Try Everything Twice

Anal sex taught me a valuable lesson: always try everything twice. My first experience had been disastrous. I was nineteen; he was only my second lover and I was head over heels. There was nothing I would not do for this man. So when he wanted to try anal, I conceded.

But since he had no experience in anal and I had little sexual experience period, we made several mistakes. The first major mistake was not to use any lube; other than his cum which was leaking from my fresh fucked pussy. Another mistake was the position; woman on top is less ideal for anal penetration, especially the first time. In addition, my lover was definitely on the large side; almost eight thick inches, hardly a good size for a first timer. Traumatic does not begin to describe the whole experience as I ended up crying through intense pain.

After such a horrid beginning, I swore never again. During my fourteen year marriage, it was almost a weekly plea from my former husband who definitely had an anal fixation. He would beg and plead often, 'Please, I want to fuck your ass.' But I was adamant; I would never try anal sex again.

Then after several bitter and sexually repressed years, my marriage ended. I entered a new and brief period of sexual re-discovery. I dated and had sex with dozens of men. I tired things I had only imagined; including swinging, bondage and submission. Yet still I was held fast to my 'no' anal motto.

Until I met T. He was funny, sweet and handsome. We became lovers on our first date. And I admit it, I was disappointed this guy had one of the smallest penises I had ever seen; not only in length but in girth as well. The wonderful thing about him though was that he was comfortable with his 'short cummins' as he called it. He also was excellent lover in terms of orally pleasing his partners.

We continued to see each other on and off for a couple of months. This is the story of one wonderful weekend day and my sexual discovery of the joys of anal sex.

His son was with his ex-wife for the weekend, so he invited to his home. He greeted me at the door with a soft kiss on the lips. He had prepared a nice lunch, which we shared over a glass of wine as we discussed our weeks. All of this reminded me of why I enjoyed this man company so very much.

As we refilled our glasses with more white wine, we moved into the bedroom. T said he had something to show me. When he opened a drawer in the night stand, my eyes flew open wide. It was full of toys; sex toys, vibrators, dildos, pocket rockets. Most impressive was a heavy duty, electric powered vibrator that boasted more pleasure than anything my battery-operated toys could ever achieve.

As we got naked and fell laughing onto the bed, he began a slow experimentation with my responsive body. He had me describe in detail how each felt as he rubbed it against my sensitive clitoris or pushed it deep into my wet cunt. He kept me on the edge of a powerful orgasm for a long time.

When he knew I could not last much longer he donned a condom and entered my soaking wet pussy. He fucked me as hard and deep as he possibly could as he held that powerful monster of a vibrator to my throbbing clit. By the time, I came with a scream; he was sweating above my trembling body.

With a laugh, he rolled to the side. 'That is why I have so many toys,' he explained. We drank another glass of wine as we laughed and talked some more; waiting for him to recover for the next round. Somehow the subject of anal sex came up. I related my bad first experience and my determination to never try it again.

Whether it was the wine, which I was definitely feeling a buzz by this time, or his playful persuasion that I had simply done it all wrong the first time, or the fact that his penis was so much more appropriate for this task than my previous lover, by the time he had recovered and was sporting a new erection he had convinced me to give anal one more try.

T arranged pillows at the bottom of the bed. He had me leaning across them so that my soft bottom was gently lifted into the perfect position for penetration. He poured a generous amount of the warm and tingly lubricant which he had used with the toys over my tiny brown hole. I could even feel the warmth seeping down into my recently fucked cunt.

Then T reached over and grabbed that amazing toy, 'Hold this to your clit,' he commanded. Once I had placed the buzzing wand between my legs as instructed, he turned the controls to its lowest setting so that a gentle but constant stimulation was present on my sensitive love bud. He rubbed his hands slowly across my shoulders in a tender massage until I relaxed into his touch.

Slowly his hands moved lower until he was more firmly kneading the round globes of my untanned ass. Between the massage and the buzzing on my tender clitoris, I was most definitely aroused at this point. My breasts were pressed against cool cotton sheets; my nipples painfully aroused as they brushed back and forth with each tiny movement of my aroused body.

Only then did my lover slip his finger slowly into my ass. He was extremely gentle; tentative almost as he teased the edges of my asshole with slow circular outlines which became smaller and smaller as they approached the bull's eye. Then pushing forward with steady, firm pressure he violated my secret passage; pushing an inch or so into my tender bottom before slowly retreating. He repeated the process over and over again; advancing a small fraction of an inch into my almost virgin bottom with each new attempt.

He continued this process for what seemed forever as the soft buzzing of the vibrator continued to stimulate my clit. Finally I felt his finger fully embedded inside my tight ass. It actually felt surprisingly good. I relaxed a bit thinking; this isn't so bad.

T leaned forward and kissed the side of my face. With his finger still fully inside my ass, he used his other hand to turn up the speed on the toy. I jumped a tad then from this new sensation. This caused his finger to somehow slip just a fraction of an inch deeper. I could feel my body becoming even more aroused and wetter with each passing moment.

I whimpered when I felt T withdraw his finger completely from my bum. But I was not to be disappointed for long. He grabbed the bottle of lubricant; adding another generous amount to my already wet holes. 'Relax,' he commanded; as if I could as aroused as my body was at that moment.

Then he returned to his previous game of slowly circling my tender rosebud; except this time it was two fingers that I felt slipping slowly into my sweet upturned ass. I automatically tensed a bit then; feeling my body stretched, reminding me instinctively of that other time and the pain I had felt. But instead of retreating, this time T simply held both fingers steady, firmly ensconced in my bottom until I once again did begin to relax.

'Good girl,' he said as he began to steadily work his fingers back and forth inside of me. He was a tad more assertive now; as if he somehow felt my building reluctance and knew that he must overpower it with his resolve. In a matter of less than five minutes, he had successfully worked both fingers fully into me.

He once more increased the speed on the vibrator between my legs. Its buzzing now was no longer gentle, but not enough to trigger the orgasm I desperately needed. He then began to open his fingers slightly on each outward movement; as if they were a pair of scissors. This stretching burned a bit, but I recognised an edge of pleasure to the discomfort.

'Ready now,' he proclaimed; more a statement than a question. In a blur of motion, he donned another condom, turned the vibrator onto a setting that would get the job done, and squirted a liberal amount of lube once more into me. This time he used that scissors movement to stretch my hole; making certain that some of the fluid went inside my tight passage.

Before I could protest that I wasn't sure about this, he pushed his cock fully inside of me. I jumped a bit then; because even with his less austere equipment, I felt that invasion. He held firmly to the cheeks of my round bottom so that I could not evade his cock's intrusion. 'Worked that pussy with the vibrator,' he commanded firmly.

Seeing little chance of escaping this new and domineering side of my lover, I obeyed. Soon I felt my body begin to relax as the toy brought me closer and closer to the orgasm I needed desperately at that moment. Then it happened, I felt my pussy contract in a powerful release as the buzzing on my clit pushed me over.

As my orgasming pussy caused my ass to squeeze even tighter around the invading cock, T began to move then. Fucking slowly back and forth into my asshole, he growled, 'Keep working that little pussy.' He became a mad man; fucking into me quickly and roughly.

If he had been larger, I am sure that I would have torn and bled. But as it was, the combined stimulation of the vibrator, his dominance and the taboo of the situation was getting me more and more aroused. Within a couple of minutes, I found myself not only enjoy it, but actually pushing back to meet each thrust of his cock into me; trying desperately to draw him deeper still.

I had more powerful orgasms as he continued the assault on my asshole for several minutes. Then I felt he push deep and tremble above me as he filled another condom with his hot seed. T held deep inside me for a moment as I felt his sweat drip onto my ass to mingle with the lubricant. It was surprisingly cool and refreshing against my now stretched and freshly fucked ass.

I won't say that this experience turned me into some anal slut who simply cannot enjoy sex without taking a cock into her ass. But it did add another tool to my sexual toolbox. I continue to enjoy anal sex on occasion with my husband, especially when the fucking has been wild and rough. Oh, and being the victim of a bitter divorce, I was quick to pick up the phone and chide my ex-husbeast with the news of the sexual conquest of the asshole that he had coveted for fourteen years.