An Evening with Friends 03: Bi-Night

An Evening with Friends -- Part 3 - Bi-Night

Our swinging evenings so far had been fun. Both times, we had enjoyed one another, loved being together and felt our inhibitions lift.

The first time had been fairly spontaneous. I know that Emma had planned it to some extent, and that by throwing the possibility out, she had taken a slight risk. Of course, we could have said 'No', but why? We were all good looking, all open-minded, and we trusted one another. In some ways, once the idea was in our heads, taking games a bit further was natural -- and we loved it.

Our second night had been planned and directed. Emma had, again, been the driving force. Things went further this time. The suggestions of experiencing partners of the same sex, which had fallen into the category of dares on the first occasion, had been taken all the way by our wives. It was very clear that they had thoroughly enjoyed lesbianism -- and we -- the men -- had loved it too. So why was I so apprehensive about the 'Bi -- Night' proposed by Karen and Jeff?

My wife, Claire, thought I was being absurd -- and unfair.

'You know you loved watching me with Karen and Emma -- not to mention Marie. We stripped each other, played with each other's tits.'

As she spoke, Claire had pushed the covers down to expose her large, soft breasts and starting fingering her own nipples. She pinched them erect, then licked a finger. Seductively she ran her wet finger around each rigid point, leaving it shining in the soft light.

'Then we stroked each other's pussies.'

She pushed the cover right down and allowed her legs to fall apart, and her hand wandered between them, parting the moist lips there to reveal the pink within, and her most sensitive part. She began to stroke herself gently, almost absent-mindedly.

'We fucked each other with toys.'

Reaching for the drawer in her bedside table, she withdrew a transparent, cock shaped dildo, probably the same length as my own penis, which was now very erect thanks to her teasing performance and the memories it was stirring.

She was as stimulated as I was, and when she placed the tip of her sex toy against her vagina, it slipped inside easily. She knew how much I enjoyed this particular toy. Not only was it utterly smooth and similar to my own cock, but it was made of transparent acrylic, and if I shone a torch on it when it was inside her, I could see every detail of her passage. It made for fascinating photographs -- especially with a flash.

I reached across for her, eager to play my part in her reminiscences, and to put my rock hard cock to good use.

'No!' She pushed me away. 'I'm remembering girl-time.'

She continued her trip down memory lane as I watched her masturbating, and wondering what she was leading up to.

'We licked each other and put things in each others' asses.'

Obviously, even though she was flexible, licking herself was out of the question, and she had made it clear that my tongue was not welcome on this occasion. As an alternative, she gazed into my eyes and licked the fingers, which so recently stroked her wet cunt, then reached into her drawer again and took out a butt plug. Placing it on the bed while she retrieved a tube of lubricant, skilfully removed the lid with one hand and applied it to her anal toy, before lifting her buttocks and inserting it between them.

'Mmmm...' she closed her eyes and groaned, breathing more heavily now.

'We fucked each other and we had explosive orgasms.'

She was building up a good rhythm with the dildo, ensuring that, as it was inserted to its fullest extent, her hand brushed the sensitive little button which was helping her towards her climax.

She stopped talking now, focused on bringing herself to orgasm, knowing how much I loved to watch, and how desperate I was to join in.

Suddenly, she discarded the dildo, as if bored, but in truth wanting to focus on her clit as she rubbed herself to a small, but clearly satisfying orgasm.

She lay still for a few minutes, enjoying the afterglow, before slipping out her butt plug and turning to me.

'You can stop that!' She commanded, seeing that I was stroking myself. She reached over and batted my stroking hand, slapping the end of my engorged cock.

'Ouch! What's that for?' I exclaimed.

'You!' She returned. 'Ever since bi-night was mentioned you've been off. I know you're trying to find some excuse. Stop it. You're all 'I'm open-minded, no hang ups' until now. Well get over yourself! They're our friends and I trust them. You need to trust them too.'

I knew she was right, but whether it was my upbringing or whether I had some deep seated prejudice, I didn't know, but it didn't sit right with me.

'Sorry,' I mumbled, 'you're right as usual. It's not that easy though. You know what my mother was like...'

'Yes,' Claire interrupted, 'I do. But it doesn't stop you fucking my arse, cumming on my face, licking my pussy, fucking our friends and those bits of bi stuff you've done already. You're not homophobic. It's like it's fine for everyone else but not for you.'

She was right again. But still, surely something as deep seated as my fear of having another man's cock up my ass couldn't be overcome that easily. I tried to explain this to Claire.

'OK,' she flung back, 'Let's overcome your 'deep seated issues', starting now! It's not like you haven't tried anal before -- but I'm going to make you like it!'

I was astounded by her domineering attitude. Claire was not usually like this, but I could only put it down to two things -- firstly, she was becoming more sexually assertive, thanks to our new lifestyle; secondly, she was really pissed off with me. From experience, I knew she could bite back when annoyed -- but becoming sexually assertive was new, and I liked it.

'I'm going to show you a website about men and anal sex -- receiving, not giving -- and we're going to read through together.'

By now, my once hard cock was slowly deflating, and the idea of going through a website really didn't help -- but Claire's next words did.

'But before we do that, come fuck me.'

She turned on to her hands and knees, raising her gorgeous ass in the air, replacing the butt plug. Seeing that ass and the wet pussy beneath brought me twitching back to attention. I took place behind her and slipped smoothly into her well lubricated hole, loving, as I always did, the view of my cock plunging in and out.

The plug was not new, as we had done this before, and I liked it -- though her dark hole looked better.

As usual, Claire fingered herself as I fucked her, loving to have me work her g-spot, while she worked her clit. Her previous orgasm had made her sensitive, and it was not long before she climaxed again, her tight muscles squeezing my erection as she achieved satisfaction.

Usually at this point I would take advantage of her highly sensitive state and ram in and out until I released my cum deep inside her.

This time, however, rather than settling and enjoying extended ecstasy, she instructed me to stop and withdraw (her actual words were: 'Right, get the fuck out!').

Confused, and disappointed, I did as I was told.

Claire, however, much to my relief was not finished.

'Right,' she instructed, turning over and removing the butt plug in one fluid motion, 'I want you to fuck me with my legs over your shoulders. You know how to do that.'

Indeed I did. We often moved from the missionary position, to placing my arms under legs to lift them even wider and allow me to get deeper inside, to lifting her legs right up along my chest and over my shoulders, bending her at the waist and giving me space to fuck her vigorously.

'When I'm there, I want you in my ass. I'm lubed up and the plug's done its job, so you should get straight in.'

Previously, and rather uncreatively, I suppose, we had only done anal in the doggy position. This was different. It was the first time I had realised that, maybe, I had been rather uncreative.

It seemed very odd, considering how forceful Claire was being, that she had chosen such a male-dominant position, but I think maybe that was the point.

I did as instructed, and entered smoothly.

'God that's good,' breathed Claire, looking into my eyes, 'now fuck me till you cum.'

This too was new. Claire had always been willing to do anal, but would not let me ejaculate there. Something to do with it all running straight out again, I seemed to remember. Maybe she was trying something new too.

Although her anus was looser, my cock was considerably longer than the butt plug, and the tightness around my glans, and my arousal ensured that I was shooting semen into her far more quickly than I would usually want to. Claire, however, was unconcerned, and after a short time to allow my spasms to finish, she lowered her legs (to avoid cramp) and lay them flat on the bed, gently ejecting me.

I rolled off and held her gently, as we always did after making love.

I considered what to say.

'Well... that was... er... different.' I laughed and waited for her to react.

'Good different?' She asked.

'Yes.' I was confident in my reply. 'Definitely. The new position -- well -- not position -- new point of entry -- was interesting. Must have been good for me to cum so fast.'

'We've never done anal face to face before,' she pointed out, ' I needed you to know you don't have to look at an asshole to fuck one -- and if you're gonna do it, maybe it'd be more comfortable at first if you don't.'

I saw her logic and appreciated it. Maybe it would help, maybe not, but it was a starting point.

Claire sat up. 'Right. You get the laptop, I'll just go clean up -- oh -- and bring a cloth -- I leaked a little!'

We reconvened ten minutes later, and as Claire navigated her way to the web site, she explained her commitment to this particular aspect of our sex life.

'First,' she said, 'it's about fairness. Men penetrate us all the time, and think it's nothing. We like it, but it'd be nice for you to experience it sometimes. You guys tend to dominate and we can only be on top to avoid being totally covered. You should know how it feels -- in a good way. Second, we all did the girl on girl for you and you loved it. Don't you think we might enjoy seeing two guys together? Third, you will enjoy it. I know you will, but you need to know how. And I'm going to show you -- just like Emma and Karen are doing with their guys!'

'You're all doing it?' I blurted out.

'Yes,' Claire responded gently, 'apparently it's not a big deal with Dave -- he's been bi-curious for a long time, and Jeff is intrigued and going with the flow. We want to make sure it's good for all of you. This is the taboo we want to break to make us all totally trusting. Emma, Karen and I are already there -- you may have noticed --' she smiled to herself, recalling, no doubt how they had performed with one another, 'but we want you guys to share what we have. It's not a permanent thing, you're not going to become bi overnight, but it's an experience you need.'

She turned and leaned lovingly into me.

'Oh. And it'll leave us horny as fuck. Don't forget, it's bi-night, not gay night, so let's hope there's plenty of cock left for us girls!'

Claire sat up, the sheet falling away from her heavy breasts. Placing the laptop on her legs, so that I got a wonderful view of screen and her still erect nipples, I began to read through the website.

Unsurprisingly, I suppose, it was written by a gay man. However, he wrote knowledgeably and from experience, not exalting the joys of gay sex, but the pleasure available from anal sex for straight and gay alike. It was well written, and amounted to a list of techniques and how they produced pleasure. I found his style disarming and appealing. Setting aside my upbringing, where all things anal were considered 'dirty', I found myself buying in to his opinions, and looking forward to seeing if the joys he described would also happen for me.

'To my straight male brothers: Regardless if you're straight, gay, or bisexual, you can still enjoy a wonderful thing called ass play. In fact, more and more straight men are. You're not alone!'

The website had a point. I knew several men who openly admit that they like 'ass play', I suppose, if women are expected to enjoy it, and clearly do, then why not?

Plus, Claire wanted it. I am not submissive, but I do like to make my wife happy, and if something so relatively minor could please her, then I'm all for it!

The article began by talking about lubricant (phew!), and discussed sex toys - from prostate stimulators and small butt plugs to XL dildos and vibrators. It went on to consider sensitive areas, and how leaving the penis alone and stimulating anus and prostate can delay and enhance orgasm, while maintaining stimulation.

Along with the rather scientific information there were pictures of toys for the prostate, which looked small enough not to cause pain, yet sufficiently 'shaped' to carry out their intended job. I was also intrigued by the notion of 'getting to know' my body.

It concluded by stating what a good way it was to start understanding our gay 'brothers', along with an impassioned plea for straight men to give it a try so they did not miss out on a wonderful experience.

I was in! The writing was typical of someone who truly believed what they were saying, and I genuinely wanted to understand why so many men - gay and straight - enjoyed the sensations. As an active supporter of LGBT+ rights, and the Pride movement as a whole, it was an opportunity I knew I had to take,

I smiled at Claire.

'OK. When do we start?'

She returned my smile with interest.

'Tomorrow.' She skipped out of bed, deliciously naked and returned with an unlabelled plastic bag. 'I've got some toys.'

Onto the bed she tipped several items, still in their boxes or plastic packaging. The first thing I noticed was a bottle of lube. It was plain, ordinary looking. I was glad of that - if it had claimed to be some special formula, cynicism might have crept in.

There was a butt plug; one of the prostate stimulation devices, looking like a glass twig, or a knobbly witch's finger; a dildo, only about six inches, clear, and transparent, similar to the one she had used earlier. another prostate device, this time attached to a harness, presumably for her to wear; a strap-on, with what I would accept to be an average sized penis substitute and finally, what looked like a rubber ball with a long tube attached.

It was the latter which attracted me first.

'If you fill me with air down there, I'll just fart.' I joked.

She slapped my arm.

'Idiot,' she giggled, 'You fill it with water. It's to get clean.'

Once again, I was relieved. Cleanliness was important. It was less the hole itself which upset me, and far more its day to day contents. Knowing that these would be removed was, again, reassuring.

'Right,' she continued, back to her more dominant mode again, 'you know what all these are. From tomorrow, we're going to start trying them out, building up to some of my toys. That way, you'll be ready for anything!'

I wasn't sure about 'anything', but I was confident that she would prepare me for whatever our forthcoming event might throw at me.

The following evening, I was sent to shower and 'get clean'. I found the latter part of the process rather challenging. Having used lube rather liberally and filled the rubber globe with warm water, I placed it gently on my anus. It felt... I'm not sure... not unpleasant. I moved it around over the opening, and as my cock began to twitch, realised that I found it quite stimulating. Actually, it was really pleasant.

Then, very gently, I pushed. Initially, I had to change the angle a little, and then, slowly but easily, the narrow tube slid in. It felt odd, but somehow exciting. Some two inches in, I was hit with what felt like an electric shock. This must be my prostate - and although the actual entry was a little odd, this sudden thrill was well worth it.

I slipped the tube in to its fullest extent, and squeezed, filling myself with warm water. If the rest of the insertion had been a strange, but on the whole pleasant, voyage of discovery, this bit was far less pleasant. It filled me with an urgent need to defecate, and my anus clamped shut.

Removing the tube, I quickly 'assumed the position' on the toilet, before expelling the water in a forceful gush. I disliked this part, but accepted that it was essential -- no point leaving the water in there!

After completing my excretions, I went to the shower, washing thoroughly, still apprehensive at what was to come, but remembering those wonderful sensations, and fascinated by the idea of what this could mean when my wife went to work on me.

I actually felt incredibly clean, especially with the lube now washed off, and was ready to get started, unconcerned about my personal cleanliness.

Putting a robe around me, I returned to the bedroom where Claire lay, prepared for me. I approached the bed and gazed down at her, like me, clad only in a thin robe. For the millionth time, I thought how beautiful she was -- especially with the half smile which she now wore.

'I've been looking forward to this,' she grinned, 'your ass is mine!'

I shrugged and joined her on the bed. She wriggled across to me, moving close and allowing me to enjoy the faint scent on her clean skin.

'Are you a clean boy?' she asked, running her fingers playfully across my chest.

'I think so,' I assured her, 'I did exactly what you told me.

'Well,' she muttered, 'I'll soon find out.'

She moved her head across and began to kiss my chest. Her hand parted my gown, and she steadily worked her way down towards the engorged head straining up to meet her.

I had always loved having my cock sucked -- especially by Claire, who seemed to consider it her duty to perform to the highest level. She licked up and down my shaft, circling the purple head, before descending and taking first one, then the other of my balls in her mouth. She sucked until it was almost painful, then released me.

Usually, She would stop at that point and work her way back up, but this time she didn't. She went down to the skin below my balls, flicking her tongue and exciting me in ways which I had never before experienced. If anything, my erection became even harder, as that neglected area suddenly became a source of delight.

Clearly, as I was lying on the bed, she could not go any further, so worked her way back across my balls, up my shaft to the engorged head, which she finally took into her mouth and circled with her tongue.

I feared I might shoot my load there and then, ruining the evening, but she soon deserted my twitching member and proceeded back up my chest.

'On your knees,' she commanded as she reached my ear, 'now!'

This dominant Claire was so different from her usual persona, but I was loving it. One of the issues I found most tricky was having to take decisions about sex. I didn't really mind, but there was definitely something to be said for having that pressure removed and just going with the flow. I hoped it wouldn't be permanent, and would lead, perhaps, to a balance between our roles. For now I just wanted to enjoy it.

Once on my knees, and after some manipulating to get me just right, Claire lay on her back beneath me and pulled my cock into her mouth again. Her hands reached up and stroked my buttocks, gradually moving in towards the crack in the middle.

With one hand, she pulled my cheeks slightly apart, and I felt a finger from the other slide between, reaching my anus. She withdrew her head from my rigid shaft to allow her hands more room to work, and gently, with small, circular motions, worked at my sphincter.

The sensations were intense, and I began to understand how the writer of the website claimed to have had orgasms simply by playing with this small ring.