First time bi encounter : What was the biggest surprise or disappointment?

Derringer

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For me the surprise was it happened at all and my subsequent submission/ submissiveness.
My girlfriend ( of the time) had urged me to agree to expand our sex life to include other couples or mfm scenarios.
This came about after she had cheated on me with another guy ( purely for sexual gratification) . We didnt wish to break up over it as our overall non sexual relationship was very good. However she had been disatisfied sexually. She confessed that although the foreplay was generally ok she never got off when I actually fucked her. All of her previous boyfriends/ lovers were much better endowed and although she never considered herself a size queen my penis was paticularily small and did not stimulate her. I also had unreliable stamina and often came in less than half a minute. She told me she didnt mind that because if I pumped away any longer it only prolonged her pretending she was enjoying it.
Anyway I conceded to her wishes ( admittedly because I fancied the other woman who would be involved) They were known to my gf and she knew were bi and liked to swing.
I had not expected to engage directly with the other guy and in the course of the meet and greet they were fine with that. A date was arranged and initially interaction between he and I was periferal. However as things heated up both the women expressed a desire to see us get it on. They had already engaged with each other and decided we should do the same.
In the heat of the action I conceded to their cajoling (I had entertained fantasies about exploring same sex activity but never was attracted enough to indulge them in reality)
The next surprise was the main role I would play in this new experience. He was far bigger than me and both the women insisted I had to be the bottom. I wasnt actually kean on being the top or bottom and had thought it would be more along tge lines of fondling each others dicks or him sucking mine.
I pointed out that I was a virgin ass and accommodating him would be possibly a bit painful and problematic. Someone produced some lube and I was trepidaciously co-operative. I lay on my back and arranged my bottom for penetration. It did hurt somewhat when he eased inside but my discomfort was overridden by a brand new pleasure.
I was totally getting off on the feeling aided and abetted by the rush I got from the two women voying my submission to the 'superior' male. His huge manhood totally dwarfed my tiny dick as he pumped and mine jiggled about. I swear I almost came from this action alone but his gf grabbed my dicklet with a couple of fingers and a thumb declaring how she never seen her guy as so manly. I came volumously almost immediately.
That was the beginning of a long history of broadened sexual activity .
 
If I had a girlfriend that made comments like that to me, I'd dump her in a heartbeat.
I have been cheated on before. Similar reasons but I always broke up with them or they dumped me before confessing their indiscretions.
It was my first reaction to do likewise but she talked me around because otherwise we had a great relationship. The intrigue of an expanded sexlife which would include othe women as well was enticing and I dont regret indulging.
 
I been surprised by my submissivness in subsequent encounters but for the first time one my biggest surprise was the taste and feel of a dick in my mouth, i cant forget it. Not what i expected atall and so smooth n pleasureable. Guess i was hooked from my first dick
 
My first bi experience happened when I was lot younger, so very naive here. I had no idea, I could cum handsfree when my neighbour was fucking me from behind.

He used to give me "massages" previously that eventually progressed and led to anal probing with his fingers, which I enjoyed. Little did I realize that he was actually preparing my hole to take his penis all the way in.

That first time he did, instead of finishing off with hand relief, he moved and lifted my body to the edge of the massage table, mind you I was little petite thing and he was much bigger and stronger than me, so it was very easy for him to do.

I looked at him and asked, sheepishly asked what are you doing and he told me to just relax. Not that I had a choice or not, but I was curious and keen to know what he wanted to do. He spread my legs apart and had my legs raised and feet dangling over his broad shoulders. He then slowly and carefully inserted his lubed dick inside me.

As he started fucking me slowly and with a rhythm, I started to get more and more hornier. He made me moan and groan like a bitch. After a few minutes, the fucking got quicker and faster and so did his very aggressive animalisitc grunts as his body was spasming against mine. It was way too overwhelming for me and I blew loads of rope of cum all over him and myself and he nor I never touched my dick at any stage during the massage. What made it even hotter for me, he didnt stop nor care that I was done, seeing that I cummed everywhere seemed to have fuelled his excitement to the point where about 30 seconds later he blew inside me.

At the time, I was literally no pun intended blown away, that you could cum handsfree without your dick ever being touched.
 
my first bi experience was sucking a guy about my size in a public park. it was incredibly hot but he was really disappointed to realise id made myself cum whilst sucking him and so he couldnt return the favor...
 
Probably another surpise for me was how comfortable I felt in engaging in MM sex and the frequency when I was younger.

After my older neighbour went through the process of preparing me for anal and finally breeding me, I was surprised at myself how I sexually felt afterwards.

I would end up going to my neighbour's place almost every afternoon, either for a quick fuck or longer stay depending on the day and situation. Our quick fucks lasted less than 5mins and I would be on my way home. It actually got to the stage where both of us wouldnt masturbate given the frequency of our hookups. It felt unnecessary given how frequently we would have sex.

Looking back, I must admit it was a massive turn on sensually to be desired in this manner and it felt dirty and slutty on my part. Which I liked. The taboo nature of our sex was really a surprising stimulus for both of us.
 
I had been with girl but my first guy was kinda forbidden but as we went through the motion feeling his hard body on me the smell of his neck as we caressed each others bodies the feel of touching cock and balls other than my own we frotted each other until we came with him on top I lifted my legs and offered him my body he slowly pushed in with pain then feeling of good with him inside me
I really liked it more than tHan I thought I would
 
My first bi encounter was tonight. I went to an adult store with a friend that encouraged me to try the glory hole between booths. I’m a cocksucker now! The biggest surprise was that I got an erection as soon as I put his cock in my mouth. The disappointment was he stepped back and left before he fed me a load of cum.
 
my first bi experience was sucking a guy about my size in a public park. it was incredibly hot but he was really disappointed to realise id made myself cum whilst sucking him and so he couldnt return the favor...
It's not unusual for a guy to shoot his load hands free when sucking another cock. I guess you were really sexed up about the whole experience, frankly if I knew you'd cum when sucking me I'd have been pleased.
It's often the first thing a bi guy does - suck cock, and then go on to try other things. I had a neighbor one time who knew I was gay but kept on asking what it was like until, one night I told him to try - and that got me off knowing it was his first cock in the mouth.
 
Biggest surprise: how hard my dick got from sucking a cock

biggest disappointment: (I didn’t find this out until much later) I don’t really like getting fucked with big cocks.
 
That I would cum in like 2 mins! I had put so much planning into my meetup (my car), that when it came time to take my dick out for him I was already dripping precum. I felt his cock for about a min and I started to cum. Felt like a young man on his first drive in date! :p
 
I’ve only ever engaged in size comparisons, mutual masturbation and occasionally getting my cock sucked but the surprise has always been how much bigger the other guy has been. Even an inch can make a significant difference, especially if they are also thicker
 
Not being able to get hard enough to reach full mast. I usually watch straight-focused porn and most of my partners were women, and the thought of a guy sucking my cock never really occurred to me outside of my then curiosity. I had trouble getting hard as a result and didn't even finish.
 
If I had a girlfriend that made comments like that to me, I'd dump her in a heartbeat.
She was expressing herself honestly. What's so appealing about hearing lies? She didn't seem like she was nasty about it all, so her forthcoming should be applauded.
 
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Mine was a MMF and the biggest surprise was I liked sex with him. I did it as a “gift”of sorts to my gal, but once we were taking turns fucking one another…..damn. Had no clue it would be that good.
I wonder if he would ever let you take pics or videos... I'd love to check them out.