The Taking of Pamela’s Anal Cherry

By DarkSide

Original link:

Tags: anal, bi-sexual, oral, threesomes

Added: 10 Nov 2012 Views: 28864 Avg Score: 4.94

Lesley, my wife and Pamela were bi-sexual friends, but their relationship was about to change.
Lesley is my wife, she is a self confessed raving bi-sexual, in fact if we hadn’t been married I think she would have been a raving lesbian. Sex was always high on Lesley’s mind. Because of this we started to experiment early on in our relationship. Firstly it was with other men, then it progressed to couples and eventually we found ourselves entering the swinging scene. It was total sexual liberation for me and for her.

We both loved nothing more than to see each other give and receive pleasure from whichever source that seemed to come from. More often than not, Lesley always found herself between some woman’s thighs and loving every minute of it. I also loved every minute of watching her as well.

Lesley’s friend is Pamela. We had known that Pamela had also experimented sexually. In fact it was a long time after we were married that Lesley said that she actually fancied Pamela and would love to lick her senseless. Well, that actually came to pass not so long ago. Six months ago in fact, when the pair of them found themselves on a girlie holiday for five days while I was left at home working.

I knew Lesley would try it on with Pamela given the opportunity, and although Pamela knew nothing about our sexual openness and our involvement in the swinging scene, I knew that Lesley would turn the conversation around to sex eventually. She did just that, but it did take her a long three days to do it.

That was how Lesley and Pamela started to become sexual friends. They came back from holiday with the broadest smiles on their faces and told me absolutely nothing of what went on, apart from them having a great time.

The first I knew of what happened on that fateful holiday, was when Pamela and Lesley barged through our door after a night out, they were drunk, and kissing each other all the way into the lounge where I was watching the Television.

My jaw dropped, as I saw them openly kissing each other. Then as suddenly as it started, the giggling stopped and they turned to look at me sitting on the sofa.

“Are you joining us, or staying there…” asked Lesley, the words slurred out of her mouth as she grinned at me.

Pamela sat down next to me and placed her hand on my thigh and within seconds it was sliding up to my crotch. She was looking and smiling at Lesley as she did it, presumably looking for confirmation that she could do what she liked.

Lesley just smiled back.

“Come on you two…” she retorted, “we have some fucking to do!”

That was the first time that the three of us got together and what a night it was. I was in heaven seeing the both of them together for the first time. Lesley was more than happy. Pamela was not just another girl that was picked up at the local sex club. She was a friend, and the sex between them was all the more special for it.

Since that night we have had threesomes practically every weekend and even once or twice in the week as well. You could say we have become a kind of husband, wife and girlfriend as Pamela practically lives with us now. I am not complaining one little bit.

It was on one of our Saturday nights in, when events changed Lesley’s and Pamela’s relationship for good.

The sex we had was always confined to female oral, licking and sucking with me being the fortunate member to fuck both women during the course of the evening. Yes, the odd toy was used now and then and there was an awful lot of orgasms experienced by the girls, but the only real penetration was performed by my cock, and if I am to be honest, it was more than a challenge for me to keep up sometimes.

I entered the bedroom a little later than I normal that evening to find that Lesley’s arse was poking into the air in the most gorgeous way ever. She was between Pamela’s thighs and eagerly licking her pussy and stroking her thighs as she did. Pamela was half reclined on the bed, eyes closed and enjoying the licking. No-one seemed to be desperately close to orgasm yet, but Lesley was mewling away as she licked ever more intently.

I decided that Lesley’s arse was too good to pass by. I left the room and decided to oil my cock liberally in the bathroom. As I did, I imagined slipping into Lesley from behind as she licked her friend. I had done this many times, but it was going to be her arse this time.

My cock stiffened in an instant at the thought. I re-entered the bedroom to find the two girls in the same position. Pamela was now moaning a little and grasping at Lesley’s hair every now and then. She opened her eyes as I entered the room.

Pamela smiled at me as I positioned my cock over Lesley’s anus. I started to push and I felt her little hole give way to my oiled cock. I smiled as I entered her and I heard Lesley gasp into Pamela’s pussy.

Lesley lifted her head from Pamela‘s cunt and looked up at her with half closed eyes.

“Fuck…I love it up my arse…” she said looking directly into Pamela’s eyes.

Pamela immediately looked at me, and then back at Lesley.

“Is it going up your arse?” she asked.

Lesley nodded, “fuck, yes…” she replied.

She then returned to lick Pamela’s pussy. This time it was more urgent. She lifted Pamela’s arse off the bed with one hand as best she could and drew her tongue the length of her cunt before it rested on her clit. Lesley performed the same action several times. I knew her eyes would be half closed throughout her pussy licking as she always savoured being fucked in her arse.

Pamela started to buck a little into Lesley’s mouth as she moved her hips upwards off the bed. She kept looking at me and then at Lesley. She was gritting her teeth as she felt Lesley’s tongue lick and suck on her clit.

“Finger my arse too…”, the words came out of nowhere.

It took me a few precious seconds to realise that they came from Pamela.

Lesley looked up at her friend not believing she had heard what she thought she had heard.

“Finger my arse, Lesley.”

Those words definitely came from Pamela, I was watching her say them as she stared into Lesley’s eyes.

“Are you sure?” Lesley asked.

I heard the excitement in Lesley’s voice and when I saw Pamela shake her head yes, I could see the joy in Lesley’s face.

“Get me some oil, please.” Lesley looked over her shoulder at me. I just nodded and slipped my cock from her arse and fetched the oil.

I returned and tipped the oil onto Lesley’s hand. She immediately smothered it all over Pamela’s pussy and let it flow onto her anus.

I sat back on the chair opposite the pair of them and decided to watch instead of complicating the situation.

Lesley pushed her finger towards Pamela’s anus, she twisted and pushed it against her tight hole until it gave in, and her finger slipped inside. Lesley held it steady at her first digit savouring the tightness around her finger. Pamela was breathing heavily and staring intently at Lesley’s progress.

“Go on fuck your finger into me…”, her words were base.

Lesley looked once more into her eyes and then shoved her finger up into Pamela’s arse, centimetre by centimetre. Each time removing it and then shoving it up further.

It wasn’t long before Lesley was openly finger fucking Pamela’s arse.

“Yeah…”, nodded Lesley.

Pamela just nodded back in her direction. Then turned her head slightly to face me as she smiled.

“Fuck me….yesssss,” cried Pamela as Lesley’s mouth urgently sucked on her clit. Her middle finger was now buried in Pamela’s arse and Lesley was sucking on her pussy and clit.

Once again Lesley’s arse was raised in the air as she lifted her legs up the bed. As she rested on one hand the other pumped her finger into and out of Pamela’s arse. She started to lick urgently, her tongue was a blur on Pamela’s clit and she knew that she would not last long under the onslaught of sensations.

Pamela cried her orgasm out into the room with so much volume that I thought she was being hurt. She was pumping her pussy up to meet Lesley’s mouth and tongue or was it to meet her finger thrusts. I don’t think she cared, she just wanted to cum, and cum hard.

Pamela’s orgasm just about caused Lesley to lose her balance and fall sideways on the bed. Lesley suddenly stopped her oral ministrations as Pamela heaved herself from her face. Lesley’s finger was forcefully removed from Pamela’s anus and Lesley eventually sat up on the bed watching her friend orgasm.

It was an orgasm that Lesley, nor I, had ever seen before.

I could see that Lesley’s face was contorted with lust. She was dying to get back in there and lick and finger Pamela some more.

Pamela was eventually nearing recovery, her breathing was returning to normal when words came out of Lesley’s mouth that would change their sexual habits for good.

“I want to fuck you up the arse…”, said Lesley, “please, Pamela, can I fuck your arse?”

Pamela looked at Lelsey, then me, then back at Lesley. She nodded.

“Yes, yes please,” she replied.

Lesley jumped off the bed as quick as ever, she reached into her bottom drawer and pulled out her slimmest dildo and firmest strapon that she owned.

Like I said before, Lesley loved sex, she also loved to fuck when the opportunity presented itself. She had fucked other women before, many times, and I knew that when she did she became worse than a male fucking machine on heat. She was worse than any man could be - lust raged inside her when she was doing the penetrating. All of a sudden, I started to fear for Pamela’s well being.

Lesley had strapped her leather strapon to herself in record time and was now sporting a pink hard-on. It was a thin hard-on and only about six inches long but it wasn’t the size that mattered it was what she was like using it, and Pamela was about to find out.

Lesley started to oil the dildo strutting from her crotch and wanked it as proudly as any man would wank his cock.

Pamela moved around to the centre of the bed and with hands on the bedstead, she waited on all fours for the penetration of solid female cock.

I was, of course, loving every minute of the spectacle before me.

I shook my head as Lesley knelt on the bed and positioned her cock at Pamela’s forbidden entrance.

With a great deal of excitement in her voice, Lesley asked for the last time.

“Are you sure you want this Pamela?”

Pamela looked over her shoulder, studied Lelsey for a while and without remorse replied.

“Fuck me in the arse…and fuck me good…”

Lesley inched her cock into Pamela. It was difficult at first, then suddenly it slipped past the sphincter. Lesley held it there for a while, allowing Pamela to feel the girth of the penetration in her arse.

Pamela started to buck her arse backwards a little as encouragement.

Lesley started to grin as she fucked the cock further and further into her.

When it was all the way up, Lesley withdrew it almost out of Pamela completely and then shoved it back in.

Pamela gasped loudly as she stared at the wall, her mouth open, and her arms absorbing Lesley’s thrusts.

Then I saw the change. I knew it would happen. Lesley had looked on her friend as her cock had entered her, but now she was looking at the fuck of her life. Pamela wasn’t any other woman she was her best friend.

I saw Lesley’s eyes fill with lust, I watched her breathing increase, I watched her stare at Pamela’s arse as she fucked into it. Without much conscious thought, Lesley’s hands grasped Pamela’s hips and she started to pull her backwards in rhythm to her forward thrusting.

“Oh fuck, yes…” cried Pamela.

It was all the encouragement Lesley needed.

“Fuck…Fuck…Fuck…”, Lesley was now chanting the words with every thrust, and the words were coming faster and faster.

To my astonishment, Pamela was also pumping her arse back towards Lesley. I had seen Lesley fuck other women with her strapon, but this was something else. Pamela was being more than an active participant and Lesley was now pounding her arse like a rampant bull.

Lesley was fucking her friend for all she was worth, as good as any man could have done and with such energy. Then she reached out and grabbed Pamela’s hair and pulled her head backwards as she fucked into her from behind.

Pamela screamed out in what I thought was pain, but before I even realised it, Pamela was screaming with pleasure.

“Oh Fuck…yesssss…fuck me, fuck my arse…”, she kept saying, over and over.

Lesley fucked her pink cock into Pamela with gritted teeth.

Finally Pamela’s orgasm ripped through her and she started to collapse on the bed. Lesley was not letting up. With Pamela’s head in the pillows and her arse pointing upwards, Lesley thrust he cock into her relentlessly.

I think Pamela had about three orgasms on that bed with Lesley fucking into her. Eventually Lesley fell backwards and her pink cock fell from Pamela’s arse.

Lesley sat back on her thighs as she looked at Pamela completely prostrate on the bed, satisfied and sated and breathing heavily.

Pamela eventually got up and turned to face Lesley. They kissed, passionately.

Pamela then turned to look at me, she smiled, worked her way to the edge of the bed and lifted her arse in the air.

“Fuck my arse again…please?” she asked.

I immediately stopped wanking, sprung up form the chair, and immediately started to plunder Pamela’s rear entrance. Fuck it was wonderful to fuck her up her arse.

I watched Lesley as she removed her strapon. She sidled up to Pamela and they started kissing. Lesley eventually moved around to put her arse on the edge of the bed next to Pamela’s.

“My arse too…” she said, matter of factly.

I shook my head as I removed my cock from one arse and thrust it up my wife’s. It wasn’t long before I was alternating between Pamela’s and Lesley’s arse as I fucked them both.

I eventually came in Pamela’s arse. I thought it would give Lesley something to look forward to in the night to come. As I removed my cock, she immediately pounced on Pamela’s arse and licked her hole to try and tease my spunk out from inside.

The girls eventually started giggling. This was an act that I always found strange. So I just shook my head and walked to the bathroom to wash my cock. After all, the night was young.