Disclaimer: This story involves themes of pegging, BDSM, and femdom.
_________
Recap: After many unsuccessful dates, Matt was ready to call it quits, until he matched with Jessica. After a few months of only texting, Matt knew she was special. Finally, they were able to meet in person, and though he was afraid he was getting catfished, Jessica was everything he had hoped. After meeting her son, he knew this was the life he wanted. This was everything he had been looking for. But there was a catch. Jessica told Matt of her abusive ex-husband, and how she went to counseling, where her therapist suggested femdom. After researching, Jessica discovered pegging and femdom, and she had to be the one in charge in the bedroom to help her feel safe and secure.
________________
That was the best sleep of my life. Jessica and I slept in as we recover from the previous night's escapades. In Jessica's bed, we fell asleep with her in my arms.
Jessica, wearing a large T-shirt, and still in her fishnets from last night, sat on the edge of the bed, rubbing my back.
"Hey sweetie, it's time to wake up. I got brunch ready."
I let out a loud grunt as I stretched. Slowly I got out of bed, feeling just how sore I was from last night. My thighs burned from the positions I was in. Man, my bottom was sore. It wasn't so much pain but rather felt like muscles I've never used before had been worked out. Jessica handed me my boxers and one of her baggy T-shirts
"Go ahead and change. You look ridiculous," she said with a smirk, teasing me about being naked except for the thigh-high socks she made me wear to bed.
I followed her to the kitchen, eyes glued to her fishnet-covered ass, then drifting down to her feet as she walked on the balls of her beautiful feet.
"Wow, drinks and breakfast. Guess you are a keeper," I said, as she ate together.
"We did use a lot of energy last night, we need the energy boost." She said with a wink. After a moment of silence, she continued. "I know last night is still pretty fresh, but I thought maybe we can talk about it later tonight. So we can just enjoy each other's company."
"Yeah, yeah, that sounds like a good idea. Do you have any plans for today?"
"Nothing on the agenda, just got to pick up Aiden later today."
After finishing our meal, I helped put up the dishes, appreciating this new dynamic with Jess. After cleaning up the kitchen, I headed to the bathroom to take a shower and clear my head. I loved being here with Jess. This is what I wanted, but I was still reeling from last night. Jessica looked absolutely amazing dressed up in black, but the pegging and submission didn't come naturally to me. We definitely needed a heart-to-heart tonight, because I don't think I could do that again. Conflicted would be an understatement.
I returned with a clear head to find Jessica looking distraught in the living room.
"Hey, what's wrong."
"Um, they think that my dad had a stroke. He's in the hospital, and I have to-." Her voice cracked as she tried to fight back tears, quickly losing her composure. I wrapped her in my arms, squeezing tight.
"Sweetheart, I'm so sorry. I'll help you get ready, so you can go be with your family."
As bad as I wanted to be there for Jessica and her family, I knew this was a family matter and didn't want to impose. If she wanted me there, she would invite me.
__________________
She dropped me off at the bar where I had left my car after a night of drinking. I kissed Jesse and told her to call me if she needed help with anything or if I could do anything for her.
The drive home was bitter-sweet and gave me time to contemplate everything. Last night was my first glimpse into the world of Femdom. I had been bound and pegged, just like Jess said. And even though I did have some fun, I still couldn't wrap my head around what a relationship would be like as a sub.
Being able to worship her feet was amazing, a fantasy come true. And the way she dressed and ordered me a round was a big turn-on. I didn't mind being tied up, but the parts I struggled with were pegging and eating my own cum.
I wanted to please Jess, but having a foreign object in my ass was just embarrassing to me. And a part of me still thinks it's gay. Jess was right, anal play for men was very intimidating. And the humiliation of cleaning my own cum just wasn't something that I could look forward to. I knew Jess could sense my hesitation and my indifference to the events of last night, and would have to be something we talked about.
I couldn't imagine living life without Jess, but I don't know if I could keep this up once a week, even once a month. I know this was a hard stance from Jess, so it was really up to me. Could I learn to swallow my pride, or was I willing to admit that this was too much for me? If this was going to work, she would have to compromise too.
It was difficult not to check my phone constantly. I wanted to give Jess time to herself and her family to think. She would text me when she wanted and when she had time, and I didn't want to bother her.
With my conflicting thoughts about our sex life and my sympathy for Jess, I strived to keep myself busy for the rest of the day. Night had come and Jess still hadn't texted me. So I decided to give her one text and head to bed, ready to work tomorrow.
Matt: hey babe, just wanted to check up on you and see how you're doing. I hope everything works out. Just let me know if there's anything I can do for you and your family, like if you all need food or anything. Good night, babe
I woke up disappointed not to find a text. Reluctantly, I got dressed for work, where I check my phone every hour. It wasn't till after lunch that I finally received a text.
Jess: hi, I'm so sry about last night. Dad wasn't looking good for a while, and I was pretty busy with the family. Dad's doing a little bit better but is still in rough shape. They're struggling to keep him stable. Thanks for checking up on me, I'll let you know if we need anything.
Matt: no problem, babe. Just want to make sure you take care of your family.
Jess didn't text back for the rest of the day. I hated knowing there was nothing I could do, and I hated myself more for being selfish.
Matt: hope you're doing OK, I'm always here if you need me. Hope to hear from you soon.
Monday night was the last time that I heard from Jess. I left a few messages a day with no replies. I decided to send a bouquet to her house. Contemplating going over there, I thought it best not to. She would reach out to me when she was ready. Thursday came and there was still no reply. I started getting desperate.
Sure, she was probably stressed over her father, but what if it was something else? What if she sensed my hesitation that morning? I knew I was a little reluctant about what she wanted from me and I wanted to talk about it, but what if she already decided I was a lost cause? Fuck! I hated these constant mood swings. Depression, anger, spite, sorrow.
I called her a few times Friday evening, got no responses, and left some voicemails. I was becoming a nervous wreck. Worrying about her, wondering if she left me.
Saturday morning, I finally received a phone call from Jess. My heart leaped for joy, knowing that at least you remembered me.
"Hey beautiful," I answer the phone. But when Jess replied, there was no warmth in her voice
"Matt, hi. Um, I know I've been distant this week,
but everything with my dad," her voice was shaking. She was having a hard time composing herself.
"I just got a lot going on right now. And, and, I just need a break. I'm so sorry, Matt." The call had ended.
Instantly I called back with no response. I called, and I called, each time going to voicemail. I sent several texts and there was no response, not knowing what I did wrong. But I just knew it was my fault. Then I broke down, collapsing to the floor in a sobbing heap.
___________________
A month had passed. A month of depression, of loneliness. A month with no answers. I left text after text, seeing that they were left unread. All phone calls instantly went to voicemail. She had blocked me. I wrote several handwritten letters to her with no response. Sent flowers every other day. I drove to her house but didn't dare to go to the door. It just felt wrong, bombarding her at her house after she trusted me with her address.
Trust went both ways. As heartbroken as I was, I couldn't help but be angry as well. I had tried to cater to her. Made myself vulnerable and yes it was a struggle for me, but I didn't deserve this.
I was just as mad at her as I was at myself. She was straightforward and told me exactly what she wanted. She didn't speak in riddles and didn't play any games. Did she ask a lot of me? Yes. And did I do what she asked? Yes, but not with all my heart as she wanted. I vowed to myself, that if I got another chance, I wouldn't waste it this time. I'll cherish her and everything about her.
My house was a wreck from all the drinking I had been doing. I was not coping well. One drunk night, I saw just how rough I looked in the mirror. I hated what I saw. At that moment, I cast away all my anger and doubts. I vowed to get Jess back and be the best fucking sub in the world.
__________________