. She has nice breasts, a slender waist, and one of those cute apple bottoms.
In fact, it was that heart shaped butt that first attracted me to her. It looks good no matter what she is wearing. And when she is in her bra and panties that is when I almost can't stand it. Sometimes I just want to feel my dick in her ass so bad I would do anything.
Well, one night we were having the anal sex discussion for about the one millionth time. I told her it was starting to effect our relationship, and that we should never let anything interfere with our love for each other. That we had to find a solution.
She agreed. Which kind of blew me away because I had not expected that kind of response. She explained that it just hurt too much. I accused her of not giving it an honest try, that it might take some practice to get everything to work right.
She said that my penis was just too big to fit in such a tiny little hole. That nothing quite so large had ever been in her ass before. She was afraid that it might damage her anus, or cause other problems.
I explained that her anus was a muscle like any other. And that she needed to let me work on it little by little... just like when she was a ballet dancer, and she had to condition and stretch her muscles to be able to dance that way.
She started to come around to the idea, and understood the logic, but she said she was still too scared to use that part of her body that way without knowing what would happen.
What she suggested next freaked me right out. What she said pinned me into a corner I had never ever anticipated. My wife is no dummy, another reason I fell in love with her.
She said that maybe if she saw me take something in my ass that would be about the same relative size as my penis would be to her, then that would give her some encouragement that my penis would actually fit inside of her ass. She wanted to use me as a guinea pig to see if all that stretching and conditioning of an anus I was telling her about would really actually work.
I was speechless. What in the world was I supposed to do now? I didn't want anything in my ass! I wanted MY penis in her ass! But as usual her logic was impeccable. I had to think quickly. I had to respond with something clever. My mind was scrambling to come up with a reasonable answer.
The shoe was on the other foot now. There was nothing I could say, that if I said, would not then strengthen her argument against trying anal sex. I was "screwed" so to speak. These are tough moments in a mans' life. When a woman has us boxed in a corner with logic that can not be undone.
"What, are you chicken?" she chided. "All this time you have been trying to get me to look past the obvious pain of trying anal, and you wont subject yourself to what you had in mind for me?" she questioned.
"But uh...." That was all that came out of my mouth. That was the best I could do. That was all my mind could muster up.
"What, don't you trust me?" She said in that sly voice she uses when she knows I'm cornered. And of course that was exactly what I would always say to her when she declined my advances to try anal sex. "Don't you trust me." Now it was the other way around. How ironic.
She came over and put her arms around my neck. "I would never do anything to hurt you," she said coyly. "Besides, it might be fun to see you squirm just a tiny bit" she whispered running her finger down my neck over my Adam's apple.
She walked over to the cabinet and pulled out a cloth tape measure she used for sewing. "Let's see just how big of an object we will need," she said as she unzipped my pants and fished my penis out. She began to stroke and lick my penis making it hard.
I was frightened and curious at the same time. I was not really sure where she was going with the tape measure, but the licking and sucking felt pretty good. I was definitely getting a raging hard on.
"Come on lets see just what we are dealing with here mister," she held my cock out and laid the tape over the length of my penis. The tip reached the Â¼ inch mark just past the eight inch mark. "Looks like eight and a quarter inches, wow that is allot of penis for a little gal like me to take up my ass," she gasped.
"Now lets do some math. I'm 5'1" or 61 inches tall and you are 6"2" or 74 inches tall so you are approximately 20% taller than me. So an object for your ass would need to be approximately 10 inches long for you to experience what your 8 Â¼ inch long penis would be like in my ass."
It was becoming clear to me what she had in her devilish little mind. She intended to shove something ten inches long up my ass to show me what it would feel like for her to have me shove my penis up her ass. Like I said, she is no dummy.
Then she took the cloth tape measure and wrapped it around the girth of my penis at the thickest part. "Six and five eighths, wow that is pretty thick for a little gal like me," she said coyly. Then she put my penis back into my trousers and buttoned them. Which was totally unfair. Leaving your man with a boner like that is just not right.
She grabbed a scrap of paper and started writing "So lets do some more math... hmmmmm. Six and five eighths plus 20 percent equals about eight inches. And an eight inch circumference divided by PI comes to roughly two and a half inches in diameter" She held up her hand and made a "C" shape with her thumb and fingers. "Probably about like this," she said confidently winking with a half smile.
I looked at the size of the "C" shape she was making with her dainty little hand and realized this was going to be a fairly uncomfortable situation for me. I'm pretty sure nothing of that size had ever come out of my ass much less go in.
I don't think my brain could comprehend the situation really. Like I said she is no dummy. And heck if I could do any of the math she was rattling off. Although I'm sure she was probably right, she always is. The "C" her tiny hand was making looked enormous.
"Ok dear, what we are looking for is an object at least eight inches around and at least ten inches long. Or at least ten inches of it needs to go inside your ass. Maybe we need it to be about fourteen inches long so I have something to hold onto and pull it back out again. Sound about right?" she said in a purely scientific voice as if she had just split the atom.
"I know the perfect thing to use for a job like this. Let's go to the supermarket and we can find a cucumber that is just the right size," she said in an exited yet determined voice.
She picked up the car keys and grabbed me by the hand. I was feeling butterflies in my tummy now. How in the world was I going to get through this ordeal? My virgin ass was going to get skewered with 10 inches of cucumber that was 2 Â½ inches in diameter, and all this was supposed to be fair? Holy Crap!!
My knees were weak and wobbly as we walked into the grocery store. My brain was still spinning around trying to make some type of logic that would stop this humiliating process. About the only thing that came to my mind was the Gay card. You know, what if it turns out that I like it? I mean that had to be a logical reason why she should not do this, right?
But then I could just imagine her answer. It would be something like, "well you don't seem to have any problem sticking your penis in someone else's ass, what about that?" So I gave up on that line of logic.
She pushed the cart up and down the aisles looking for something. We were over in the pharmacy section. She could not find what she was looking for so she went up to the pharmacy counter. She leaned over and asked, "excuse me I'm looking for personal lubricant and latex gloves?" I just about passed out. I looked the other way and pretended not to know who she was.
The pharmacist came out to the counter and began to explain to her all the different types of personal lubricant. "Well there are some that are a gel, and some that are a liquid, and we have some that provide a warming sensation, " he said in that clinical tone as if he had no earthly idea what people use the stuff for.
I went over to the magazine rack and started looking at the motorcycle magazines. About five minutes later, My wife came over. She had three or four bottles and tubes of different lubricants, and a huge box of latex gloves in the cart. "Ok let's go take a look at the produce section, " she said in that sly voice.
My knees were weak and there were butterflies in my tummy. "Hey, how about if I just read these magazines while you go find the... the... er... uh... thing... you are shopping for," I responded.
She grabbed my hand and pulled me along. "Don't be such a baby, besides this is the fun part, you will want to help me pick just the right one."
The store seemed to be spinning and I felt like I was going to pass out. I could not help but notice people staring at the contents of our shopping cart. Then she pulled out the cloth tape measure. This was beyond humiliating.
She reached out, picked up a cucumber and ran the cloth tape measure down the length, it was huge. "Let's see... hmmmmm... too short, " she placed it back down.
Too short!! What the heck... that cucumber was huge! She moved all the cucumbers around and out of the way. She picked up what seemed to be the biggest one in the bunch and ran the tape down the length. "Thirteen inches, well I think we can make that work", she said in an excited voice.
She wrapped the cloth tape around the fattest part of the cucumber. "Nine inches, hmmm well that will have to do. This is the only one long enough. You can handle a tiny bit more than the eight inches we were looking for", She said as she reached down and patted my ass.
"Now we need to find a few smaller ones to open you up with, you know to work up to the full sized one. How about this one? It seems to have a little personality", she held up a long slender cucumber that had a large bulb shape on one end.
I looked at that gleam in her eye and stood silent not really knowing quite what to say really. She picked up about three more cucumbers and placed them into the cart.
As we checked out at the register, I felt waves of panic creep into me. Everyone seemed to be staring at what my wife was placing on the conveyor belt. I'm quite sure the checkout gal had some inkling what all this stuff was for.
We got home and I flipped on the TV pretending none of that stuff was sitting on the kitchen counter. I figured maybe she would get distracted or something. She went into the bedroom and came back out with two pillows and a bath towel.
"Ok sweetie, climb out of those pants and lay down on these pillows.", she said as she stacked the pillows one on top of the other and draped the towel over them.
I did not know what to do, I just sat there motionless. She came over and stood me up and began to undo my pants. She fished out my penis and began to work on it sucking it into her mouth. "Come on sweetie, just relax, I wont hurt you, just lay down and I will give you a nice massage."
I stepped out of my pants and she placed me over the pillows with my legs spread wide apart. She sat between my legs and coddled my scrotum, running her fingers up and down the insides of my thighs. "Just relax sweetie, this feels good right?" she continued the massage.
Then I heard her reach into the grocery sack. I heard her open the box of gloves and put them on her hands. She slapped my ass with both gloved hands at the same time. "Are you ready to get fucked in the ass, dear?" she asked a she squirted lube out of a tube onto my tight puckered hole.
Before I could say a word she shoved her middle finger up into my ass as far as it would go. My ass cheeks clinched together and I buried my face in the carpet. "Come on, relax that cute little butt for me sweetie, just relax" ,she cooed as she patted my ass with her gloved hand and wiggled her finger from her other hand all around. I actually felt a boner starting and had to adjust my penis so it was pointing upwards.
Of course she saw this and reached down between my legs and grabbed hold of my now hard penis. "Mmmmm so this is feeling good then, you like this anal stuff don't you?" , she chided. "Take some more my cute little butt slave, mmmmm feel that?" She jammed a second finger alongside the first. I jerked forward a bit trying to get away from the fingers twisting and shoving in my ass.
"Come back here silly, come on, don't try to squirm away, we are just getting started. Just relax, lets try the first cucumber. Here, get up on your hands and knees and stick your ass up in the air for me. I want to make sure I can see what is going on." She slipped her fingers all the way out and patted my ass. "Come on sweetie, get up on your knees" , she taunted.
I begrudgingly got up on my knees. She scooted up so that her face was inches from my ass. I felt more lube being applied to my ass. She pressed the cool tube right to my ass and squeezed some lube right up inside me. She shoved a finger in and twisted it around. My ass started to feel hot. "How does that feel sweetie? The pharmacist said this warming lubricant would help add more sensation".
Her finger pulled out and I felt a cold blunt object press against my anus. "Ok, here is the first cucumber, it is not very big try to relax." I tried to relax but it just did not feel right. She kept pressing but all it did was move me forward. "Wow this is harder than I thought. Don't move, I'll be right back." She said. I heard her fumbling around in the kitchen.
She came back and sat down again. "Ok, I have a carrot that is a bit smaller than the cucumbers, let's give it a try." She said as she squirted lube out and rubbed it onto the carrot.
I felt the cold carrot slip slowly up into my ass. It wormed it's way deep, much deeper than her fingers had gone. "That's good, I'll just let it sit there for a minute so you can get used to it." She said as she cupped my scrotum with her other hand. About a minute went by and slowly she began to withdraw the cool carrot until just the tip remained, then she pushed it back in even deeper.
It was a strange sensation to feel something slip way up inside me like that. It didn't even matter if I tried to clinch my anus closed, it still slipped right in with all the lubricant and the slim tapered shape.
What felt really strange is when she withdrew it. It felt warm and left my ass feeling very empty. Almost like I wanted it to go back in. I found myself relaxing my anus and tilting my ass upwards as if to anticipate the slippery smooth carrot.
"Ok, lets see if the little cucumber can fit now," she said as she slipped the carrot all the way out. It felt weird to just be up on all fours waiting for the next thing to be shoved into my ass. I could hear her slathering lube all over the cucumber.
"Just try to relax now. This is just a tiny little cucumber. It's not much bigger than the carrot really. Come on you can handle it. Open up for me sweetie," she said as she pressed the cool cucumber against my anus.
She began to push a little harder and twist the cucumber around a little bit. "Come on baby, take it up your butt, open up for mommy." (ok that mommy thing was just a little weird to hear her say, but honestly it kind of turned me on a bit)
The cucumber suddenly sank into my ass and went real deep all at once. My whole body tensed up a little. "Good boy, that's it, relax your ass for mommy." (ok, there's that mommy thing again. I didn't know what to say so I just kind of went with it.) "I'll just let it sit in there for a minute so you can get used to it, baby." She held the cucumber firmly embedded deep into my ass, and patted my ass cheeks with her free hand.
She began to move the cucumber up and down and side to side kind of like stirring a spoon in a pot. "Good, that's it, just relax." Then without warning she pulled the cucumber out fast and jammed what felt like two fingers up my ass twisting and turning them driving them deep. I lurched forward, mostly out of surprise, but also because she was shoving so hard. "Oh yeah, that is much looser, let's fuck you a little and see how you do with it."
She pulled her fingers out and shoved the small cucumber back in slowly twisting it back and forth. She got up on her knees and held the cucumber with both hands and twisted it all around. Without warning she jerked it all the way out, then pushed it back in real slowly. "Oh that's a good baby, take that cucumber up your ass for mommy."
She continued to impale me slowly, twist around for a minute, and jerk it out quickly. My ass was starting to really relax now. When she would jerk it out, it came out with almost no resistance at all. It felt kind of weird, kind of sloppy. She shoved it in slowly and more deeply than before and just left it there. I heard her squirting out some more lube.
She pulled the cucumber free and shoved what felt like three or four fingers up my ass twisting them all around. "Wow, I think you might be ready for the big one. Here lay your head down on the pillow and keep your ass up like that." My brain was spinning now. I did as she instructed. I could feel her fingers twist around feeling all around inside my ass.
She shuffled around and I felt her fingers withdraw and a new colder cucumber wedge at the entrance of my ass. It felt like it might as well be a bowling ball. When she would push on it nothing would happen except that my ass would move forward. "Hmmm, maybe you need something bigger but not quite this big yet." She removed the cucumber from the entrance to my ass.
She placed a different cucumber to my ass and began to push. "This is the one with a nice fat bulge in it, you might like this one allot. It has some bumps on it too. Come on open your ass for mommy." She shoved hard and it sank in about two inches. My ass seared with pain and I lurched forward trying to get away from the invader. I ended up laying over the pillows again clinching my ass cheeks tightly.
"Oh I'm sorry sweetie. Is that too big?" She said as she held it firmly to keep it from dislodging. "Just relax, it will fit, just lay there for a minute, I promise not to push it any further until you are ready." She held the cucumber in place and stroked my tightly clenched ass cheeks with her free hand. After a minute my ass cheeks began to unclench.
"Come on baby, just relax your ass for mommy. Here I'm going to push just a tiny bit now." She began pushing and it slowly sank past the thick part and then slid all the way inside quickly up to the hilt. It felt much different than the last one. It went much deeper and it felt wedged firmly in my ass, like it was splitting my insides apart.
"Ohhhhhh yeah, see that goes in nice and smooth baby. Mmmmmmm look at how big your ass is stretched open, wow that is allot of cucumber for mommy's little baby." She said. I could feel her running her finger around the base of the cucumber wiping more lube onto my stretched anus splayed widely around the girth of the cucumber.
Before I could even get acclimated to this new larger object, she began to move it around. She tried to twist it but it would not budge. My ass was gripping the large cucumber tightly. "Wow, that cucumber is stuck. We need to pull it back out and get some more lube inside your quivering little ass baby. Just relax while I pull it out. I promise to go slow, just relax."