Cumming to Terms with Her Pt. 01

My first experience of anal intercourse was a pretty traumatic one.

I had been dating my girlfriend for about 6 months, and we had yet to consummate our relationship. Being a horny 21 year old man I was gagging for it. Don't get me wrong we had fooled around with oral play, and mutual masturbation. But I was 21 and still a virgin; the term "Blue Balls" didn't do it justice.

Kerry (name changed to protect the innocent) had three sisters, and each of them had children out of wedlock and two of them before they had reached their twenties. Kerry was adamant that she would not continue this less than prestigious family tradition. Despite being on the pill, my penis and her vagina would never meet.

One evening I was giving her a naked back massage, we were both covered in baby oil and I had begun to use her pert little ass cheeks to masturbate myself with, this was a pretty normal thing for us now. Sometimes she pushed back a little, just to show that she wasn't totally disgusted by me using her in this manner.

Somehow my inward thrust met her backward thrust and I felt a tightness around my cock that I had never experienced before.

Then came the screaming. To be honest I'm not overly well endowed and I would be lying if I said I had penetrated her by more than a few centimetres but it hurt her. She made me promise never to try it again, as if I meant it (come on I really didn't). So that meant the end of the last sexual act that she tolerated which still got me off.

So onanism was my only source and relief, and she considered this cheating!

I know there are other options, but when she was sixteen she dislocated her jaw so her oral ministrations where limited, and she was 21 with lovely pert a cup boobs that I loved to play with unfortunately weren't enough to wrap around my cock for a "diddy ride".

If I am honest I was considering my options. I loved Kerry but I was 21, in my prime. I was at university and I was pretty handsome so I was attracting some attention.

Options considered, I realised that if I wanted to lose my virginity I had 4 choices:

1 Leave Kerry and hook up with someone more morally ambiguous

2 Marry Kerry and finally have my way with her

3 Cheat on Kerry

4 Get Kerry drunk and pretty much rape her.

I was 21 and wasn't ready to marry anyone especially of the only reason for doing so was to lose my virginity? So that was a no no.

I couldn't do option 3 or 4 because I am not a monster or a cunt.

So decision made. I was going to break my girlfriend's heart. Looking back in hindsight, I realise that this was the best thing I could have done. Although my reasons for doing it were reprehensible, she and I were never really suited. Her now ex-husband has told me that their sex life was dull and boring. Missionary sex was the only position she would entertain, and only if she had had a couple of glasses of wine and the lights were out.

When her childhood friend came out as a lesbian, she distanced herself from her because of her conservative Christian beliefs. Imagine if she found out that I was a bisexual crossdresser? Mind blown I would imagine.

But when to do it?

The next Friday was Alan and Melissa's wedding, I was a groomsman and Kerry was a bridesmaid so it would be best to leave it until after the wedding. A week later was the Halloween fancy dress ball in the student union.

Break up with Kerry the day after the wedding so that I would have some time to get over it and go to the ball to try and charm a harlot.

Melissa and Alan were how Kerry and I met. Mel had always been one of my best friends (She had the dirtiest minds I have ever known) and Alan and Kerry went to school together. It was whilst dancing with the happy bride, that she told me that everyone was expecting me to propose to Kerry before the end of the evening's festivities. I confided in Mel as I always have, that I was intending to break up with Kerry.

Melissa almost seemed delighted with this news, turns out she never really liked Kerry and I together. When I told her why I was doing this dreadful deed. She smiled one of her dirty smiles and said in her big Northern Ireland accent.

"Your getting your hole the nite big boy." And that was it. Until Kerry and I were going to bed.

Kerry had seemed nervous throughout all of the evening shenanigans. I wondered if she was expecting me to drop to one knee in an exaggerated gesture of young love. She never seemed disappointed when the proposal didn't happen.

When I came out of the bathroom, Kerry had stripped naked and was lying on her belly with her sexy little ass in the air. She had a marvellous bottom.

"Oh yea, what's this?" my cock said as it sprung to life. All I managed was to say was

"you're naked?" In the months we had been together I had seen her naked 3 or 4 times.

"I was speaking to Alan. He is worried that you will leave me if we don't start having sex."

"I guess we were wrong about Alan. We need to buy him a drink" My dick said. Nervously I tried to reassure her, all the while my cock was saying "Don't fuck this up!" eventually I changed tact. "What about getting pregnant?" she mumbled something into the pillow that I didn't quite hear. So I asked her to repeat it.

"If you use my bum, and don't cum inside me, I won't get pregnant." My cock and I simultaneously said "Your bum?" she nodded in what she probably thought was a cum to bed look, but it was really the same drunken expression you give the kebab shop guy when he asks if you want salad. I didn't want salad, but I did want to have sex.

"But last time you said it hurt!" I asked my cock started screaming "shut up, Shut up, SHUT UP!"

"If we go slow it will be ok." My cock and his male voice choir broke into song "hallelujah!"

"What about lube?" "Do you want to die a virgin" was the chorus to the cock choir's song.

"We don't have any, but use spit and go slow." This is it!

I spent the next few minutes licking my girlfriend's rosebud. I had done this before, I got it nice and wet and moved my mouth and tongue to her pussy and clit and slid a finger into her bum. Gently fingering her ass; one finger became two and then three. I was sucking her clit watching as her tummy muscles began to contract her orgasm approached, I decided that as she climaxed I would lose my virginity.

As her orgasm washed over her, she rolled back onto her belly and pushed herself upon to all fours. I kept fingering her for a little while, continuously adding spit to them to keep her moist. She reached around and spread her lovely cheeks apart, and it was time. I withdrew my fingers, and clumsily aimed my little penis at her opening. One last coat of saliva and I pressed the tip of my cock at entrance of her asshole. Slowly I edged forward.

I knew she wasn't enjoying it, and deep down I knew that I wasn't enjoying it either. But I was a quarter of an inch into losing my virginity. She was grunting for all she was worth, I asked her if she was ok she assured me that she was. Soon a half inch of my cock had penetrated her, it wasn't long before I was half of the way in. It felt like her ass had teeth, if it was hurting me this much I was sure that she wasn't enjoying it. So I started to pull out of her, she must have sensed my hesitation and yelled "For fuck sake just do it already."

I don't know why this pissed off with her, but it did. I slammed home with all my might. I managed to pound into her a few times before it dawned on me that neither of us was enjoying this. So I pulled out of her completely. Only then did I notice the carnage that had befouled us. My dick was coated in a mixture of blood and shit. It was disgusting, and we were both sickened by it. She bleed for hours, as did I. I had a little tare in my foreskin.

The conversation that I had planned for another time, came early. A few hours later when I got into the taxi a newly single man, with a questionable virginity, I felt as if a great weight had been lifted from my shoulders.

I wouldn't be having butt sex again for a long time... well at least 6 days.