For helpful but by no means requisite context, our story began with [this very memorable evening of firsts](https://www.reddit.com/r/gonewildstories/comments/ihgl4v/my_opening_a_whole_world_of_exploration_in_my/) – a night spent with an older bisexual couple who patiently introduced [m]y – at the time – college aged curiosity to a world of sensuality, exploration, and kink.
After that first incredible evening, my sensual world had opened up and, perhaps needless to say, we all stayed in touch even as their trip into the city had ended the day after we met up. In the interim, we spoke over e-mail with plenty of photographs exchanged, fun debriefed, and an occasional sexy call or text from Anne, the wife.
To my horny relief, before long they were making plans for their next trip down to the city.
So it was, probably two or so months after our first night together, I was once again walking into the lobby of their hotel, butterflies in my stomach, and a sneaky and cheesy grin probably plastered on my face.
I wore jeans and a nice blue button down shirt. I often think that because the visuals are so much more fun, women and their outfits get all of the attention but as a guy, there’s subtle decisions that can be sexy in a partner and, perhaps as importantly, as the individual making them. What’s sexier than *feeling* sexy?
For me this evening, those decisions were indeed subtle – I had skipped my usual undershirt knowing that my shirt wouldn’t stay on for long and I had gone with my tightest pair of boxer briefs – the ones that supported, cupped, and made me feel sexy in the way I imagine women must feel with a great piece of lingerie on. Add on my freshly shaving that afternoon and – as silly as it might sound – I felt downright sexual as I texted them that I had arrived downstairs.
This time they would both join for a drink – they let me know they were in the bar upstairs – it was empty and more private. As I joined them for a cocktail, we hugged hello and flowed easily into conversation that had, digitally at least, been on-going for the past two months since we first met. As we hugged, Anne’s perfume was instantly familiar but my first experience so close to her last time was already quite intimate and those sense memories flooded back to me, tightening my jeans as we sat back down for the drink. Perhaps recognizing that added excitement, Anne moved her chair closer to me so our knees were touching as we caught up.
Not long into the conversation, James mentioned that a while back they had a very fun evening with a very sexy woman closer to my age who was dominant. He said they had invited this Domme to join us that evening. They had also invited another younger bi guy who they thought I would get along well with but it didn’t look like he was going to be able to join. With a smirk, he offered up that if I wasn’t comfortable with the Domme joining, they could call her off but they figured I wouldn’t mind. Trying to play cool my excitement but also nerves, I smiled and probably muttered a “yeah, sure” sort of response. Leaning back in his chair and satisfied they had assumed correctly, James said she was going to join for drinks in a few and then if we all got along, we could all go back up to the room together.
As my heart beat out of my chest in anticipation, our conversation continued but thinned out as the direction of the evening became clear and we all were, on some level, waiting for her to arrive. Breaking this tension, the cocktail waitress returned to top us up on drinks. As the waitress took James’ order, Anne leaned in to me, whispering in my ear with as much a question as a statement, “she’s bringing her strap-on and I’m excited to see her fuck you.” She leaned back, watching my reaction and nearly giggling in glee and imagination at my nervous, excited, and impatient reaction.
With that, Erica arrived and just when things seemed at their anticipatory height, here was a sight for sore eyes. Erica was indeed closer to my age though still slightly older – probably around 26 years old – tall at probably around 5’9″ or so (to my 6′), and a gorgeous, athletic woman of Thai descent – long dark hair, tanned skin, and a smile that would make any man trip over themselves to serve.
As I stood up to greet her, Anne and James introduced us. First by name and then, just as I was exchanging a firm handshake with her, Anne added in – “he’s the sexy boy we told you about who we met last time we were in the city.” With that, Erica smiled, might have just been my embarrassment but it seemed Erica’s handshake almost tightened at the connection and her enjoyment at my now deep blush. It felt in that moment as though Erica might as well have been there to see the final moments of our last meeting – as I lay naked, head between Anne’s legs, face covered in her juices as James pulled out of what had been my first time getting fucked.
With that, we all sat down and chatted for a bit. Turned out that Erica was in medical school – splitting her time between a medical research job to put herself through school. Beautiful, sexy, dominant, *and* probably smarter than the rest of us. We talked about the good and the bad of that job for a while – James was in medicine too – as well as my career and recent work especially as Anne and I were in a similar industry that everyone (but me) loves to talk and hear about.
***********Fun Begins Here*******************
Before long, Erica seemed to grow impatient as she looked at the three of us and finally asked to no one in particular, “shall we?”
All three of us nodded but just as we started to look to pay the tab, Anne grew a smirk and locked eyes with me. “Jay, let us get this, you’ll make it up to us, I’m sure. How about you go up and turn the lights down in the room so it’s ready for us? I’ll give you my key.”
“Happy to!”
As I stood to go, Anne stood up to hand me the room key. As I reached out to take it from her, she pulled me in to her so she could whisper in my ear.
“Leave the door ajar and only the reading light by the window on. Once you’ve done that, I want you to strip down to your underwear and lay face down on the bed waiting for us. You understand sweetie? Hurry up there as we’ll be close behind you and I better not find you still clothed when we come in.”
As I walked away, Erica called back towards me – as I turned around, she stared deeply into my eyes as she knowingly said “See you soon, Jay.”
Nearly jogging down the hallways to the elevator and then waiting on what seemed to be the longest elevator ride of my life, I finally got into their room. Not wanting to forget the key step, I put the door bar in the door to keep it open and set about turning lights off as Anne had asked. I then looked around the room – as silly as it sounds, Anne’s charging me with getting the room ready gave me a sense of both pride to do the job right and nervousness as to the consequences – however vague they might be. With a quick moving to the side of a pair of shoes and a folding of a towel, I quickly stripped down – too nervous and hurried to feel sexy or savor it, pressing instead towards the moment I could get onto the bed and wait.
And so there I finally was, lying face down on the bed, naked but for my tight boxer briefs, a mix of nerves, hormones, and excitement. Only in lying down on the bed and finally waiting did I realize how hard I had been, the firmness apparent when pressed between my stomach and the mattress – pressing at the waistband of my boxers. Then the wait began, it seems long but was probably merely a few minutes before I hear them coming down the hall, laughing as though their conversation had only heated up with the anticipation inherent in the walk from the bar down to the room. The conversation softened as I heard them open the door – perhaps not wanting to draw attention to three adults clearly unrelated to each other entering the same room. Once inside, I waited, now with my sight darkened as I put my face straight down into the sheets – wanting to be obedient and thorough.
With that darkness came a heightened awareness of everything else – the push of air from the hallway onto my naked legs as they door opened, each breath and step of the three of them entering the room, and finally, their reactions.
First was Anne’s – “Well, James, you’re not going to let him be there all by himself, are you? Get naked and lay down next to him. Now.”
As I hear James starting to undress, more footsteps and the feeling of presence near me.
Now Anne’s voice seemingly right behind me, “I told you he had a cute butt, didn’t I?”
No response from Erica but the sound of someone stepping closer to me and then, with a jolt of surprise from me (and probably a visible but small jump), Erica’s fingers curling around my boxer briefs – finger right at the top of my butt crack – and pulling them down below my butt – held up below me by my now straightened hard-on caught in the waistband but nonetheless leaving my butt exposed to what I could only imagine was Anne and Erica’s appraisal.
Finally, Erica, “Very.” With that, her other hand came slamming down on my right cheek in a surprising, solid, and oddly satisfying spank.
“Stand up, Jay” Erica said.
Leaping up, I stood before her, out of a perceived (probably porn-informed) sense of protocol but also some level of propriety, I stared at the floor as I faced her, boner pulled at the front of my briefs but my butt still bared in the back. There I stood, as, from their feet, I saw Anne and Erica looking me over.
“Take them off.” As I bent down to take my boxer briefs all the way off, I felt a hand on my back and a presence at my side, looking over, it was Anne who guided me around so that I stayed bent over but now with my chest on the bed. By this point, James was naked on the bed – having be instructed to join me. I realized Anne had guided me so that I was bent over right next to his hips. Looking over as he casually and gently was touching his semi-hard cock, it became clear what would come next.
Anne again – “get to work while I undress. Then it’s my turn with you first.”
Eager to end the waiting and examination and get to the work I by now had learned I absolutely loved – pleasing – I stepped over – still bent over the bed – and kissed my way up James’ legs – using my hands to follow and pet his thighs until my mouth reached center and I took his cock head into my eager mouth. Now nearly hard, I swirled my tongue around the head before starting to warm up with slow, tentative bobbing. As I started to focus in on my still very nascent cock-sucking skills, I was reminded there were others in the room as Erica’s hands stroked up and down the back of my thighs – grabbing and teasing before the occasional – though increasingly frequent thudding spanks that would send James’ cock deeper into my mouth as I was pushed forward.
Just as this became to feel like a rhythm, the bed moved with Anne’s joining us. She grabbed underneath my shoulders and sort of pulled me up to be leaning on top of her as she said “like I said, he’s mine first.” With that, she kissed me deeply and then flipped me over – grinding our naked bodies together as I grabbed and stroked as best as I could keep up – over her back and butt and ample breasts. As I leaned down to try and suck on her nipples, she scolded me – “I have other plans for that mouth.” As she pushed my shoulders down into the bed, she crawled forward, lowering her pussy onto my waiting mouth and tongue.
Where our first time together she was sensual and gentle even in her moments of control, tonight there was a carnal passion and need I was unfamiliar with. Neither with her nor any partners my age had I yet felt the full power and confidence of a woman getting herself off on me – in this case with my tongue and face – and I was instantly in love. Drunk on the passion and juices now covering my face, I did my best to lap away as the rest of the world fell away in my focus to do right by her. Once I felt I had some rhythm, I reached my hands around her thighs to grab her butt so I could pull her even tighter and closer – simultaneously pulling her in and hanging on for dear life until I started to feel the tell tale vibrations and building in her legs as they shook around my ears into a powerful first orgasm of the night. As she climbed off of me, she looked at Erica, smiling and motioned her over.
Still catching my breath, I put my arm out – in what seemed like a common and sensual gesture of wanting to pull Erica in to me. She accepted this entree and leaned in to kiss me but not before liking Anne’s juices off of my cheek for a taste. Kissing me forcefully and deeply in a way I hadn’t ever experienced, she climbed on top of me as my hands explored her back and a tight butt and legs I can still “feel” to this day even as she never took her bra or panties off. Caught up in those sensations and exploration, I at first missed what became most clear when she started to grid her body against mine from on top of me – she had an unwaveringly hard rubber dildo in a strap-on harness that was now grinding against my crotch. I noticed just in time to understand the question that came quickly thereafter, “are you ready?” Full of nerves, I nodded and she climbed off of me then grabbing my ankles – first pulling me to the edge of the bed and then putting my heels against my butt on the edge of the bed so that I was wide open for her.
She called James over to distract and please me with his mouth as she pulled from her bag a condom and a seemingly Costco sized bottle of lube. James lowered his mouth onto my cock as she started to cover my butt in lube before gently but urgently starting to finger me. Too excited and far too sensitive for my own good, I just about shoved James off lest I explode right them. He looked confused before seeing the hungry look in my eyes and understanding it all. And with that, she slid into me – smoothly, softly, and yet still with a firmness that made abundantly clear who was fucking whom. As she reached and stretched my ankles to rest on her shoulders, she started a rthymic fucking, grinding at the bottom of each motion for her sake. Unfamiliar with this distance and sensation – being fucked but laying on the bed as a woman I barely knows stands to thrust into me, I craved intimacy – I tried to sit up – stopped by my legs. She put my legs back down and prompted me to wrap them around her hips – I loved the intimacy and the enthusiasm it seemed to indicate as my feet now pulled her in with each thrust. Now freer to move, I sat up to kiss her and grope her incredible body – the body that was now fucking me with an increasing force and passion and speed. She humored some making out (a favorite of mine in any circumstance) but would then push me back down and speed up. Eventually, sensing my need to have more than just sitting there taking it, she told James I needed something for my mouth to do.
Needing no more prompt than that, James kneeled next to me and cradled my head in his hands so that I could take his cock in.
So this continued – probably for longer than anyone has ever been inside me since. A magical, blissful sort of sub space of pleasing James and being her fuck toy with the occasional petting of Anne alongside me. At one point in that blur, Anne used her strap on with James before them swapping so he could cum inside her. As she climbed on top of me, cum dripping out of her pussy, she rode my face once more to an even wetter orgasm – at which point – somewhere during Anne’s orgasm, Erica pulled out of me. As Anne climbed off of me, Erica leaned down to whisper in my ear that I had done a great job – filling me with a perverse but deep pride even before she then wrapped her still lubed up hand around my cock and jacked me to an admittedly *very* quick orgasm – turning my cock up towards my face to make sure that my, by now quite substantial load ended up all over my chest and even chin.
With that, she sat back in a chair in the corner of the room to watch. Sometime around this time, James took a break to check his phone and saw that their other bi friend – who they had mentioned earlier – had freed up and was nearby and could he come up. Everyone agreed though Erica said she’d be heading out soon as she had to work the next morning at 6a.
With a new guest on the way, Anne invited me to help her wake James up.
We started to suck James together – tasting his earlier orgasm and Anne on his cock as we made out with him between us. Eventually, their other bi friend arrived and Erica ended her night watching as James, the friend, and I formed a sort of blowjob triangle prior to James’ getting behind him. But I’ve already written too much.
Until next time – hope you enjoyed – love to hear comments whether on here or message!
Source: reddit.com/r/gonewildstories/comments/j28jst/second_time_with_my_first_couple_bi_mf_leads_to
this sounds like such a perfect night
Sounds like a great time!