First Time
Aug 19, 2019


Preface: This is a X-Post from my reddit account. I wanted to share this on my SwingersHeaven profile, because for interested parties, the details within help to illustrate the kind of partner I am. Still, if you're just interested in hearing a descriptive and thoughtful ex-virgin's perspective on his firsts, from first time holding hands with a woman all the way to first time being deepthroated by a man and fingerfucking a woman's g-spot at the same time, read on! You might jut enjoy it. ;)

Eleven things I liked and enjoyed:

First time I’ve held hands with a woman! I know!

First time I’ve been given permission to look and stare at a woman’s body.

First time I’ve been given permission to touch a woman’s legs, arms, run my hands across her back and shoulders, down her neck etc.

First time ever seeing a woman in lingerie up close.

First time I’ve ever taken off said lingerie.

First handjob I’ve ever received, both from a man, woman, and both simultaneously.

First time I’ve ever hotdogged a woman’s ass.

First time penetrating a woman. Just the tip, this time. Thrusting was very fun to do!

First time grinding & teasing a pussy with my cock.

First time I’ve had my prostate stimulated, no penetration. So, right on my gooch...uh, my perineum. Not gooch. :P

First time anyone has watched me take a piss...and enjoyed watching? If he liked it, then I suppose I liked doing it for him! Certainly wasn’t uncomfortable or awkward, which I was surprised to discover. M and K just made me feel so so so comfortable.

Six things I was extremely into and want to do or try again:

First time I’ve ever fondled breasts, suckled on nipples. It's even better than I had imagined, and I have a huge nipple fetish.

First time seeing, touching, fondling a vagina. Wow, these things and their many pieces are just asking for attention! I couldn't get my lips on or around it during our first night due to some unforeseen circumstances, but I eagerly await the day I can kiss and lick it with the same adoration & intensity I did with K's lips. Unfff.

First blowjob I’ve ever received, both from a man, woman, and both simultaneously. I really liked receiving a blowjob from both M and K, especially the hard head-sucking and frenulum-based tongue flicking. Hooooh boy.

First time seeing, stimulating a clit. I really want to practice this more, attune my fingers to being able to find it when when I can't see it or an not guided toward it by K.

First time having my foreskin, balls and shaft fondled & caressed. Felt great. M spent the most time on my member while I kissed and fingered K, but both had turns and both were thoughtful and delicate with my foreskin, which I really appreciated. I had hesitations about simply allowing them to explore me without trying to instruct, but they were so good to me, so kind and delicate. Those hesitations turned out to be completely unfounded, thanks to their care and attention.

First time smelling and tasting pussy juice! I’m a BIG FAN! Even the faint smell on her panties got me excited! Tasting it straight from the source in the future is going to be very enjoyable.

Ten things that were the most intense, arousing, enjoyable or emotionally resonative:

First time anyone has sincerely, in person, complimented my body. This one struck me right in the heart. Years of shame and insecurity tossed to the wind by a few simple, heartfelt words. I was already feeling very confident and independent after getting my first car about a month ago, but this realization here? This was like planting the flag at the top of Everest. This was punctuating all those sentences I had written in my head about body positivity, suddenly making those sentences complete.

First time sharing a person’s embrace in bed. The warm & appreciative aura of attraction and love is something I struggle to put into words...Aftercare, afterglow, post-sex snuggles, whatever you want to call it, it was heartwarming and so nice. Words fail me! It was just fucking nice to be held by someone and to hold someone. I really enjoyed it.

First time fingering a woman, finding her G-spot. None of my wildest imaginations or dreams could have prepared me for what a vagina feels like. So many layers and layers of soft, sopping wet flesh, exceedingly warm & slick. An utterly unique texture unseen anywhere else. No matter where my fingers went, they were greeted with her tightness enveloping me, begging me to venture further. And finding her G-Spot and carefully tapping, pressing and drawing circles upon it with firm pressure...it was a really great thing for me to feel. The warmth, the slick wetness, the many folds and waves, the way she tightened and sucked my fingers inside her...pussy is perfect man, it's perfect!

First time hearing a woman scream out in orgasmic ecstasy when touched, suckled, slapped, teased. First time I’ve seen and felt a woman’s orgasmic contractions/convulsions. With every mind-tangling moan she released, my heart would beat and my cock would tense up just a little harder. Feeling her cum on my fingers and tighten her grip so hard I'd have to work to pull myself out of her was awesome. Seeing her orgasm was also really beautiful and erotic. But hearing her voice, how raw, expressive, unfiltered, how honest her body was choosing to be when my touch sent her into an orgasmic repetition of convulsions...it was the sexiest, most attractive thing I’ve ever seen, and produced within me a hunger to satisfy her again and again. Watching K cum and knowing that it was me who caused it was the second-best part of the evening, and will probably be the best part of future visits. This is my #1 turn-on, watching a woman cum, and knowing that I'm the cause. Making K feel good makes me feel good, regardless if I'm cumming as well.

First kiss, first time making out, french kissing, tongue sucking. Kissing feels FANTASTIC, physically and emotionally. It’s incredible, and I desperately want to kiss a whole lot more. The sound of kissing and licking immediately gets me hard, and when we gave each other’s ears attention, all the pinching, kissing, biting, breathing, licking, tongue fluttering...Every time she touched my ears with her mouth, my cock stood at attention and dripped precum like a faucet. Kissing. Is. Amazing. The sounds, the smells, the tastes, the feeling...

First time I was able to explore the flavors and textures of a woman’s tongue, lips, nipples. Especially the nipples. Just thinking about them gently sliding between my tongue and teeth so I can feel all their engorged ridges & wrinkles makes me eager for more.

First time I was able to squeeze, kiss, lick and appreciate a thicc woman’s curves. Her back, her hips and their dimples, her stomach, her thighs and calves, her biceps, her mound just above her vagina, and of course her incredible ass...Thicc women feel utterly amazing, no matter where your fingers reach. I loved exploring her many curves, and excite myself every time I think about them.

First time I was deepthroated, both by a man and a woman. HOLY. FUCK. This was the second most intense feeling of the night, when either of my partners would shove my rock hard or semi-hard member deep down their throats...feeling the ridges and walls of the grooves of their mouths, feeling the detailed bumpy texture of their tongues glide across the base of my head (where I’m most sensitive), and feeling the top of my head plow across the back of their throats...these were my loudest and most expressive moans, during the deepthroating. Both partners had different techniques; Fast up & down motions, pushing deep & holding themselves against me, sucking in and blowing out air to shock my cock with quick temperature changes, frequent breaks in the thrusting to apply loving and careful attention with their tongues between my foreskin and my head...I enjoyed it all. Truly delightful.

First time a man has grinded against my shaft, balls, asshole, perineum, no penetration. I didn’t even anticipate how good something like this could feel, mostly because I am not attracted to any masculinity and never even thought about a guy grinding his junk on another guy's junk...but this really really felt great. Like, REALLY great. Like, you know in heavily produced porn (and sometimes amateur porn as well) when you see the eyes of a girl roll back in her head, her mouth's open but she's breathless and wordless, and her arms go limp when her partner's hitting the right spot? It felt like THAT. It’s what caused the pins & needles in my arms and legs, eventually leading to me needing to take a break, stifle a leg cramp, and get re-hydrated. It gave me a sensation I had only ever felt localized in one limb; NEVER across my entire body, shooting across my chest into my fingertips and toes like lightning. The numbing sensation it gave me was a little frightening at first, but I enjoyed it a lot, with tears peeking from the corners of my eyes, arms crossed on my chest and hands digging into my biceps, small moans escaping my mouth and turning into loud, guttural cries of ecstasy. This was really really great, but during the last 30 seconds, M put my legs onto his shoulders, which gave him even easier access to my hardware, but we suspect also resulted in my leg cramp. Was still worth it though.

And lastly, the first time I felt truly vulnerable and exposed, both physically and emotionally, and was given comfort, pleasure, patience and understanding. This was the only time in my life someone, anyone, has wiped a tear from my eye, kissed me sweetly, and told me that they liked me for me; My body, my looks, my personality, all just the way I am. Not trying to be overconfident, not pretending I'm a know-it-all, not sheepishly self-deprecating my abilities...just being me. This is when I began to break down into tears of joy, when I recognized how sweet & honest my partners were, and how they adored me for me. How they were dedicated to making my first sexual experience something wholesome, heartfelt, and truly memorable. These two cared for me, and it showed throughout. And for that, I simply cannot thank them enough. My emotions run high simply thinking about it….M & K, from the depths of my heart, I thank you for all that you did for me that night.

Three things I’d like to do next time that we didn’t get a chance to do:

Learning how to eat a woman out, where to suck & touch with my tongue. I’m aware it will vary from woman to woman, as we discussed thoroughly when I was exploring her body. I want to learn how to explore, how to find the spots that excite my partner and how to listen and feel the cues that her body reveals to me. If the scent of her pussy and the taste of her dripping wetness were anything to go by, I believe I will become very aroused & enamored with the act of eating women out.

Full penetration, and some specific positions. Because of some unforeseen circumstances, full penetration was not an option for our first night together. I anticipate experiencing the full length and the sucking, slippery warmth of her pussy. Every inch, every wall, every little fold and curve, I want to feel it all, from several different positions, and I want to learn which ones she likes the most, how we can change the feeling based on angle, speed and depth, where to push further and where to pull back. I’m just so excited to learn and play once more! Some specific positions I'd like to try are: Missionary, Cowboy/Reverse Cowboy, Doggy, Face-Off, Scoop, Table Top, and Champagne Room. No clue how common these names are, but I googled the positions and found that these matched what I wanted to try.

Have an orgasm on K's ass. I didn't cum at all during my first time, but that did NOT leave me feeling unsatisfied. I felt like I was on cloud 9 after that night, and rode that high all the way to work the next day. I think the emotional support I had felt more than made up for my lack or orgasm, along with the new sensations I experienced with a male partner, something I would've never imagined having even a few months ago. Sexting and trading on reddit with a variety of people really opened my mind and encouraged me to abandon preconceived notions and labels. If it feels good, it is good. Likewise, if you feel satisfied, you are satisfied. That being said, I've spoken with sexting partners in the past who very starkly underlined how important witnessing and causing a cumshot was to them, much in the same way I deeply appreciated seeing K cum from my touch over and over. That completely makes sense that some women would feel the same about watching their male partner cum, just like how I felt about K.

One thing I didn’t like or would have changed:

There’s so little to mention here that I thought about omitting this section entirely, but that would be disingenuous...and I found a way to stretch the one issue I had over a few paragraphs, so there you go. Perfect to me is a state of mind, not a list of percentages or a page of boxes all checked off, and I couldn’t even begin to describe my first time as anything but perfect. That being said, there were some things I was concerned about, even though my mind was either mostly or wholly fixated on the sex.

I suspected this, but confirmed it during that night: I do not have any sexual attraction to masculinity. Body builder, in-shape athlete, fit runner, average dude, dad bod, beer belly, ten-too-many pizzas, beard or no beard, long, short, or no hair, 18+ to over the hill...I am simply not turned on by a man. Classically, I would not call myself bisexual, but I don’t think having a label in 2019 is very important, for the following reason; I wasn’t turned on by my male partner, but the things he was able to do to me that I was comfortable with made me feel very good. And I'm attracted to trans women as well, who have the hardware but behave, look and sound very feminine, so I don't even know that there's a label to describe that kind of attraction...so fuck the labels! If it feels good, it is good, as I said earlier. But back on topic, not being attracted to M, and still really really enjoying the way M serviced my body.

He sucked me differently, fondled me differently, grinded on me differently. He gave me attention and touched my body in a different, but still completely pleasurable way. At first, with my eyes closed and both their hands and mouths all over me taking turns at my cock, I couldn’t tell who was who, but after a while I began to recognize their differences in technique and application. And I liked them both! Once I was enjoying both separate styles, it didn't even occur to me to think "Is this K or is this M?" because I really loved both applications of technique. But I worried, and still do worry, that my body's way of displaying my appreciation & arousal was...imbalanced.

Every time K was touching or sucking me, I was immediately hard, squirting out precum with every flexing of my cock. Nearly every time I was suckling her, kissing her, touching her, grinding against her, and just barely penetrating her, I was also absolutely hard, unless I was acutely focused on fingering her or rubbing her clit and maintaining my speed, pressure and technique. But for M, I'm so sorry man, when he was the one giving my penis the majority of the attention, I would find myself hard but not rock hard, shrinking down to a semi, or going entirely soft...and I mean entirely soft, down to a few inches, my pink little head completely lost in a tunnel of foreskin.

He said that he deeply enjoyed suckling and touching both hard and soft cocks, especially since he was circumcised and had a chance to explore a part of a man he lacked, but I began to grow concerned that I wasn’t going to be able to authentically share attention between both partners. After all, it would be pretty obvious if I claimed he turned me on and I was as limp as a week-old sprig of green onion. For some reason, this was a sticking point with me mentally, that I had to give as much to M as I was giving to K, even though I knew that I wasn't attracted to M, and he knew it too, and stated he was alright with that. Still, after we were already on the same page about it, I still felt guilty and selfish for being so enamored with every inch of K, but mentally appreciative and physically disinterested in M.

He dissuaded my concerns multiple times throughout the night, but I still feel that an arrangement where he is basically “stuck” giving my most sensitive areas attention and not receiving equal or similar attention from me while also not being able to penetrate me (I am not really comfortable with a masculine figure taking control of me, I suppose; Still trying to figure this one out in my head) feels unfair. Again, he told me this is not true multiple times through the night, and that he simply enjoyed sucking cock to the point where it made things more than satisfactory for him. During a moment where it was just the two of us, I even asked him what specifically he found attractive about men, and he reiterated his stance on sucking cock as the #1 thing he enjoyed. Despite all this, I still held reservations about the equity of attention & access I was giving K and M. And I still do, as I write this.

I really hope that he got enough out of the experience to satisfy him, because I would hate to return for more fun in the future and have him be disappointed or left wanting more while he’s allowing me and K to basically do whatever the two of us agree to. I worry that when we meet again for future sessions (And I REALLY DO want to meet again), expectations of me and my eagerness will rise in order to allow him to get more involved with my body and all its holes and openings. And I’m sorry to say that I am just not interested in giving another man attention like that or allowing a man to take control of me...even though getting some aspects of that attention is something I ended up really enjoying.

My good trans sexting partner who has now become my good and very close trans friend, we'll call her R, says that having an open mind and exploring like this is all about discovering your limits and your interests, and that every experience gives you something to learn about yourself, even experiences with poor or negative moments. And I like thinking about this "male equity guilt" I seem to have like that, because it reminds me that it's OK to have preferences and to have things you're not into, just like K sand she prefers not to do anal or to have deep penetrative sex during that time of the month, or how M would prefer to be submissive, but would be open to trying being dominant if the conditions are right. Totally fair, totally acceptable reasoning supports those feelings. I...maybe I need some time to think about my dis-attraction to men that way, as a totally acceptable opinion/standard. And if all parties agreed upon one another's interests and dis-interests beforehand, then...there's no problem, I guess. This one will take some time for me to consider before I can fully drive it home in my head.

Final thoughts:

This experience was so far and beyond what I had imagined it would be. The sensations, the emotions, the physicality of it all, the time it consumed, the complete comfort and adoration I felt from M and K...it's like a fictitious porn shoot! It just went so perfect, so clean, so right, so consistent, so fucking good, that I'm still reflecting on it like "Wow, that actually happened. You've got a one-in-a-billion experience that you'll be able to reflect upon until you're dust and ash."

I happily await our next evening of fun, and I hope that you got as much from my first time as I did.

Tags: bicurious, blowjob, deepthroat, emotion, virgin