Anal

I was sitting on the sofa, next to Jenny, and having a good chat with her. We had been friends since school and were awfully close. Closer than most schoolgirl friendships were. Back in high school, Jenny and I had fucked several times while we experimented with our sexuality.

She eventually decided she was straight, while I sat on the fence until I was in my twenties. Then I ended up falling in love with a wonderful woman and eventually moved in with her.

That being said. Jenny and I remained in contact and had an awesome friendship. I had been a bridesmaid at her wedding and was godmother to her son.

Our conversation was very frank and about her husband. We had discussed the topic several times over the last couple of years.

“I’m not sure it’s a good idea. Tiffany and I have extremely strict rules regarding married people.” I said to Jenny.

She had been asking for the same thing for quite some time and my answer had always been the same.

“I don’t see the problem Felicity. You and Tiffany have an open relationship when it comes to sex. Bill wants anal and I hate the idea of anything going up there. You love anal.” She argued with a frustrated sigh.

I shook my head.

“My sexual activities broke up one marriage Jenny. I would hate myself forever if it caused something bad in yours.” I told her.

“It won’t. I promise. I’m not the jealous type.” She said desperately. “Please… Please ask Tiffany for permission.” She begged. Knowing that I did not do anything without Tiffany’s say so.

I was holding something back. I had already asked Tiffany the last time Jenny had begged me to let Bill fuck me up the ass. She had said yes but that it had to be my decision since Jenny and I went so far back as friends.

“I did ask.” I told my friend.

Jenny blinked in surprise. She had probably thought I hadn’t discussed her request with Tiffany.

“What did she say?” Jenny asked me after a brief pause.

I explained Tiffany’s reasoning and that it had to be up to me and that I still felt it could all go horribly wrong. Sex without emotion is exceedingly difficult to do and emotions can cause all kinds of problems.

At twenty-eight. I had learnt the hard way that what I liked to do could and did impact other people’s relationships.

Being a ‘conscientious slut’ was how Tiffany described it. With approval.

“Please Felicity. Say yes. It’s his biggest fantasy and I want to make sure he does it with someone I can trust.” She begged. Almost pathetically desperate.

“Why do you say that? Has he said he’s looking to do it with someone else?” I replied in concern.

Jenny bit her lower lip and then nodded slowly.

“He suggested we hire a professional… you know… a call girl.” She told me with a frightened look in her eyes.

To me, it sounded like a decent suggestion, but that is me. I have never had any problem with working girls. I did it myself for a short time to pay my Uni fees.

For Jenny, it was not an option unless she was really pushed. She did not see call girls the same way I did. It was one secret that I had kept from her. That I had taken money for sex in my late teens and early twenties.

I knew that Bill’s idea would drive Jenny insane. She took her marriage vows seriously and had only turned to me because she trusted me so deeply.

“Would that really be so bad?” I still asked, even though I thought I knew what she would say.

“God yes. I wouldn’t be able to look at him the same. Knowing he had soiled himself with some cheap whore.” She replied hotly.

I nodded in understanding and then stood. Picking up my glass of wine, I walked to the large window and looked out gaziantep escort at her garden.

Jenny followed and stood next to me without saying anything. She knew I was thinking.

I sipped my wine and gazed outward while reflecting inwardly.

“Where and when?” I eventually said softly.

“Here. In our bed… and I have to watch.” She replied quickly and then held her breath. She had never mentioned watching before.

I was not fazed by the notion of her watching. I had guessed that she would want to be a part of it.

I looked into her large brown eyes and nodded once. “Fine… when?”

She met my eyes and gave an apologetic half smile. “I hadn’t thought about that… tonight? He will be home by six?” she told me.

I snorted a small laugh at how eager she was to have it over and done with.

“Have you considered he might want to do it again?” I asked ruefully.

Jenny surprised me with her reply. “That’s why it has to be you.”

My mouth formed a small O shape and I blinked twice as I realized what she was saying.

“Exactly how often do you expect me to do it?” I asked with a frown.

She shrugged. “Until he works this little deviation out of his system I guess.” She explained. “That is okay? Right?… I mean you have had regular guys in your love life before.”

“Well. Yes. but not my best friend’s husband.” I said and shook my head. Annoyed that she had not explained this expectation earlier in our discussions.

“You can’t back out now Felicity. Please.” She sounded worried and apologetic at the same time. she knew I was a little annoyed.

“I’m not backing out. I said I will do it… But I might not do it again… understand?” I said firmly.

“Yes… Yes.” she agreed immediately.

We both looked back out the window and sipped our wine.

Out of the corner of my eye. I could see her smirking. She knew me too well and knew that I would do it as often as she asked me to. Now that I had agreed.

“You are a bad friend.” I whispered with a scowl that she recognized as not being serious.

“I’m your best friend.” She giggled back and bumped her shoulder to mine.

***

It was seven in the evening. Bill sat at the dining table with Jenny and me. He was used to me coming over often and happily poured me another glass of wine while Jenny cleared the plates.

“I guess you’re not staying over tonight then?” he said with a grin. Gesturing at me. Indicating the way that I was dressed. “Who’s the lucky guy… or girl?”

Bill was aware of how Tiffany and I worked. He often joked about it or asked who I was seeing.

I twirled a lock of my ginger hair around my finger as I coyly smiled at him. He was a well-built man with grey eyes and sandy colored hair. Good looking if you liked muscular men with a square jaw and a bit of stubble.

“Maybe it’s your lucky night.” I teased and winked at him. Shifting on my chair to cross my legs. Letting the slit in my dress show off the tops of my black stockings.

Bill laughed and grinned at me.

“If I wasn’t married to Jenny…. Ha. Ha. I’d bang you all night.” He replied and shared a smile with his wife. He had said things like that before and knew Jenny did not mind. Like she had said, she was rarely jealous, and never thought of me as a threat.

Jenny sauntered over and put her arms around his neck. She kissed him on the temple and looked me in the eyes as she spoke.

“Felicity isn’t joking darling. She’s agreed to do the thing I won’t.” she told him.

Bill began to laugh at the joke. Thinking we were playing with him.

I kept my eyes on his as I got to my feet, reached behind my neck, and undid the escort bayan clasp of my dress. His eyes went wide with shock as the dress slid down my body and pooled around my feet in a soft rustle of falling material.

All I had on was the stockings and suspenders, high heels and my jewelry.

Bill had never seen me unclothed. I will admit that showing him my body gave me a thrill. His eyes roved over my nudity. Taking in my D sized tits, slim waist, neatly trimmed ginger pubes and shaved pussy lips. He licked his lips nervously while his eyes flicked from my pale breasts to my bright ginger triangle.

“Holy shit.” He whispered in a shocked tone.

I smiled as I turned to display my rear. I was aware of how great my bum looked when framed by the black suspender belt and black stockings.

“I believe this is what you want.” I said huskily as I bent slightly to give him a good view of my backside, thigh gap and jeweled butt plug. Looking over my shoulder. I saw him nod dumbly.

Jenny stroked his sandy hair and kissed his cheek.

“This is a gift. Felicity’s bum is all yours tonight honey. But her pussy is a no-go area.” Jenny told him firmly.

Bill shook his head as if to clear it.

“You are being serious. I never thought you would say yes.” he said to his wife in a disbelieving tone.

“Well… I’m never going to let you do that to me and I won’t have you paying for it… Flic is my best friend and I can trust her.” She explained her reasoning.

Bill stood and took both of Jenny’s hands in his. He looked down into her brown eyes with intense love.

“Thank you. I love you so much.” He told her with deep sincerity.

Jenny smiled up at him and then at me.

“Let us go upstairs. Together.” She said softly.

Bill nodded and held out a hand to me. I took it and let him lead me and Jenny up to the bedroom.

Their large bed looked inviting and I crawled onto it. I did not look back as I lay my head on the pillow and raised my bum high into the air.

“Are you going to watch?” Bill asked Jenny as he began to undress.

“It would be weird if I didn’t… don’t you think?” she replied as she sat on the bed and patted my rear. Rubbed her hand over my buttocks and then flicked the jewel of my butt plug. Making me giggle.

“Yeah. I guess so.” He said as he got on the bed behind me.

I felt him caress my ass and could imagine the smile on his face.

“Your ass is amazing Flic.” He said in an awed whisper. As he massaged it and then hooked his fingers under the base of my plug.

I stayed silent as he tugged on the plug in an experimental way.

“Does that hurt?” he asked. Clearly a man that had never done any ass play before.

“No Bill. You can tweak it around a bit without hurting me… if you want to.” I told him with a small laugh.

I could hear his breathing quicken as he did as I suggested. I felt the plug being twisted inside of me and then wiggled around. He seemed fascinated as he pulled it upwards and made my ring bulge a bit before letting go and then doing it again.

There was no rush and I let him remove it an put it back in a few times.

“Use a bit of lube each time.” I instructed to make sure I was ready for when his cock went in.

Bill complied and then decided he wanted to feel around inside me.

“Umm.” I moaned as I felt him slide two fingers into my bum hole. He went slow at first. Exploring with his well lubricated fingers. Delving deeper and deeper until he was knuckle deep and making a circular motion inside me.

“What does it feel like?” asked Jenny.

“Soft. Warm. Tight yet like I could get more in.” Bill answered.

“Not you.” She laughed out as she put her face next to mine and looked into my eyes. “you.”

“Familiar. Comfortable in a way… very naughty.” I told her as her husband continued to finger fuck my anus.

Jenny nodded in understanding. “You always were a bit of a dirty bitch at school.” She said with a giggle.

I grinned at her and winked.

“Trevor Daniels and Steve May.” I replied. Jenny blushed and glared at me. It had been her who had had the first threesome out of us.

“Who are they?” asked Bill.

“No one you know darling. You know how Flic is.” Jenny replied quickly. Making it sound like those boys were part of my past and not hers.

“Yeah… and now I’m getting a turn.” Bill replied excitedly as he removed his fingers and positioned his cock.

I felt the tip push against my back door and let out a gasp of anticipation.

Jenny sat up to watch as Bill slid the head of his cock into my ass. Stretching it wider than I had expected and making me wince a little.

“You okay?” he asked as soon as he felt me tense up.

“Yeah. I’m good… go slow at first.” I replied breathily. Now enjoying the sensation as I relaxed. His cock was big and thick. Now that my bum hole was snuggly stretched around his shaft. I knew what I was getting.

With both hands on my hips. Bill began to work his cock in a slow rocking motion. Easing more and more of it into me. I was tempted to reach for my clit but held back. My pleasure had to be secondary to keep this about Bill and Jenny.

I found myself moaning and blinking in amazement as he fed me inch after inch of his stiff cock. I realized that he must be at least nine inches long. Which was a lot for me. I am only five two and had rarely had anything that big in my rear.

I felt his hips press against my tushy and gave a gasp. Part pain and part pleasure.

Bill was gentle and steady as he pulled halfway out and then pushed back in slowly.

“This feels so good.” He whispered.

“It… it looks so wrong.” Jenny said. Not really talking to either Bill or me.

“Ung.” … “Ahh.” … “Unnggg.” Was forced from my mouth in short gasps as Bill began to thrust a bit harder. Hard enough to make soft slapping noises when his hips banged against my buttocks.

“Oh fuck. Oh fuck.” He panted out in pleasure as he worked harder and faster. His balls swung and slapped against my shaved pussy lips. They would stick there for a split second. Glued by my sopping wet cunt.

Jenny watched in silence as her husband pounded my ass in fast relentless strokes. The room filled with the noise of flesh on flesh. My yelps and Bill’s breathy swearing.

“Ffffuuuuuucccckkkkk.” Bill grunted out suddenly as he slammed all the way inside of me and held himself balls deep in my ass.

I felt him judder and his cock twitch inside me as he began to ejaculate.

Again, I was surprised, as Bill spurted again and again. Filling my anal canal with his semen. His unloading seemed to last forever as his body shook and made my butt cheeks tremble.

With a tired sigh of pleasure. Bill pulled out of my ass and used his hands to hold my buttocks apart. I guessed that he was looking into my gaping hole and enjoying the sight of his cum slicking my innards.

“Jenny. Do you wanna see?” he asked in almost childish delight. Wanting to show off.

I felt Jenny move.

“That is…. A bit sick darling.” She said as she peered into my hole. A hole that was beginning to close.

“I wanna do it again. Can I do it again?” he asked eagerly.

I turned over and looked at them both. Jenny shrugged and looked at me.

I rolled my eyes. “Okay. When you get it up again?” I agreed.

Bill began to stroke his cock and grinned. “be ready in a jiffy.”

I wiped sweat from my brow and shared a look with Jenny. It was going to be a long night and we both knew it.