First Bi-Guy Experience

If you think you might enjoy this real life effort from me could I suggest that you read my first two real life submissions? In my first Literotica effort I wrote about an affair with an older woman, Muriel. From day one I have had a thing for older women, my first being when I was 17 with a firecracker hot 46 year old neighbor that I had known since I was eight. I was 34 when I met Muriel who was 56 when we first went out for lunch.

I am an older guy now so this real life experience was many years ago but like some of my other experiences in my thirties it remains indelibly etched in my mind. The first few paragraphs might seem a little vanilla and removed from Bi but they are a stark contrast to where this amazing woman took her and our sexuality.

I knew Muriel from our tennis club where we would chat after our games. I had never played tennis with her, but knew that she had limited ability, whereas I was a ranked player in Ontario. I took some time to give her a few lessons that seemed to help her game. After one of these lessons she offered to take me to lunch as a thank you. Over lunch it was clear from the flirting and teasing that there was a mutual attraction.

For me, she fit my kink for an older woman; she was attractive and in great shape; and I found an appeal in that she was refined, a nationally known figure in Canada, and had even addressed the UN. She accepted my invite back to my place for a glass of wine. I think at that point we both knew that a decision had been made.

I am not usually very direct, but when she took her glass of wine out to the balcony for the view I followed her a moment later and started to kiss the back of her neck. She responded with a little shudder and slightly pushed back against me with her backside. While I continued kissing her from behind I reached around and began to fondle her amazing breasts, and moved from fondling to unbuttoning her blouse and releasing the front clasp on her bra to release her surprisingly firm breasts.

So here I was partially undressing her in semi-public on the balcony, massaging her ultra-sensitive nipples and we had not even kissed yet. I found this to be a real turn on and when she started to turn around I held her in place. I was enjoying this control and exposing her on the balcony while I brushed away her halfhearted attempts to cover herself. She later admitted that she was getting off on this.

Finally I turned her around and was thrilled to find that she was a passionate deep kisser. Moving to the bedroom I undressed her and took my time exploring her with my tongue and hands. As I began to finger her moist pussy while we were passionately kissing she had a mild orgasm, if there is such a thing. She gave no sign of needing a break, so I decide to kiss my way down to her pussy. Before my tongue was anywhere near her clit she was letting out low moans and writhing.

I decided a tormenting build-up was in order and spent some time kissing, licking and nibbling her upper thighs, buttocks and pubic area...taking care to avoid the sweet spot but maintaining a prolonged tease that was getting lots of reaction. She jumped as if she had received an electric shock when I started to rim the outside of her anus, and really got into a rocking rhythm when I stopped flicking my tongue and started to drive it into her lovely pink anus.

When I looked up I saw that she had pulled a pillow over her face and was softly moaning into it. When I slid my tongue from its ministrations to her anus and into her vagina she threw of the pillow and put her hands on the back of my head and created her own rhythm with my tongue by pulling me into her. At this point she was really moaning and into it. I was in no hurry to bring her to orgasm. This was our first time in bed and I had her completely at my mercy and I was really enjoying the way that she was enjoying being pleasured.

Finally I moved the tip of my tongue to her clit and began to barely lick it, just teasingly flicking it, hardly applying any pressure. Frankly I wanted to really draw this out to the point that she would just about beg to cum. To my surprise, she came quite almost instantly and violently. Surprisingly, she then began sobbing a few tears. When I took her in my arms she explained that she had only had sex with one man before me, her ex-husband of 35 years. He was not only a dud in bed, but something of an all-round pig. She had never had a man go down on her and had only tried giving a blow job a couple of times. All of this of course was related to a dull sex life with her dullard ex-husband.

We chatted while kissing and cuddling. She told me that this oral experience was the most exciting sexual experience ever for her. She had spent her life imagining what it would be like so this first time was a massive release. From there we saw each other frequently and really tuned into each other sexually as her long suppressed desires were awakened. I was hugely turned on by her genuine openness to share her fantasies, including bondage and spanking.

We both loved it when I would tie her hands behind her back and have her kneel down and suck on my cock, and then I would alternate this by pulling her up over my knee and giving her a pretty hard red bottomed backside spanking. We had a safe word that she never used even though I sometimes brought a tear to her eye. One night she coyly shared a fantasy to have a MFM threesome. Over a couple of weeks she brought it up again and it was clear that she was turned on and actually interested. I suggested that we meet my friend James who was very much into 3somes (and was Bi) for coffee to see if there was a mutual attraction, and sure enough they hit it off and a date was arranged.

It would be an understatement to say that our first 3some together was fun. It was erotic, raunchy and there were lots of laughs and good conversation. I really got off sitting back while I watched her being fucked by my good friend James, and she would playfully look over to me and smile from time to time. James had lots of ideas and had the wild idea to have Muriel kneel on the floor and perform oral on both of us. She later told me that having a cock in each hand and alternating them into her eager mouth was a real turn on. It was astonishing to watch and chat about her performance while her hands and mouth were full! She certainly had a few hours of undivided attention that afternoon as we tried almost everything imaginable in a threesome.

Her favourite was lying on her back while one of us performed DATY on her while she was DFKing with the other. She was not shy about telling us to switch positions from time! It was also a huge turn on for her and me to have her lay between us and move her head from side to DFKing James and then me. I just loved watching from so close as she and James wrapped their tongues together as they kissed. Almost like team work we moved from her mouth to her ears to her nipples which she really liked. They were very sensitive, especially the tips. She confided that on top of feeling great, including an involuntary mild orgasm, that having both nipples being sucked at the same time was an enormous ego boost.

Our meetings with James were somewhat regular and always hot as hell. I had always fantasised since puberty about trying Bi. It was more than a passing fancy as I thought about it often and had some great fantasies about it when I masturbated or even when I was having sex with a woman. It never crossed my mind that it could become real which was a shame because as I watched my friend James fucking my BFF cougar friend Muriel, and watching her sucking his rigid cock I was actually a little jealous and of course turned on in more ways than one.

One day when Muriel and I were alone in bed she mentioned that she could see that I was really turned on watching her. She mischievously confessed that when she was performing oral on James she made sure that she positioned herself so that I could get the best view possible, often winking at me as she slid his cock slowly all the way in and out of her mouth, knowing that this was something that I really liked. She said she felt like she was performing in a porno show for me. Now she certainly had this right but little did she know that there was a little more to it than I could admit.

If you have read my first Literotica submission you know that my first Bi experience with James was a sort of fluke and just the two of us. This left me in a quandary. Muriel did not know about this and I felt that we could hardly get together as a threesome and have this as a secret. Apart from anything else how would I be able to resist his cock? I was pretty sure that Muriel would be turned off by this. I had known a few women that professed to be really turned off by man on man sex. We were good friends and I owed her the truth so I arranged to meet her for lunch fully expecting her to be turned off and end our arrangement. To no real surprise she was certainly taken aback, explaining that she thought I was the last man on earth she would have expected to try Bi let alone going as far as the bottom in anal.

The surprise was that she thought it was erotic. She had known that James was Bi and had wondered if he would ever approach me. In fact she thought that he might well ask me, be rebuffed, and that it could end our 3somes. I could tell that she was genuine about this as she wanted to know all about it in as much detail as I could provide. We went back to my place in a state of high excitement. I had told James that I would be telling Muriel and my concern that she might end the relationship. So before we climbed into bed I called James, put him on speaker phone, and we had a fun 3 way chat with some inferences from James and Muriel about how I was to perform for them.

When we got together a few days later I was surprised to see a side of Muriel that I had never anticipated. This was the take charge Muriel. In our relationship I had always been the take charge and take the lead partner. She later explained that she really enjoyed this but now knowing that I was the sub in Bi that this had given her some new thoughts that excited her. With this new dynamic there was a little nervous awkwardness when we all sat down with a drink. Seems odd given how intimate we had already been with each other. I usually started things by slowly caressing Muriel but as soon as I started she gently stopped me and told James to strip down and come and sit next to her. She then told me, fully clothed, to kneel in front of James.

She than took his flaccid cock and pushed my face down and told me to make it hard. So there I was performing a blow job with an audience for the first time. I have to say I found it a turn on doing this while they casually chatted away about my performance and Muriel playfully telling James she never thought she would end up dating a cocksucker! Listening to her instructions while I was down there was not only exciting but playing into this new found submissive persona that I was really getting into. Instructions like "lick his shaft"; "suck his balls"; "deep throat him". The best was to tell me not to use my hands as she wanted James to cum someplace other than my mouth. James was hugely into this as he was as erect as a flagpole without too much oral attention from me. After a while she told us to stand up and asked James to undress me.

This was an odd feeling being undressed by another man, but I could tell that she was enjoying this and giving instructions. Her next instruction was for James to kneel down while I was standing and suck on me. This was a first for me with James and I was really enjoying it. As much as James was the Bi take charge guy he really enjoyed performing oral. While he was blowing me I asked Muriel if she was OK with this Bi thing and she excitedly exclaimed "are you kidding, this is fun".

After a while she suggested we go up to the bedroom. She asked James and me to get on the bed and perform a 69 for her. She explained to me much later that night that she had never seen a blow job being performed, even in a porno, and was surprised how much she enjoyed watching. I know that James and I, knowing that we had an audience, were trying to make it erotic looking in addition to giving our partner satisfaction.

As she was watching, Muriel finally undressed and sat on the edge of the bed. I was on the top of the 69 and as my cock was sliding in and out of James mouth she fondled my balls, which was electrifying under the circumstances. She then moved to the other end and lifted my head by my hair and slightly pulled my mouth off of James cock, took his cock in her other hand and then used me by alternately pushing me down onto to his cock and then pulling me up, essentially face fucking me with James erection. Occasionally she lifted my face up by a couple of feet so we could kiss and then before she had me resume she would take a minute to suck on James herself.

At one point when we were kissing she whispered in my ear "I cannot believe that you were worried that I would not enjoy this". After a while she asked us to switch 69 positions and she kept up her attentions, only reversed. We had been at this 69 for some time when James stopped, lay on his back and directed us both to go down on him. It was strangely exciting to team up, put two mouths on his erection, watch while one of us deep throated him and then passed his cock to the other to carry on. We managed to contort ourselves at one point so that I had his balls in my mouth while Muriel was sucking on him.

The newly assertive Muriel decided that it was time for a change when she announced that she wanted to see me fucked by James. She explained, "after all, he has fucked me enough times!" She asked James how we were going to go about this. At this point it took me some time and preparation to get loose for anal and I had only done it lying on my stomach, hips propped up on pillows. As I settled myself in the position James took out the KY but Muriel took it from him and said she would like to do it. She had never finger fucked me in our one on one sessions. She took her time and as my sphincter loosened she inserted two and then three fingers. Having gotten me loose she then started to really finger fuck me to the point that I was bouncing up and down to her rhythm and driving my ass up to her hand as I anticipated her next thrust.

I had my head buried in the sheets focusing on and enjoying the moment as if it was my last day on earth. I was intent on not losing this great rhythm that I had going with Muriel's driving finger fucking. When I did turn me head sideways I saw that while she was finger fucking me James was kneeling on the bed with Muriel sucking on his cock. To different degrees and for our different pleasures all three of us were moaning a little at our various enjoyments.

Without changing position Muriel had me prop myself up on my elbows and told James to kneel in front of my face so he could take my head in his hands and pull me down onto his very erect cock while she kept her fingers inside me albeit no longer finger fucking me so rigoursly. She then announced that she had me ready and that it was time for, as she described it, the main event. She seemed to enjoy taking his erection and guiding it into my anus. James knew that I liked the sensation of him slowly sliding almost all the way out and then slowly back in again.

As he did this Muriel stroked my back and from time to time leaned over and kissed James. He was certainly in heaven. After a while she positioned herself so that with a small adjustment in position by me I could lick her clit. It was an awesome scene. James fucking me; Muriel having her pussy licked; and the two of them happily chatting away while I was busy being used on both ends. James finally came quit violently to some pretty hard ass fucking on me. The rest of the afternoon passed with Muriel pretty well being the centre of attention, and finally James left. As we cuddled in bed Muriel shared that she had really enjoyed this new level of our sex life.

It was 4 weeks before our schedules allowed us to get together again, but in the meanwhile I had seen James a number of times. More and more he became sexually dominant and I had become his sub. He had seduced me into moving on from my preference to be fucked while I was on my stomach. I had gone from real awkwardness about the missionary position to wanting, and some days, needing to be fucked like this. I would wrap my legs around his body and do everything I could to find his rhythm and contract my anus to squeeze on his cock. There was no question that he had his best orgasms when he was taking me this way as opposed to me lying on my tummy. He told me it was a big turn on when I explained that it was not only very sub to be taken this way but also felt very feminizing for me.

More and more James was discovering my attraction to the pain side of being his sub. He knew about this from biting my ass as he went through our ritual of getting my ass ready for him slide into. He had progressed me to being bitten all over. We had a code of "8" is very hard and incredible, "9" is just about too hard and "10" too much. Codes that I still use today in my BDSM world. There is something electrifying in BDSM about losing all thought and control when you are driven to focus in a tiny moment controlled by pain and at the discretion and control of someone else. When James had me ride him cowboy style for the first time he added a twist that took me by surprise.

While I was riding him he held both of my nipples and squeezed them hard to the point me almost not being able to bear it. Not only that but he also pulled up and down on them to the rhythm of his thrusting his cock up inside me. And this time not to my normal slow in and out. I felt like a rag doll bouncing on top of him and was moaning from being driven so hard and from the pain being inflicted on my nipples. In truth if this nipple pinching and pulling had not been during intercourse I would have cried stop. But I could see that James was perhaps more excited than I had ever seen him before. When he came it was with a real rush and whist I was really happy to have satisfied him like this I knew that I could not have continued much longer.

James owned a dental lab and was quite well known for building models of trains, planes and boats. So he was quite a craftsman. Knowing this, I did not expect his next surprise. He built a leather harness that went around my waist and upper legs. It had two brass handles that he could hold and it also had two restraining straps that could bind wrists. By this time in our relationship I was past reservations and looked forward to the thrill of my sub role. Inwardly I was not too sure about this harness, but put on a brave face to try it out for him.

After some initial foreplay James had me trussed up in the harness, bent over doggy style, with my wrists secured behind my back by the restraining straps. It felt completely vulnerable; exciting and nervous beyond words. It was my first time being used in doggy. James left me in this position for about 30 minutes without attempting to fuck me. During this time he spread KY on my balls and cock, and took my balls in his left hand and fondled my cock with his right.

He had no intention of allowing me to cum but had me in a continual state of high arousal. He varied this with erotic biting on my back, sides and ass. He had mastered the pain art of keeping me at my pain level "8" so between this and his KY ministering it was 30 minutes of bliss. When he finally positioned himself behind me he began by working his finger fucking magic to loosen my poor ass. Because of the position that I was in I had not been able to suck on his cock so he was not quite erect, certainly not enough to enter me. He soon fixed that by sliding his cock up and down between my buttocks. And then the moment for penetration arrived. I was not sure how I would be able to handle this in doggy, warmed up or not. It was a little more difficult than normal but James was a master of careful penetration and eased me into a state of penetrated relaxation.