In my previous story I mentioned how I had an itch inside me which did not need to be scratched, but *wanted* to be scratched badly. However, my path to BDSM was not a straight line. First, I figured if I were to do anything anal again I’d want it to be with a woman. Second, I was apprehensive about looking for older men I didn’t know to scratch that itch. So, the best option I could find was finding a woman to peg me.
My search started by finding **MANY** Femdom personals. All of which required payment, and all of which seemed like a business transaction. No connection. No heart. This was *not* what I was looking for. With this I took the plunge, made an email specifically for this able to be nuked if this didn’t work out, and made a personals ad on CraigsList, way back when it was easy to do this.
The ad was pretty straightforward: “22 M Curious about being pegged”, and in it I laid out my preferences and limits. Essentially I was looking for someone 40 and under, who could host, and was comfortable with a first timer and not jumping into things. I did specify I wasn’t looking to pay for anything as well. Hitting “Post” made me realize I was holding my breath, and was far more nervous than I fully understood.
I waited a few minutes to see if anyone responded, but nothing happened. So, I played a video game for a couple of hours and went back to check it. While I did get a lot of responses to this, a lot of them were spam, older men, or Dommes looking for me to pay them. Yet, a handful were within what I was looking for, and a few were just outside of it.
I responded to the handful to better vet them out. And a couple of those just outside of it as they seemed sincere. I went to work, came home, and went to sleep. Too tired to check for responses. Besides it was only Tuesday. The next day I checked it out and only a few of the women responded.
First was Samantha. 44, 5’7″, skinny but fit brunette, and looking for a young man to train to join her and her husband. After a couple of emails it was clear we didn’t want the same thing. She wanted to train me to be her sub. Mainly so her husband had an asshole to fuck that wasn’t hers. Not what I was looking for, and we parted ways.
Second was Jennifer. 37, 5’3″, curvy petite dirty blonde, and recently divorced. We talked over email for about a week. She was fun, funny, kind, but in the end didn’t connect on what we wanted. Mainly because she wanted to cane me before pegging me, and that did not sound enjoyable.
Lastly there was Emily. 36, 5’5″, curvy busty pawg, and a long haired snow white type. At first the exchanges were a bit cold. Just getting information about each other and feeling the other out. Like two chess players playing for the first time. Yet once the ice broke we got along great! Emily had been divorced for about 5 years and in that time was rediscovering herself. She had a few FWB who were women which is what got her interested in strap-ons. It wasn’t a leap for her to imagine pegging a guy. Yet her, just like me, was having difficulty finding a good partner. After a couple of days of emailing, which turned to texting, we agreed to meet for coffee around 11am that Saturday. Maybe more if we hit it off.
I beat her to the coffee shop a little before 11am, found a quiet table where we wouldn’t be overheard easily, and texted her I was there. She showed up about 5-10 min later, told me to hold the table, asked me what I wanted to drink, ordered and a few minutes later we finally met face to face.
She was a punk/goth wonder in my eyes. Low cut black top, black jeans, slightly flowing and curly jet black hair, and black boots. Later she told me I was the clean cut skinny gamer boy she’d been looking for. Without knowing that, but recognizing the spark in her eyes, we sat down and got to talking. It was more of a date than anything else. We didn’t even discuss the main reason we were there. Emily was the one who realized we had been talking for a few hours and asked if I wanted to continue this back at her place. I had to pause to not agree too quickly and show my eagerness.
She texted me her address, and told me to follow her there. When we got to my car she pulled me in, wrapped her arms around my waist, and kissed me. I wasn’t used to women being this forward (at least not yet) and once my surprise wore off returned her embrace and kiss. I had to try to keep myself under control while I followed her back to her place. Difficult to do with a full nights sleep, coffee, and adrenaline.
The drive took about 20 – 30 min from the coffee shop. I actually lived closer to her than the shop. We parked, got out, did the new but awkward smile at each other, and I followed her to her door and inside her house. Emily had downsized to a 2 bed 2 bath after the divorce, but to me still living at home, it was impressive. Shoes came off, couch was sat on, and a couple of stiff drinks were poured before we started talking again.
After about 10 min of not-so-small talk she shattered what was left of the ice. “So, why do you want to get fucked in the ass by an older woman?” The smile on her face while she sipped her drink was sinister and adorable. After a few deep breathes and a long drink I just told her the truth. About how I had an older man FWB for the last ~8 months, learned some things about myself, and with extreme vulnerability told her I missed getting fucked by someone I could trust and got along with.
Emily couldn’t hide her blushing and lust. Giggled about it, and then thanked me for trusting her. She then told me about how she came to enjoy using her strap-on after her divorce. She had a younger friend who one night soon after her divorce was final while they were drinking kissed her. Kissing lead to many things, and a few short weeks later she was fucking her new lover with a strap-on. That was 4 years ago for her, they were still FWB but didn’t meet up as often, and life was happening to them both. Which was why I was there.
Before I could speak she got up and went to a bookshelf. “I have an idea.” She sat back down with a deck of cards. “It is obvious we both have questions we’d like to ask each other, and I’m pretty sure we both want to move things forward. Let’s play ‘High Card’ and if you win you get to ask a question the other **must** answer truthfully. You can either answer the question asked or remove a piece of clothing, but once you’re naked you **must** answer the question. No more avoiding. Interested?”
I figured she could tell we were both nervous and would both like an excuse to be brutally honest with each other. With that we played until we either ran out of clothes or ran out of questions. I was naked while she still had her underwear on. After that her questions about my time with a man became unavoidable. I could tell she was enjoying herself, and could smell it a bit. She knew I was as I was rock hard since getting naked.
Once the game came to its organic conclusion she picked up the cards, put them back in their pack, placed them on the table, and then quickly leaned over me and kissed me again. Soon we were making out on the couch. She lustfully whispered to me during, “There are so many things I want to do to you… with you…”. Then she broke the kiss, looked me in the eyes, and asked “You want to see my strap and other toys?” through the biggest smile I’ve seen on her. I stuttered a bit finding my voice, “Y-yes.” She got up, grabbed my hand, and started to walk. “Come on!” and she lead me into her bedroom.
Emily had me sit on the end of her bed while she opened up the bottom drawer of her dresser. It was full of toys. She pulled out her strap, in its harness, and put it on top of the dresser. It was about 7″, thick, and a clearish blue. She then started pulling her other toys out one by one putting them back once shown. Emily had rope, a blindfold, a few gags, plugs, a chastity cage (which she put on top of the dresser), glass toys, steel toys, nipple clamps, dildos, vibrators, and a Hitachi wand. Once she put it back she stood up, put her hands on her hips, and told me “If you want to come back after this we can use whatever toys you like.” ending with a giggle.
She then grabbed her strap and walked closer to me. “Would this be too big? I can use a smaller one if you want.” It was big, but not too big so I told her it was fine. Which put a really big smile on her face. She then put the harness on while I watched. While adjusting it and getting the harness just right she asked me some questions. “Do you want to be on your back or doggie style?” I was indifferent, so she chose on my back. “Gentle or rough?” I answered lets start with gentle and go from there. “Do you mind if I talk dirty to you while I peg you?” The answer was no, but I told her if I didn’t like it I’d speak up.
Emily smiled, told me to stand up, and came back with some gloves, lube, and a towel. Draping the towel on the bed she told me to lie back on top of it and spread my legs. I did and felt exposed and vulnerable, but in a good way. She got on the bed between my legs, her strap bobbing up and down a bit, placed the lube to my left, put on her gloves and asked, “You ready?” I nodded yes back.
“Shit, one sec.” She got up, grabbed a couple of pillows, and had me get up. She placed the pillows on the bed and told me to lie down with my lower back on them. It was a bit odd, but told me while lying back down she needed my ass raised a bit. Once in position she poured lube on her gloved hands. She put her hands on my semi-hard cock and lubed it and my balls up. “Damn, these are heavy. When was the last time you came?” I blushed while getting harder, her stroking gently the whole time, and told her through a shaky breath “about a week or so”. Through a rasped hushed tone she told me, “That’s a good boy. Saving yourself like that.”
We locked eyes for a moment and then I felt her finger push and go all the way inside my ass. I let out a yelp, embarrassed, and realized I couldn’t hide. While adding more lube and fingering me she said, “Oh that was adorable! I loved it!” Then while finger fucking my ass, “I can’t wait to hear you make more noises.” Emily was a pro at putting me in my place and lubing me up properly. I learned a lot. Soon a condom came out, Emily thrust forward on her knees, she put it on her strap, and stroked it while she lubed it up. “You ready?” It wasn’t really a question as she leaned over me and put the tip against my ass.
I watched her as she pushed her ‘cock’ into me. She alternated her view from looking at me and looking at what she was doing. Soon she was inside me. She put her hands under my legs, lifted them up, and slowly pushed my ankles as close to my ears they could go. Then she pushed the rest inside me. I moaned, groaned, and let out a few gasps. Placing my legs on her shoulders she leaned over me, kissed my cheeks, and looked me in the eyes. “Tell me… where is my cock?” Emily giggled a bit teasing me knowing men said that a lot. I sighed in lust and told her, “Its in my ass.” She got into a better position to thrust into me, “That’s right. Now be a good girl and make noise for me.”
It was a test. She wanted to use femme names and pronouns for me while she fucked me. I didn’t catch it at first, but honestly didn’t care in the moment. Emily was already pulling herself out of me. Soon she was building up a rhythm fucking me. Her breasts jiggling in her bra, nipples hard through the lace, and her chest rising and falling as she breathed. As she kept fucking me I did as she asked and made noise. I gripped the sheets, moaned, groaned, and more.
Emily kept up the teasing and praise. “Good girl. Let me know how good I make you feel.”, rasping through controlled lustful breathing. Her gloved hand rubbing and stroking my cock and balls. Emily fucked me like this until we were both sweaty and breathing hard. I was getting close, and she noticed. “Beg me to fuck you when you want to cum. Like a good girl. Only good girls get to cum.”
It didn’t take long for me to start begging her. Nearly screaming her name, debasing myself, lost with my only desire to be to cum so the build up would be released. “That’s a good girl. Look at you begging so well! You love getting fucked like a bitch!” I agreed, told her I was going to cum, and she didn’t lose the pace.
Emily pulled my legs up on her shoulders and grabbed my hair pushing my face a bit into my chest. I barely heard her say “Open wide!” through a lustfully sinister giggle. I was too lost in sensation to process what she said until my cock exploded. My eyes closed I gripped the sheets and let out a few hard moans. I felt the first warm splash on my chest. Then another higher up. Then most of it hit my face while she aimed. The last of it dribbling out onto my stomach. Emily let go of my hair and cock, kept my legs in place, gripped her strap against her clit, and kept fucking me. Soon she was moaning and cumming **hard**. I could feel her orgasm shudders through her strap.
As we recovered and I realized I could see out of one eye Emily pulled out of me and put my legs down. “God your ass looks so cute when filled with cock.” she said through a giggle. She crawled over me, her ‘cock’ grazing my thighs. “And you make such a pretty girl when you’re covered in cum.” She brushed my hair back lovingly. “You’d look even better if your make up was destroyed.” Again another giggle. She got up a bit, kissed me on a spot on my forehead that was ‘clean’ and got off of me. “Don’t touch it. I’ll get you a washcloth.”
Emily came back with a warm washcloth and sat down near my hips so she could kneel over me. “God, this is so hot!” She started to wipe up my chest. “Do you mind if I?” With my lips still covered in cum I nodded ‘yes’ having no idea what she wanted to do. Then I felt her fingers, not gloved, move my cum around my face to be over my lips. Then she kissed me, licking up some of my cum, and pressing her tongue through my lips. I returned the kiss, tasted myself, and she shared a loving moment of lust and pleasure.
Once we broke it she licked her lips clean, swallowed, and began cleaning what was left of my cum off my face. There was some genuine praise, kind words, dirty name calling, and more between us until she finished cleaning me off. She stood up, took off her bra and panties, and told me to scoot over a bit. While on top of her covers we cuddled and made sure the other was alright. Talked about the encounter, and kissed some more. After a good long snuggle she got up, got me up, and we took a shower. The sun was about to go down and we agreed it would be best to part ways. I got dressed in my living room while she wore a revealing robe. I told her if she wanted to see me again to just let me know. Even just to hang out. She lead me to the door, kissed me, and said I’ll know she does because she texts me back.
I go to leave, my hand still in hers, and she pulls me back gently. “Text me so I know you got home okay.” We smile and I tell her I will. She kisses me again, and I leave. The ride home was a blissful quiet. I was tired, but not exhausted, and ready for a good meal and a movie before bed. I got some fast food on the way home, and texted her as I parked. I did not get a text back for a few moments. Saddened, but realistic, I grabbed my food and did just as I wanted. I ate, and laid down on my bed watching a movie. I feel asleep during it and woke up the next morning. To no text message.
I returned to my life and pondered if I wanted to put another ad up, or give any of the other women who had messaged after a chance. I decided I’d think about it. Too much at once isn’t good. Most of the time. I went to work on Tuesday and just enjoyed the day for how simple and how content it was. Enjoying another movie my phone vibrates. I flip it open and there is a text from Emily.
> “Are you free for another round this Saturday?”
I smile and put my phone down for about 30 min before texting her back.
> “Yes, I am. When and where?”
I didn’t expect anything, but Emily got back to me quickly.
> “11am at my place. Would you be interested in trying a few things with me?”
I hooked up with Emily a small handful more times before life happened.
Source: reddit.com/r/gonewildstories/comments/swjw3u/mf_first_time_getting_pegged_gfd_femdom_agegap
DMs are open. I’d love to hear some comments/feedback about this or my other story if you have them.