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A Date With [M]yself [20’s][crossdressing][solo][feet][anal]

Please go easy on me, this is my first story! 🤭 I hope you enjoy! 😊❤

For context I’m a 5’5″ bi-curious male weighing in around 200 pounds, a little on the chubby side yet still firm. I looooove crossdressing, but am waaay too shy to go out dolled up! Every now and then I get the strongest compulsion to dress up and go to town on myself, and this was one of those times.

I woke up that morning determined; that night I was going to treat myself to a date and have a little fun afterwards. My body was still smooth after shaving a couple nights ago, and my toes were painted a lusty glossy black. In the mirror I looked so femme, yet was slightly bummed I couldn’t flaunt it. With a pout I showered up and put on what femme clothes I could; I wore a toe ring on each index toe, a nude thong and nude sheer pantyhose with a cute silver anklet on my right ankle. Over this I slipped on my boy clothes, and headed out the door to start my day. Read more »

Sample from ‘June at Home’ – couple chatting bed – [M42][F40][adultbreastfeeding][adultsex]

“Yes, rekindling our relationship was a bit, well rekindling is wrong for a start, reigniting is a more accurately descriptive word, but even as horny teenagers I don’t think we were ever this passionate.”
“I think we were, you were,” reflected June. “I think that we just didn’t know enough to get the most out of each other. Your ultimate was for me to have an orgasm before you had yours. Neither of us imagined having several. I’ve changed through. I’ve changed since we got back together. Suddenly I’ve become multi-orgasmic.”
“You mean you weren’t before.”
“Sweetie, suckle, please.”
I assumed the position and latched on. The milk flowed very quickly. June must have been waiting for me for hours.
“Yes, Sweetie, that’s nice. I don’t ever remember having more than one when we used to make love. I know sometimes you’d finger me and I cum, then we’d make love and normally I’d cum again. And all those twenty years, even when I used a vibrator, I’d use it until I came and then stop. No, I think the first time I came more than once on a single bonk was Day Two, at my house. How momentous was that, that I remember it. It was suddenly like blinkers had fallen from my eyes. Once I’d decided I wanted sex with you and that I was finished with Barry, well finished ever having sex with Barry, something inside me was released. And this is what I don’t think I’ve ever told you, not in these past nine months. Well, after we made love at the farmhouse, that first time, I told myself I was never having sex with Barry again. Even if you and I didn’t happen, even if I stayed with him, I’d be celibate rather than ever have him come near me again. The moment you pushed inside me, I thought that.
Actually, I thought, bloody hell, this is what I’m made for, not Barry’s waste of time. You see, I’d settled for what I knew was inferior. Looking back, I have no idea why. Why didn’t I leave him during the honeymoon? I could have just got a flight home the next morning. If anyone asked I could have said he was hopeless, I could have told my girlfriends that it turned out he’d got a tiny cock, I’d have got tea and sympathy. Mother, ah mother, what could I have told her? I don’t know, I did try and she just said I’d made my bed, I had to lie in it. Makes me wonder what my father is like. But I didn’t. I bottled out and put up with him, Barry, not my father! Twenty ‘kin years. Twenty FUCKING years of my life, when my body was young and at its peak, I wasted it in misery and disappointment. No, don’t stop. Keep feeding. I can’t change that now, you are right, what is gone is gone, and the past is the past. I don’t feel sorry for myself, I feel mad at myself. I know it gave you time to go and get all this experience that you bring back to this relationship, I can see that. And sometime, when you are not suckling, you must try and tell me how much you discovered and how much you were taught. I’ve taught you that you can be multi-orgasmic, which gives me a sense of pride and empowerment. Even though I’ve nearly damaged you by going too far, it means I, June, did that. Thirty-nine years I thought that sex and love-making were things I received. These nine months you’ve blown that preconception to smithereens. If I suddenly have an idea for something new to try, I know I can suggest it and you’ll want to try it. Not, you’ll go along with it. You’ll want to try it just because it is new but also because I’ve suggested it. I really think you’ll try anything I suggest. That’s so liberating.” Read more »

Distractions Under the Desk [F/M 20’s]][Kitten][Oral][Creampie]

I sat down to write a moment ago and a most welcome distraction joined me for the endeavor. She nuzzled against my shin before finding herself a comfy spot between my feet, pawing at my legs in an effort to get my attention. She poked her head up between my legs when I didn’t give it quite fast enough.

“Can I help you?” I couldn’t help but grin and laugh as I said it. I took a moment to gently place my hands around my girlfriend’s neck before tracing a line to her lips, meeting them for a sweet moment before I pulled her in for a hug against my cock.

“I thought I could keep this warm for you, sir.” She suggested, pawing at my dick through my jeans. I was happy to pause writing for a moment to remove my bottoms.

I started to get hard just undressing there, admiring the curly haired goddess under my desk. She was quick to grab my cock as I sat back down and the glee that washed over her as I got ever harder was just. so. fucking. hot. She was just holding my dick, gazing at it lovingly. She looked up into my eyes and gave my shaft a kiss, pressing her face up against me after, “Whatcha writing?” she asked. Read more »

Succubus Short Stories Ch. 6 [M20/F20] [Fiction] [Sex Toys] [Hand Job] [Sex]

“Here’s your coffee sir.” the kind waitress said to me as she handed me my drink. “Thank you,” I said tiredly, I was at one of my favorite coffee places, I like to come here to relax after stressful days at work. Which with the job that I have, I’m here 24/7, but it pays extremely well so it’s hard for me to complain. I was sitting at my booth, reading a book and enjoying my coffee when an older-looking woman sat down across from me. She didn’t have a drink and seemed to just be staring at me. She had long, brown, perfectly curled hair and gentle brown eyes. She was wearing a turtleneck with an open gap just above her chest showing plenty of cleavage. Her breasts were huge, if I had to guess, I’d guess that she was an F cup. Her outfit hugged her curvy figure tightly, and you could tell she liked showing herself off. She had this…. aura about her. I can only describe it as a caring motherly gentleness to her demeanor which completely goes against what her outfit was saying “Is there anything I can help you with?”, I ask her, “Just thought you might want some company.” she said. This isn’t the first time something like this has happened, many times random people sat down with me when I was reading alone to just chat with me about anything, I don’t mind it, I’ve met some very interesting individuals doing this. Read more »

All About Her Part 4 [M18-F41] [Cuckolding]

Once Sid went in and shut the door I could visualize what he’d most likely been dreaming of awaiting him somewhere in that house. As I dried and put away the tea dishes I knew by now she would most likely be already giving him the ride of his young life along with all the trimmings. True to form she’d do her best to drain every ounce of cum he could generate and wouldn’t return home until he was unable to continue.

I popped a couple of sausage rolls into the crisper knowing she would probably be famished from the “workout” when she made her way home. I then cracked open a Pilsner, headed for my upstairs office and buried myself in work. When I finally completed my reports and handled a slew of emails I realized I had lost track of time. It was well after midnight and Mags hadn’t returned. I grabbed my phone and saw she had sent me three messages. Read more »

The Dancer, Part Nine [F19/F18/some M19] [Dub-Con] [Exhibitionism] [Reluctant Lesbianism]

**PART NINE**

I had to do anything Heather said.

Since I barely knew the girl, I had no idea what to expect. Was this belated revenge from high school, just because she didn’t get to star in as many dances? Or was it just opportunistic bullying, just because she could? At the end of the day, it didn’t really matter. I was at her mercy.

Heather began with, “Take your skirt back off.”

She said it so casually, save for a hint of smugness. The tone of voice itself made me want to scream at her, as did the idle smile on her face, but I couldn’t do anything but obey. My reputation and my future depended on it, as I needed my instructors as references down the road. I narrowed my eyes in annoyance, to at least show that I wasn’t happy about this, but did as she said. With none of the bravado from the first time around, back when I was playing the part of the featured stripped at Autumn’s party, I merely yanked the garment down and let gravity finish the job. Assuming that she’d want it all the way gone, I stepped one foot at a time out of the dark gray number that was pooled around my feet for the second time in less than ten minutes. Read more »

Lights Out! [M29, F29] [Edging] [Blowjob] [Biting] [Softcore]

The lights flickered. The tv they had not actually looked at in 10 minutes flashed off. They both sat with their feet on the coffee table, staring at their phones. One of her legs casually draped over his. At the first flicker their eyes darted up, then looked at each other.

“Was it supposed to be this windy?” she asked. The lights went out again and did not come back on. Her phone disconnected from the internet it refused to load the article she was so close to finishing.

“I didn’t think it was going to be this bad, but you never know. It is New England” he replied, pushing back one of the curtains to look outside. The sun set hours before but the streetlight illuminated the blizzard outside. The snow blew in drifts down the sidewalk and covered the cars so they were almost invisible.

They put their phones down for the first time in a couple hours. She leaned her head against the back of the couch and looked at him.

“No lights, no internet… whatever will we do with ourselves” she grinned. Read more »

First Time at a Swingers Club [M35, F30, M30]

Jane and Mike showed up at the swinger party not knowing what to expect. It was held in a large house that was repurposed for different events. The house had a main area with different sections, dance floor, bar, and lounges. Down the halls were an assortment of rooms.
They mingled and found the people they met friendly. But it was a bit of a new experience for them, so they mostly used it as an opportunity to talk to people in the lifestyle and see if it was right for them. Not that they were not interested in the people they met. They liked at least one couple they met and indeed Jane got the wife’s number even though she felt a bit jealous seeing the way her and Mike were looking at each other. A few single men made an impression on them. Any single guys at an event like this would have to be invited, so they were the kind of attractive polite gentlemen you would expect to get an invitation. But they felt reluctant to just jump in and go home with anyone. However, the evening had excited them both. Mike enjoyed seeing so many men interested in Jane. It got his imagination going. Jane enjoyed the attention. Of course Mike liked that some women showed some attention to him. Jane felt a bit jealous when she saw this, but it also lit a competitive fire in her. So even though they were not looking to play with anyone else tonight, they could not wait to get home to have sex with each other.
They found an empty room and left the door open. Jane had an exhibitionist side and liked the idea of people catching a peak of them. The atmosphere had gotten them both worked up. They kissed and sucked on each other’s necks as they made their way onto the bed. Mike caressed Jane’s body. They pulled each other’s clothes off until soon they were naked. Mike sucked on Jane’s nipples while she played with his. Around this time they noticed one of the guys they had talked to earlier standing in the doorway watching. They did not acknowledge him, but they did not ask him to leave either. Jane and Mike continued like this for another minute. Then Jane began to stroke Mike’s cock. She could feel it becoming hard in her hand. Mike reached down to rub Jane’s clit and he could feel she was wet. Around this time the man who had been in the doorway had entered the room and sat down in the chair next to the door to watch. The combination of this and having her clit rubbed excited Jane. She had Mike lie down then she sat on his face and sucked his cock. While she was going down on Mike she snuck peaks at the man in the chair. She could see him rubbing at his pants. No doubt he was getting hard watching the scene in front of him. This was getting her even more worked up, so she stopped sucking Mike’s cock so she could sit up and be in a position that was more likely to make her cum. Mike grasped her ass more firmly as she did this. It was then that she noticed the man in the chair had pulled his cock out and was sitting there stroking it as he watched them. Seeing how hard the guy got watching them excited her even more. Then Mike began to stroke his cock with one hand while he played with Jane’s nipple with the other and the experience heightened even further. Jane looked into the man’s eyes longingly as she watched him move his hand up and down his large cock. Being pleased by one man while another watched was something she could only stand for so long before she came. After she rested on Mike’s face for a moment, Jane got up and Mike directed her to get on her knees facing the man in the chair.
Jane was very wet and Mike entered her easily from behind. He began to fuck her, slowly at first. But he very soon picked up speed. He grabbed her ass and made her moan. By this time another man they had met earlier was watching from the doorway. Jane eyed him seductively and he took a seat in another chair next to the door. At this point Mike was pounding her quite hard. She looked up at the first guy and motioned for him to come closer. He stood up and walked over to Jane. The guy pulled his pants completely off and now that he was so close Jane could see he had a very large cock. She had never experienced a cock this big. The sight of it was alluring. She wanted to touch it and to put it in her mouth. The man positioned it right near her face, but waited for Jane to act. She placed her hand around it and felt its girth. Then she slowly started sucking it as she held the base with her hand. Getting fucked by Mike while she had this large dick in her mouth felt dirty, but amazing. Jane wanted to feel this big cock inside her. She had Mike pull out of her. She laid down on her back and directed Mike to lie next to her. The guy whose cock she had been sucking put on a condom and entered her waiting pussy. Even though she was rather wet, it took her a moment to take him all inside her. She exhaled deeply as he thrust inside her. Mike found this very hot and rubbed his cock as he watched more and more of this massive cock fill Jane’s pussy. Once she had taken it to the hilt Mike began kissing Jane and rubbing her nipples. She kissed him back deeply. Then Mike began to suck on her nipples.
At this point they noticed that the other guy had unzipped his pants and was stroking himself while he watched from the other side of the room. A couple who was passing by had also stopped for a moment to watch and they were whispering to one another, obviously enjoying the scene. The guy with the big cock started to fuck Jane harder until she began to arch her back and cling to the sheets. She held Mike’s hand tightly as it became more intense. When it did not seem Jane could take anymore the guy came, his large member throbbing inside Jane’s pussy. He got up, got dressed, and walked out the room. Jane directed Mike to lie on the floor. She sat on his face so he could lick her freshly fucked pussy. It was so hot to lick her pussy after another man had just been inside her. Then she motioned for the guy in the chair to come closer. He dropped his pants completely and Jane grabbed his erect cock and put it in her mouth. He had a good size dick, but after the last one it was much more manageable. She sucked and stroked him. Before she knew it he was cumming in her mouth, this set her off and she came again as well.
Jane got off Mike and gave him a long deep kiss. At this point he took her on the corner of the bed and began fucking her. By now the guy had left the room and a couple had sat down in the chairs by the door. The woman had her hand in her pants and was rubbing herself as she watched them. Before long the man had removed her pants and was going down on her. This was so hot for everyone. Mike fucked Jane hard until they both came. Jane and Mike cleaned up then cuddled for a few minutes before they got dressed and went home (but not before Jane found a bathroom).

Stay at my side Ch.30 [18M/18F][Friends to lovers][Planning a date (little stressful)[mentions of: Sickness and minor reluctance]

Chapter 30: Preparations

“Matt you still owe us an explanation!” I’ve been able to flee from this for now almost four days but I guess that was now over. Cornered in the gymnastics hall, I sighed and looked into the faces of my friends. Curious wasn’t even close to what they were. They would probably torture and kill me if I didn’t tell them about what happened between me and Casey.

“Okay guys, I give up.” I wouldn’t tell them everything but I couldn’t deny that something happened.” “I began by summing up what has happened before they caught me through voice chat but left out the part where we kissed. None of them knew that I had a guest room so I gave that as a reason why we shared a bed. “And with sharing a bed I mean only sharing and nothing more.” Read more »