It started with a joke at a Halloween party. Emma and I had switched genders. She wore a man’s suit, and I wore a dress. One of the female party-goes, Lynda, quipped, “Now we know who wears the pants in the family.” My male hormones spiked, and I shot back, “I do the fucking in this family, Baby.” Misogamy was unlike me. Perhaps I had too much to drink. Emma was insulted and asked for an apology. I offered a half-ass one, “Sorry, Babe.” I could see in her eyes that she was furious. I tried to smooth things over with her and suggested we step away from the party to talk about it. Walking down a hall, we entered the first room that was available, what looked like a spare bedroom, closed the door, and we both sat on the edge of the bed. I apologized again, “I am sorry I hurt your feelings, Emma. What can I do to make it up to you?” I meant what I said, but dressed in the costumes, it was hard to stay serious, and I started to smile. Emma took this to mean I was continuing to make fun of her. She then said something that would change our relationship forever, “You need a good spanking.” The words seemed foreign to me. Neither of us were into that thing in the bedroom. She was serious though. I said, “If that will make things right.” I thought to myself what-the-hell, this could be fun.
Emma is not a petite woman. She played soccer in college and still goes to the gym three times a week to life weights. Once I agreed to punishment, she wasted no time pulling me across her lap, pulling the panties down I was wearing, lifting the dress to expose my bare butt, and she began to spank me with vigor. She didn’t strike with love raps. She intended to leave marks. The slapping noise was loud as she alternated one ass cheek and then the other. At first I could hold back any audible response, but after a dozen blows, I started to holler out each time she struck me. “Don’t have a smirk on you face now, do you Sweetheart?” As she continued spanking me, the dim light in the room brightened when someone opened the door. The interruption didn’t stop Emma from delivering her retribution. She continued for another minute or two, then she pushed me off her lap onto the floor. The person in the doorway stepped into the room and closed the door.
I recognized Brea’s voice, the host of the party, when she spoke, “Love spat?” The panties I had been wearing were still around my ankles. I pulled them up and sat on the bed next to Emma while she explained what had happened, how I had insulted her in front of another woman with the “who wears the pants in the house” quip, the “fucking” misogamy, and how I had been slow to apologize. Brea suggested I was the one who should be fucked. Emma replied, “Yea, I’m dressed to me the fucker tonight”, referring to her costume. Brea followed up, “Not quite. What you need is a strap-on.” Emma laughed, “Yup that is exactly what I need.” Brea smiled, left the room for a minute, and returned with a strap-on saying, “I use this on Brent (her husband) from time to time.” Things were spiraling out of control.
Emma took the strap-on from Brea, saying, “I have never even seen one before. How do you use it.” Brea shared her wisdom about pegging men while I shrank in stature next to her. “Stand up and I’ll show you how to put it on.”, Brea offered. Brea held open the straps, Emma took off her jacket, and Emma stepped into the straps while still wearing the rest of her costume, but before pulling the strap-on up to her waist, Emma said, “Wait, I have an idea.” She took the strap-on off as well as her trousers, then put the strap-on on over her boxers. Putting the pants back on, the dildo stuck out of her pants like a real dick. Both women laughed as Emma folded the dick up, zipped the pants, then unzipped them again to have the dick pop out. “Who’s the fucker in the family now, Buddy?”, said Emma as she gripped the plastic cock and waved it around. I looked at Emma and laughed. She got a serious look on her face and suggested I had not yet learned my lesson.
Brea held out a tube of lube. Emma asked, “How is it done?” Brea responded, “He’s fucked you before, right?” I nodded. “Then you know how it’s done.” Emma turned to me and asked if I was ready to be fucked. I protested but she said something that turned the tables, “You don’t have a problem fucking me, right?” She was obviously referring to the stupid comment I had made earlier. What followed was an ultimatum, “If you don’t take this cock, I will never again take yours.” My first instinct was to walk out of the room, but I really wanted to stay with Emma and I wanted to make things right with her. I suppose deep down I knew I deserved what was about to happen. I agreed to be fucked.
Emma asked Brea what position was best for pegging and she suggested doggie. “It’s the most humiliating position.” Emma ordered me to get on all fours on the bed. After I assumed the position, she pulled my panties down again, flipped the skirt up over my back, and started applying lube to her cock. Brea suggested she loosen me up first. Emma didn’t know how to do that and Brea offered to help. Putting on a glove and lubing it up, Brea stuck her index finger in my anus. It was the first time I had ever been penetrated by anyone and and now the first time it was a practical stranger who was doing it. Brea added digits while twisting her fingers back and forth to enlarge the hole. After getting three fingers in, Brea said I was ready. Emma held me by my hips and pushed her cock into me. There was some initial resistance, but once the head had penetrated my assshole, she pushed the rest in with a single thrust. Not waiting for me to relax, she started fucking me enthusiastically. In the middle of fucking me, Emma leaned over to Brea and asked her to “document” my fucking. Brea took out her phone and started videoing. After ten or fifteen minutes, Emma pulled her cock out of me, and she told me to compose myself and return to the party. I couldn’t look either of the women in the eye as I pulled the panties up and left. I could hear Enna and Brea giggling as I left. I could feel lube soaking my painties.
I went straight to the bar and poured myself a large glass of whisky. Finding myself a quiet place in the corner, I reflected on my experience. I had gotten what I deserved. I needed to reassess my attitude. After ten minutes or so I went to look for Emma. I found her with Brea and Lynda, the woman who earlier in the evening had witnessed my boorish behavior. Brea was showing Lynda the video she had shot. I was unaware of the video, but when I looked over Brea’s shoulder at what she was showing, I knew exactly what was happening. This was the last element of my reckoning. The three women turned toward me. They had smiles on their faces. They seemed to be waiting for me to say something. I understood what they were expecting. I turned to Emma, “Thank you for correcting my behavior.” She acknowledged my comment but seemed to expect something more. “And thank you for fucking me.” The three women acknowledged my change in attitude and Emma made the last comments before we started getting ready to go home. “Sweety, Brea gave me a party gift.” She took my hand and placed it on her crotch. She was still wearing the strapon. She patted me on my bottom as we made our way to the front door.