Letter to a Friend
Letter to a Friend
By: Sassy Sue

My Dearest Samantha:

I am so pleased that you wrote me about your contemplation of trying anal sex. We have shared view points on this subject, exchanged a ton of porn of women taking cocks up their ass. I can relate to the confusion of giving up your anal cherry. It is your last cherry to give up so I know it weighs heavy on your mind, so I will share with you my opinion.

With all this, chat about ass fucking, I guess I best give my two bits about a subject that is near and dear to me. For years, I was of the opinion that my ass was for sitting, slapping, fondling, and many other functions. But never and I mean NEVER did I think my asshole was to be fucked, to have a man shove his cock up into my Hershey Highway, not me girlie, no fucking way. That has been my untenable position for years. Many men (some women too) had tried to shove their cocks in my virgin ass but I refused all attempts to pluck my anal cherry.

It seemed the longer I held out, the more persistent lovers became. I let my lovers rub my anal ring; probe my tight little hole with the pads of their fingers, lick my brown eye with their rigid tongues. Yes, lovers of both genders were knocking on my backdoor trying to gain admission. I found this to be scintillating and intriguing and my interest peaked. I read everything I could find on anal sex, I watched porn videos and looked at porn pictures. Women of all shapes, sizes, and ethnicity were getting the asses drilled by men. I chatted with women on all sorts of web sites and talked to my girlfriends about anal sex.

I heard horror stories of how some women tried anal sex to please their lover and it was the worst thing they ever did sexually. Some women claimed it was painful, they would crying during their ass fucking because the pain was so intense and the felt their lover's cock was ripping their assholes open. These remarks did nothing to assuage my dreads of taking a cock in my backdoor.

Other women told me they could relate to the fear of anal sex but once they jumped the hurdle of their fear and took their first cock up their ass for the first time they could not wait for a second time. They just loved the feeling of a man's cock in their ass, filling them, enjoying the pulsations of a throbbing cock pumping hot come into their ass. That aura of tightness as their sphincter muscle is gripping the spear that is impaled in their ass and riding it to orgasm as their pussy comes. Many reinforced the fact that it had become a very important part of their sex life.

Surprisingly, a few women even said, they would rather have a cock filling their ass than their pussy. By now, I was really fucking conflicted and YET I had the insistent, nagging urge to try something, to take something and put it in my ass. I had to experience this for myself. Does this mean that I am destined to be an ass slut?

Like you, my fascination with anal sex was morphing from a causal interest into a fricking obsession at an alarming rate. I would masturbate and my finger would wander to my asshole, I would rub my juices on my asshole. The next time I would get bolder, braver and I would push my sphincter open with the tip of my finger feeling it gasping trying to close on my finger pad. I would never penetrate my virgin hole but I sure came close. Cucumbers, vibrators, my fingers all visited my backdoor and begged for admittance to my virginal craven, but I resisted the mounting temptation. I crave the feeling, I dream of a man with his thick cock fucking my ass, pumping his sperm into me and it was becoming addicting, I wanted to be one of those women with that had telltale gob of come leaking from her asshole after a deposit has been made. I would have sex and let the guy rub my virgin hole with the head of his prick, maybe come on my asshole or really step up and let him finger my hole without entering my ass. I was so fucking horny after this entire mess of pre-cursor ass fucking.

My second objection was the fact that a guy could shove his dick in my poop chute and when he pulled out, he would have my crap on his dick YEW, which is not the least bit appealing. My friend Jesse and I had many talks about anal sex and lots of wine. She was a strong advocate of backdoor sex. Her husband had been fucking her ass for years now and she said she really enjoyed taking his cock up her ass; in fact she had to have his cock in her ass on a regular basis. She taught me that a good cleansing (enema) would clean me out before taking it in my ass so there would be no poop on his stick. Many times, she played with my ass during our sex and each time it was so fucking hot and yes she would make me come.

Now I was twenty-three and decided that my goal for 2012 was to lose my anal cherry. Jess volunteered for the job. I was ready for her to go where no man had gone before. I spent the day preparing for her, a wax job, and an oil massage to insure my skin is soft and supple for her. A new pair of sheer panties and matching bra to tease her, anticipating she would not leave me wear them for long. The doorbell rang and we were off on our adventure of deflowering my asshole.

Several hours later, my pussy had experienced her tongue and a strappy. My cunt flushed with a fresh fucking, my tits had been pinched, bit and sucked. My asshole had been flushed clean and now Jess was fingering my backdoor slathering it with lube as my tight little ass stuck up in the air. Jesse kneels, my legs spread for her, and the head of her thick strap-on dildo poking my backdoor. Her strong hands had me wide open, my anal ring relaxing as her finger worked the opening, first one finger, then two fingers and finally three fingers twisting in my asshole. Pushing back on her fingers, moaning like a whore on payday, I could feel my asshole stretching. Then nothing, a vacancy, which moments before the void had been filled and I had pleasure.

The head of her dildo, pressing on my anal ring and blossoming like a flower the thick dildo pushed past the opening. I could feel my asshole stretching, the pain building from a dull ache into a searing flash as the cock entered my virgin hole. She pushed, I am shrieking and an electric jolt shoots up from my ass to my brain. Her hands on my hips Jesse begins to fuck my ass slowly, I am sweating profusely and my cunt tingling, on fire. Long, slow, deep penetrating strokes filling my ass and I throw my head back and push to take more of her dildo. Jesse changed her speed and fucked me until I literally collapsed and she eased the dildo from my puckering asshole.

With Jesse's support, her dildos, and a fat strap-on cock she plucked my anal cherry on that Saturday night. I had a very sensual experience, getting my ass fucked for the first time, but of course it was not the same as a man, but now the fear was banished.

A week or two later I was comfortable with anal sex but I still had a lingering question, "What did it feel like to have a man's cock in my ass and come in my ass?"
Valentine's Day 2012 was just around the corner, and I had a date with my Fuck Buddy Mark who I thought he would be the perfect man to be the first man to fuck my ass. He was always a considerate lover and would never hurt me so I went about my preparations for the night.

I wore a sexy black dress, a tiny black thong, and a wispy smoky bra. We went to a fine restaurant for dinner and a couple of drinks. A leisurely drive to his place and a little foreplay one in his home, it was not long before we were in bed fucking our brains out. Mark teased my asshole but never broke my anal ring. I was thirsty so I slipped from the bed, naked I walked to the kitchen and got something to drink. I stood at the counter, looking out the window at the city lights.
Then I felt Mark's strong hands on my shoulders, his warm breath on my neck as he whispered in my ear.

"So my kitty, I understand that you want to experience a cock in your ass and you think I should do the honor. I am flattered! However, do you really think you are ready to take me? Can you take the pain as I enter your most private orifice? Stretching your tight bud with my thick prick and ease it into you until your feel my balls spanking your pussy as I fuck your ass relentlessly until I fill you with my hot cream, will you take it?"
His hands cupping my breasts, I muttered "Yes."
Turning to return to the bedroom so I could surrender my ass to Mark I took a step when Mark stopped me. Spinning me around, facing the counter, Mark pressed me against the edge.
"Here, now, I will take your cherry ass my darling Sue."

Kissing my neck, Mark was asserting his body weight on me; I could feel his erection touching my ass. I leaned forward and my tits, my nipples were now touching the cold granite countertop. Mark pushed me lower until my tits squished flat on the cold granite countertop. Mark moved his hands down my leg and began to raise it level with the countertop and one level he eased my leg onto the countertop. My sex and asshole were completely exposed. My arms stretched out in front of me on the counter and I raised my head as Mark is dribbling a stream of lube down the crack of my ass. Trembling, my pussy wet from fucking now was oozing nectar. Marks hand cupping my swollen pussy lips, spreading the lube, melding with my nectar, and opening my tight sphincter. Mark, reaming my anal ring with his fuck finger and then he had his finger in my ass up to the third knuckle. Then a second and a third finger, my asshole relaxed. Then I felt nothing but a vacant feeling in my ass. Now Mark's cock was sliding up and down the crack of my ass. More lube, everything was slippery, I could feel lube and pussy juice easing down my thigh.

The head of his bulbous cock bearing down on my anal ring and my bud was opening. The head of his cock was in me, I moaned he pushed in deeper, slowly, my asshole gripping Mark's thick, hard shaft and the searing pain made me think my ass was being split in half. Then his balls were touching my pussy. OMG his cock is buried in my ass! He began to fuck me with long deep strokes, faster with each stroke and the initial pain once again subsided. I loved his cock in my ass. Now Mark is slamming into my ass, grunting, groaning, and his hands on my ass cheeks keeping the spread as we fuck. Mark slammed into me, shoving my hips against the edge of the counter and my asshole is being filled with his hot cream.

Mark came in my ass, his come seeping from me as he extracted his prick from my backdoor. I was now one of those women with the telltale trail of come leaking from my asshole; I was elated, felt so alive left with a desire to do this again. We headed to the shower where I kissed him and thanked him. Once we were squeaky clean, I was ready for more so I took his soft cock into my mouth.
The most important thing about anal sex is your lover. Trust that they will stop if you ask them too.

Use lots of lubricant and take it slow at first. There is usually a searing pain at first and it quickly evolves into lurid desire and wanton lust.

The majority of the nerve endings are at the sphincter and that is where your will receive the greatest pleasure. The long plunging strokes are just your asshole jacking off your lover.
Let you lover come in your ass. The sensation of feeling his hot come in your ass can make you come.

Above all if, you do not enjoy having a dick in your ass then STOP.
For me I overcame my fears and found that anal sex is fucking awesome, for me, with the right person. I do not have anal sex on a regular basis but rather on special times, like taking your anal cherry. Would so love to drill your pretty ass and to be your teacher!

Probingly Yours,
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