Tag: Prostate

The Secret International Society of Sissified Youth (SISSY) Order [Trans][Submissive][Sissification]

I am a card-carrying member of the Secret International Society of Sissified Youth (SISSY) Order. Well it’s not really a card but, more of a ring. This is my story of how I became member. I’ve been with the Order for 10 years of service, 8 of which were great. I’m not sure if I’ll make it to retirement but this is my story of how it all began.

It all started really when I was 11 and began dressing in my Mother’s clothes. I didn’t know what it was at the time but, being in women’s clothes just felt right. That might have been due to be molested by a neighbor during that time period but, I don’t look at that in a negative light. I believe he was just helping me find the way to my true self. Who knows, maybe I was asking for it, god knows I would do it all over again the same way if given the chance. Read more »

[MMF] My ass is no longer a virgin.

*I’ve posted quite a bit on the Chastity subreddit and just the other day I came across this sub and I figured my story was worth sharing here.*

I’m a male who’s kept in chastity 24/7. If you’re not familiar with the practice this goes a long way towards explaining it:

*(edited slightly from Wikipedia) Chastity belts may be used as part of a practice of orgasm control, to prevent the wearer from engaging principally in sexual intercourse without the permission of the dominant, who acts as “keyholder”. A chastity belt will also prevent other sexual activity such as masturbation and oral sex involving the wearer’s genitals.*

*The putting on of a chastity belt, by a partner, is an indication of the dominance by the “keyholder” over the wearer’s sexual activities. By accepting the chastity belt the wearer accepts surrender of control over their sexual behavior to a partner, who may grant permission to the wearer to engage in sexual activity by removing the belt. The dominant may decide when, where, how, how often, and even if, the submissive is allowed sexual release.* Read more »

[MMF] My first unexpected bisexual threesome

Please excuse the grammar as I’m typing this on my phone. This is a true story about this past weekend with my girlfriend and her good male friend. I identify as a straight male, very masculine and have only ever dated women. I’ve had experiences in the past in threesomes and orgy’s but have never done anything sexual with a man, until this weekend that is.
My girl and I rented a cabin in the mountains for the long weekend. It’s been a year since we’ve gotten away and we just wanted to get away from the stresses of work and kids. One of her male friends from college was going to come up for the day and hang out with us. We’ll call him Dan for the purposes of this story. About an hour after we checked in I heard a knock at the door. I opened the door and greeted Dan with a firm handshake. He was a pretty tall guy, I would guess about 6’5 and 200-230 (same as me with a few inches in height). My girl squealed and ran over to lay a big hug on him. We all talked for a while, they caught up and I got to know him better. I had always heard stories about him from college but never anything romantic.
The night carried on and Dan went to his car to get some things that he had for my girl Kate. He came back carrying gifts, a large bong and a bag of weed. Kate and I didn’t smoke too much weed but we decided that we would partake with him since he did offer. About 4 good hits later and everyone was feeling good, very relaxed and a bit amorous. I hadn’t seen Kate high before, but apparently it cranks her libido into overdrive. She proceeded to tell me how turned on she was and what she intended to do to me later; I was really digging high Kate. It was getting late and we invited Dan to stay the night since he was high as a kite and wasn’t in any shape to drive.
This particular cabin had a four person hot tub that Kate and I intended to take full advantage of later that evening. After we finished our dinner we all decided to head for the hot tub. Kate invited Dan to come out and soak with us. I was a little perturbed as I wanted to get freaky with my girl. Dan started stripping off his cloths right in front of us and we followed suit. Dan was in pretty good shape and was packing some serious lumber. I’ve always had a thing for cocks, just looking at them, and Dan didn’t disappoint. I would say he was 7-8 inches and thick. We ran outside and jumped in the hot tub since it was 18 degrees.
The conversation flowed and we continued to partake in the super strong weed that Dan brought. We continued to hit on the bong and eventually all of our heads were swimming. Kate started feeling around under the water where she found my cock hard as a rock. I felt her slowly begin to stroke it under the water which drove me crazy. I’ve always had a bit of an exhibitionist streak so I was enjoying the covert action under the bubbles. I could tell that Dan knew what was happening but he kept it to himself until I was almost ready to cum. He glanced over at Kate and asked if she intended to leave him out of the action? Kate has always been a bit vanilla and a proclaim monogamist so it surprised me that her good friend would hit on her. I was right on the edge and his comment pushed me to the point of no return. I felt my balls tighten as I stood up to cum. In an instant move Dan moved to our side of the hot tub and took my cock into his mouth. I was in complete shock but it was too late. I came so hard filling his mouth with ropes of hot cum. He swallowed most of it but some ran out of his mouth and down his chin.
I stood there with my cock in Dan’s hands and my jaw on the floor. Kate was shocked a bit too, but she wasn’t surprised. She failed to tell me that Dan was bisexual bordering on full on gay. We both took exception to his violation of our trust without even asking. He smiled as he wiped the cum from his face and quickly apologized. He said that he was so turned on that he couldn’t resist taking my load. Kate told him that it was not okay and that I wasn’t bi. To be honest I didn’t hate it but would have liked to known what he was going to do before he did it. That ended our evening in the hot tub as we all retreated to the warmth of the cabin. The weed had made us all so tired that we all passed out rather quickly. Read more »

How I lost my virginity to a college threesome. [MFM]

I lost my virginity my freshman year of college. It happened in the spring semester, early February, 2011. To this day, it was probably one, if not the best, college experiences I had. Not only did I lose my virginity, I lost in in a threesome with multiple rounds of raw sex. It was a Friday night and I was out looking for a house-party with my roommate Jay. We found one that was pretty legitimate, but nothing too crazy. After a few beers each we started chatting with these two girls our age that were from a dorm building across campus. We hit it off immediately, and I was surprised at myself for carrying on a carefree conversation with this cute girl Kylie. The other girl’s name was Taylor. After a while of talking, the four of us, Taylor saw some other friends and went over to them. It was just me, Jay and Kylie hitting it off, and she was getting kind of playful and flirty. Just as we were finishing off our second beers and feeling good but not drunk, cops showed up because of noise complaints. Read more »

After the Gym Pt. 2 [mmm] [anal] [exh] [Msub] [cuck] [mast] [oral] [swing] [bi] [gay]

I think the answer must have literally spilled out of my mouth – or at least my body language properly reflected a resounding ‘yes.’

 

Jeremy was smiling now too, “Man,” he said, “awesome. Lemme just send Michael a text and tell him you’re coming over?”

“Uh,” my heart was already pounding, and my legs felt a bit numb from the work out, and I sort of sat down on one of the benches lining the outside of the showers, “yea man yea.”

“You good?” Jeremy asked, stepping into the locker room briefly to fetch his phone.

“Just excited,” I laughed, “and tired.”

 

He popped back into the room and sat down beside me on my right.

 

“I sent him a text, we’ll wait a bit and see if he replies,” Jeremy said, looking at my cock. I could see precum already drizzling out of it steadily. “You’re *really* excited.”

I laughed, “what gave it away?” I felt a bit short of breath and felt I couldn’t have stood even if I tried – my whole body was tense with anxious energy, but in a good way. Read more »

After the Gym Pt. 1 [mm] [bi] [gay]

Steam from the shower room always hit’s like a vapor. This late at night there’s rarely anyone at the gym so I don’t feel too awkward staying in and showering. The alternative is to freeze my ass off at a bus stop at -20 degrees Celsius only too stew in my own sweat on the 30 minutes bus ride home.

 

Had it been a busier night, like on the weekend, I’d have taken the journey. During the week however, to many people working square in the morning usually leave the gym by 10, and those left are those of us working afternoons or not working at all. I was the latter, hopping from casual position to casual position and trying desperately to ward off boredom by filling my off time with anything. These things included gaming, jerking off constantly, and going to the gym.

 

Now, I’m hardly what you’d call a ‘gym rat.’ My whole life I’ve been blessed with a fast metabolism and a low competitive drive, so I’d never really been one for self improvement. Standing at 6’4″ as an adult, I was fairly slim but didn’t have a lot of muscle to me. After my last break up and seeing the guy my ex girlfriend had ended up with, I decided I needed to do something to boost my self-image and confidence. Filling out my figure ought to be the thing, I thought. Read more »

[M]y Wi[F]e Lucy Finally Gets What She Wants. [Pegging]

Hi again back with another short update for you guys about my adventures with my wife Lucy, this all happened last weekend. We had booked a hotel in the city for just the two of us and left the kids with my parents for the weekend, so that we could get the last of the Christmas shopping done. We shopped all day Saturday and by the time evening came we were both exhausted from battling the crowds in the shops. Lucy had a table booked at a restaurant near to our hotel, I wanted to order room services and hit the hay. But Lucy soon changed my mind when she whispered in my ear “If you go to bed this early you will miss your surprise I have planned for this evening” while slowly rubbing the growing bulge in my jeans. So we freshened up and headed out on the town for the night, after 2 bottles of wine with dinner we made our way back to the hotel. But stopped off for a quick drink in the hotel bar before making our way upstairs, but one quick drink soon turned into 4 or 5 and we were both starting to get a little drunk. Laughing and flirting in the bar, our hands exploring each other under the table. I could tell the other guests were looking at us but we both didn’t care. Eventually we made our way out of the bar and headed for our room. We made it as far as the elevator before Lucy jumped on me, making out violently and started dry humping me. Ding! The door opened and we stumbled to our room, almost tearing each other clothes off before I could eventually get the door open. Read more »

Have my Daughter, Pt. 3 [Mff] [oral] [anal] [squirt] [prostate] [cumswap]

Hannah was turning into quite the sex freak. She texted me three times last week asking for things to google and learn about. Now, if you don’t remember, Hannah is the 19 year old daughter of my gym friend, Abby.

Now, I’m 32 years old and Abby is in her mid-40s and decidedly not into younger guys. But she was worried that her horny daughter would get mixed up with the wrong crowd, so she basically sent me in to teach Hannah a thing or two.

Hannah was totally receptive and in exchange for getting to bang a 19 year old, I had another responsibility: Teach Hannah to respect herself and show her what a gentleman looked like.

So, every week or so, Hannah and I would go out on a little date. I’d hold doors for her, pay for some of her meals (but the feminist in me and her mother insisted that she pay for some meals, too).

On this particular outing, we were sitting in outside at a sushi restaurant, laughing, having a good time, when suddenly, she sprang an idea on me: Read more »

[Long] [MMF] [MFM] [Threesome] [Cheating] There’s Something About Mason (and Krystal)

>I’ve never written anything like this or posted anything publicly before, but I’m considering putting these experiences into an e-book and publishing it, so I’d really welcome everyone’s feedback.

#**There’s something about Mason (and Krystal)**#

—
**Part one**
—

Admittedly, this was going to be my first threesome. I’ve slept with both genders and everybody in between, but never at the same time. It’s not that I’ve never had the opportunity; it’s that I’m just quite picky with my partners and when the opportunity has arisen before, I’ve just never felt ‘it’.

Whatever ‘it’ is.

Mason was an interesting guy though – he was about 26 years old and after graduating from some university with an MBA, he was through his second year of a “Graduate Scheme” for a large multi-billion pound, worldwide organisation. He wasn’t senior within the business at all, but he was certainly rubbing with shoulders he felt would get him places, eventually.

The funny thing about Mason is that despite his “high flying” career (and perhaps his misplaced sense of grandeur), his hyper-masculine attitude and his kind-of-cheap-but-well-fitting-suit, we had met on Grindr – the male orientated hookup app – his profile was brief; he was a straight man who wanted to experiment with other men, despite being in a long term relationship. Read more »

[MF] Christmas Present

I always hated going to my girlfriend’s home for Christmas. Imagine being in a household with two upper-middle class snobs who like to think that their high-class and knowing that for every second you talk or see them, they are judging the hell out of you. And along with that, constantly doubting their daughter’s choice in being with me. Fuck them.

…. however, I’d be a liar if I said I completely hated it. Growing up in a cramped, middle-middle class home where three people shared a tight bedroom, and a working household of five shared a single bathroom, the living situation I experienced in the home of these two snobs made the holidays somewhat bearable.

While I’m technically supposed to sleep in the guest room, the home is large enough that her parents don’t bother checking and so I spend alot of my nights with her in her room. Often, we would spend these nights having rough and angry sex as I vented my frustrations by hammering her pussy.

This Christmas was interesting though. Read more »