My Saturday night of sexual misadventures

Discussion in 'Sex With a Large Penis' started by chillWEguy81, Apr 11, 2011.

  1. chillWEguy81

    chillWEguy81 Member

    Aug 7, 2009
    Likes Received:
    Seattle, WA USA
    It's often amusing to read some of the stories that people post here. Many of them I know are either fake, or greatly exaggerated for the purpose of storytelling. Being an English major, I can spot this out. I had quite the interesting time this weekend. While it will for sure not fit into a lot of people's views of what "big cock sex" is all about, it is quite interesting, quite funny, quite raw, and quite real.

    As I'm turning 30 in a couple of days, this weekend was a celebration of sorts. Next weekend will be to. I wanted it to be that way because I only turn 30 once, and 30 to me is more monumental than I thought it would be. It's like I'm not that young anymore, but at the same time I'm not that old either. I've been through a lot in life, and hope that the future will continue to bring me some grand life experiences. This Saturday night brought me one that I can't help but laugh about, but be fond of as well.

    To start off, I am genderqueer (or gender non-conforming) straight man. Technically I do crossdress, but not to where I try to look like a woman. While I present as a gender normative man on most days, I love the moments when I can bring some femininity into my attire. Combining it with my masculinity makes me feel where I'm supposed to be. I don't get the chance to go out like that all the time, but it was my 30th birthday and I felt like I was going to do what I damn well pleased.

    Fortunately, a lesbian friend of mine named Erin (name changed) gave me the perfect opportunity when she invited me out for a few drinks. Being that she lived on Capitol Hill (Seattle's LGBTQ and counterculture neighborhood), I knew that dressing how I wanted to wouldn't raise an eyebrow. So I dressed myself in a semi see-through Harley t-shirt (with a stretch nylon tank underneath for some modesty), black dress shorts, a pair of patterned gray Wolford tights, black heels, and off I went. We started off drinking at an Irish Pub not far from Erin's apartment along with her girlfriend Kate (name changed) and Carrie (name changed), a girl Kate worked with. I met Kate before and she heard of the way I liked to dress at times, but this was the first time seeing me out and she was astounded on how good I looked. She particularly liked my legs, which have the ability to rival those of leggy supermodels despite my overall tall and well built body. That of course led us to talk about a lot of my interesting gender complexities.

    Time passed, and we were joined by Erin's ex-boyfriend John (name changed), his new girlfriend Alyssa (name changed) and some other guy who I can't remember the name of. It was interesting to see John and and Erin interact because John was the only guy she ever dated, but thankfully no drama happened. I was also wondering how John was doing because he is genderqueer as well (and bisexual to boot) but going through a period where he wants to be strictly genderconforming and straight. I made no mention of it though because I didn't know if Alyssa knew about that aspect of him, and I do respect privacy. We all had a decent time talking and having a few drinks. After a while, everybody started disappearing. John and Alyssa left first, then Erin along with Kate. Being almost 1 meant every bar was going to stop serving soon. Being that I still wanted to stay out and try to get laid, it meant going to one place in particular: Neighbours.

    Neighbours has quite an infamous reputation in Seattle. It is a gay bar, but draws in droves of straight people and all types of social misfits. This is especially so because they're pretty much the only bar in the general area that stays open until 4 on the weekends and lets 18-20 year olds in once alcohol is no longer allowed to be served. The staff couldn't possibly ignore the amount of drugs (particulary coke, ecstacy, and crystal meth) that go through there. I often referred to the back alley to get into Neighbours as the "walk of shame". If you can think of any wild story that can go down at a bar, it has happened at Neighbours, and I likely contributed to some. It's the bar that everybody in Seattle loves to hate. They talk mad shit about it, yet will not hesitate to go there for some late night fun so long as they're pleasently under the influence. It is a bar that people of all sexualities and genders can get laid out of.

    I got there and had a couple more drinks. Since I had 5 or 6 drinks by this point, I knew I'd have to wait a couple hours before attempting driving home. I passed part of the time by indulging myself in my first cigarette in almost half a year. It felt so good, and yet I had no need to have another once I finished it. Talking to the drag queens there was interesting as well since they're always fascinated by the way I do gender. Yet my best surprise was later that night in the form of a very tall, sexy and spunky girl named Michelle (name changed).

    Michelle and I met out on the dance floor and we immediately took a liking to one another. Michelle was mesmorized by how I looked and loved how I playfully subverted gender norms, and couldn't keep her hands off my legs for the life of her. One thing led to another and we were soon making out. It didn't take long before Michelle invited me back to her place. I couldn't have been happier, and I'm sure that a lot of people got a kick out of seeing Michelle play around with my thong and grabbing my butt as we walked back to her apartment while calling me her hot piece of ass for the night.

    I had the nagging voice in my head telling me that I should have gone back to my car to get my condoms. I was sure that Michelle had some, but with my girth, I wondered if they would fit me ok. I didn't know what to do. Michelle was not the type of girl who would be impressed per se by hearing me say that I had to go get my Magnums because they're the only ones that will fit around my big cock. I was lucky as is having a pretty girl like her wanting to fuck me, and didn't want to ruin the moment by coming off as an arrogant braggart.

    We got back to her place, and sure enough it was on. It didn't take long at all before all of our clothes were off and we were in bed. Nobody who saw Michelle clothed would never have guessed how much of an amazing body she was hiding underneath her hipster clothes. If anybody saw how good Anne Hathaway looked naked in Love and Other Drugs, let's just say that Michelle would have given her a run for her money. I loved it. When we were getting to foreplay, I was perplexed on how unresponsive my cock was initially. Michelle was beginning to have her doubts as well. So I calmed myself down and instead of doing the moves that once worked when my erection response was on a hair trigger back in my teens and early 20's, I allowed myself to relax and them really get into the moment with Michelle. Like clockwork, my cock steadily rose to the occasion and had no problem staying that way.

    Michelle was quite taken back on my size and thickness. She didn't say it, but I knew she hasn't seen much cocks of my size, if at all. After a little more foreplay, we were in all out fuck mode. She did a very talented act of attempting to put the condom on with my mouth, and that's when I knew there were going to be problems. The condom wasn't able to get much past half my length before it was pinching off my circulation. I was going numb in my cock, but still had enough of an erection to fuck, and I was so horny at that point that I was going to make a valliant effort to fuck her brains out. We finally got to business, and I was in her. She alternated between moaning in pleasure and telling me to be gentle on her. I did, but I was also fighting a losing battle with the condom. It had killed pretty much all sensation for me at this point, which caused me to slip out several times. I coudn't keep up like that and we finally decided that sex without pleasure was a no go. We kept fooling around more for a little while before falling asleep.

    I woke up a few hours later, in awe of the beautiful woman I was in bed with. I woke her up with a kiss, and it didn't take long before we were making out like wild animals and wanting to fuck like there was no tomorrow. Michelle knew she had a breaking point where she would have let me fuck her without protection, and I knew I would have done it. She stopped us from getting to that point, and took the time to calm me down enough. Knowing she was a bit hung over, I went and got us both a glass of water. We drank it down and laid in bed for a while, having a great conversation about our lives. I liked hearing how she had a good job in the medical field, and she was of course fascinated about my past of being in the Navy, my current studies as a student, and what I wanted to do in the future. We ended up drifting back to sleep for a couple more hours.

    When we woke again, it was more of the same. We worked ourselves into another fuck frenzy, but that time we had a drawn out session of mutual mastrubation. I was in a position over her and gyrating my cock back and forth to her very skilled hand with one hand up against the wall and the other doing good work on her pussy. It felt good, but we both knew it was nowhere near as satisfying as good booty knocking sex we were both fiending for would have been. We wanted to so bad, yet our consciousnesses wouldn't allow for unprotected sex. We took some time to calm down once again. The next half hour had us snuggling and interrupting our conversation with drawn out kisses.

    11 AM rolled around and we had to go about our days. Michelle got a kick as she saw me dress back up in my clothes. We exchanged numbers with the plan to get together again, only to have the right kind of condoms for the next time. After a drawn out kiss goodbye, I left.

    As I was walking down the 12 or so blocks back to my car in my outfit from the previous night, I inevitably drew the attention of everybody from the weirded out moms pushing around their baby strollers to some gay guys who tried to cat call me. They more than likely had their assumptions about what I was up to, but I'm sure that none of them were accurate. And they would have likely been surprised at what I learned from that night:

    - I can express that part of me and can still find gorgeous women who find me attractive and desirable enough to invite me back to their place. And of course I will always surprise them when I show them the goods. In fact, using the element of surprise is preferred to just telling them.

    - While I don't have quite the hair trigger response anymore, I learned that I can get hard by just letting go and getting into the moment and the result is an amazingly powerful erection.

    - And most importantly, Never, EVER, leave my fucking condoms in the car again!! Better to have them and not need them than vice versa.

    That is all, for now at least. I'll post an update after it happens :cool:
  2. CuriousFem

    CuriousFem Active Member

    Nov 19, 2008
    Likes Received:
    Concord (NC, US)
    Yay! What a great night you had!
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