Teddy and Kitten: The Long Weekend [MF] [M37+F23] [long] [cheating] [kink]

*This time I let Teddy do the talking, since a few of you asked about his perspective on our affair. I didn’t give him any prompting besides, “Write about the LW, as much as you can remember.” I think he did a smashing job. I’ve added a few comments on the things he’s forgotten due to time or drunkenness.*

Hello. To my pleasant shock, my girlfriend (we gave each other nicknames so hereinafter she’ll be “Kitten” or “K”), revealed to me that she chronicled our first date in a story on a Web site she enjoys. That is both humbling and flattering in a way that’s hard to describe. Sadly, she also told me that she wrote about another date of ours preceding an international trip I took that was not as well-received because as she may have mentioned, I’m married. K suggested that you may enjoy hearing about one of our dates from my perspective and in my voice, so I’ve chosen to do that, which she has agreed to submit on my behalf.

If your intent is to criticize my actions or our mutual decision to be together in the way we are, please spend your valuable time elsewhere. Kitten and I regularly struggle with the difficulty of the nature of our relationship. Judgment by random people on the Internet of a relationship in which they are not involved and about two people they do not know, means absolutely nothing to me and serves no function. If that’s your goal, please don’t bother. I’m writing this as a fun, sexy exercise for my enjoyment and perhaps yours.

A bit about me: I’m a white-collar professional in my late 30s. I try to stay fit for a man my age with a busy life (Kitten loves my chest and says I have the better tits between us, at a firm B cup). I have thinning brown hair, hazel eyes, and a thicket on my chest. I grew a full beard a few months ago, but not so bushy that it looks unprofessional with a business suit. I’ve got an 11-inch dick that’s reminiscent of a novelty baseball bat. Just kidding, it’s probably very average. I won’t say much about Kitten out of respect for her privacy, but she’s an early 20-something college student with a gorgeous mane of blonde hair, curvy in wonderful places, large breasts, and eyes that bring me to my knees. We met on a now-defunct anonymous chat app that I was on out of boredom, hit it off, became more than friends, and talk every day via Snap Chat (which I keep hidden and locked on my phone for obvious reasons).

One of the many things I value about Kitten is her ability to see things about me that I either don’t or won’t, and her willingness to explore things about my sexuality that I’ve never considered. My sex life at home is very by the book and unadventurous; K and I share an innate physical and psychological connection and a mutual insatiability to push our own and each others’ boundaries. Although I’m respected in a high powered and somewhat visible job and usually tend to be dominant in bed as part of my usual demeanor, she’s the only person who’s made me realize that there’s a part of me that occasionally needs to let go of the control I usually hold and submit to her. It’s been a real trip, to be honest.

The weekend after I returned home from my most recent international trip, my wife needed to travel out of town again. Not having seen each other in nearly a month, Kitten and I were ecstatic to be able to see each other and be together intimately. I rented a room for the weekend that included a kitchen because I was excited to taste K’s homemade cooking since her dorm room does not have a kitchen and my home is off limits. The initial plan was to meet Friday afternoon after I left the office, check into the room, then meet up after a commitment she had that evening, get dinner, do a little bit of bar hopping, then head back to the room. Before we met up, I packed some nylon rope and a blindfold and told her to pack the Hitachi wand I’d bought her but we’d not yet used.

Unfortunately, her commitment ran far longer than expected, so by the time we finally met up at the first bar, it was nearly 11:30 at night and I hadn’t eaten. We grabbed a bite and a several drinks and noticed the late-20s group at the next table eyeing us disapprovingly. Funny – one of the things that turn us on the most is seeing how people react to our wide age gap. K, in her very special way, suggested loudly enough for the next table to hear, “Hey, want to go drink in bed together?” Cue additional confused and disapproving glances. We left and realized that the liquor stores were closed – good thing Kitten had a half bottle of whiskey at her dorm, so we made a pit stop. In the many years since I’ve been a student, I forgot that what passes for acceptable booze in college is not exactly the stuff I collect and keep at my home bar.

*Read: Evan Williams. It is such shit and I don’t know why I’d gotten it, other than the fact that I was probably already drunk when I bought it at the liquor store.*

Needless to say, it’s what we had. We returned to the rented apartment and proceeded to drink the half bottle mixed with ginger ale we thankfully were able to buy before the stores closed. A bit later, far drunker than we expected to be, we started making out on the couch. Making out turned to petting, which turned to clothes asunder and us engaging in foreplay on a very small couch. My memory fades a bit as to precisely when, but we wound up in the bed.

I laid her on her stomach and spanked her. “Count them.” “One …” “Good girl.” “Two …”

“Do you know how many you’re going to get? Our age difference.” By the fifteenth, her voice was quivering, her ass was bright red with my handprints and her eyes begged for more of me.

I turned her to her back, spread her thighs with my knees, pinned her wrists above her head with one hand and choked her with increasing intensity with the other. Looking down at her, the moonlight squinted through the blinds and glistened off of her gorgeous milky white skin, the sounds of the street just outside the half-open ground floor window mixing with her purrs and my growls. Never breaking eye contact, I teased her slit with my erection for about five minutes until she begged me to penetrate her. Even when I did, my intent was to make it as excruciatingly slow as possible until I was ready to fuck her the way she liked it. Or so I thought.

I angled my pelvis so that the top side of my shaft dragged along her clitoris so she could feel every inch of it until the ridge of my head grazed it before slipping away and back inside of her. It’s an angle that doesn’t get too deep inside of her and doesn’t provide a ton of sensation for me, but the goal is constant and lingering contact with her clit. I anticipated that this would be a good way to warm her up before I fucked her silly, but I began to notice that she was REALLY into it. I’m a fairly smart guy and I know better than to stop doing something my partner’s enjoying even if I want to move onto something else.

I kept going until I saw her mouth open, her eyes shut, her breath catch, and her body spasm in an amazing orgasm, her moans filling my ears and her release filling my heart. Kitten had confided in me on maybe our second date that it was extremely difficult for her to orgasm from other people, that many had tried, and basically, not to get my hopes up by “trying and failing” to make her cum. I’m beyond that part of my immaturity to take it as a challenge, so the fact that she was able to trust me, relax with me, and that I was able to help her achieve climax made me feel like the most amazing and most powerful, man alive.

Now I knew how to make her cum, so I made it my mission to exhaust her physically and emotionally. I gave her six that night. Apparently I’m unusual in the sense that even after I cum (which I did, twice that evening deep inside of her), I don’t go flaccid for a very long time.

We crashed around 5:00 in the morning and awoke at 11 the next day, hungover to hell. I can’t speak for others, but I’m the most horny when I’m hung over. I reached over and started playing with her nipples and kissing her neck to wake her. Half asleep, I turned her to her back and laid on top of her, brushing her hair with my hand and pressing my erection against her pussy. I pushed inside and fucked her slowly, feeling her get increasingly wet. I came pretty quickly, and knowing she liked the idea of being woken up by sex, kept fucking her and kissing her until she came. And again. And three more times after that, from the same position, her orgasmic moans becoming increasingly louder and more insistent. The fact that we could hear people talking outside the window on the sidewalk made it even sexier that they could undoubtedly hear us fucking.

By this point it was almost 3 PM so we decided to be somewhat responsible, got up, showered, went to the store, bought groceries, came back to the apartment and she made a wonderful, delicious dinner. We digested and went back to bed to nap. Around 7 PM, we woke up again and I decided that I was going to give her as many orgasms as our age difference.

By her fifteenth orgasm over two days, I thought she’d be worn out. I was certainly pretty spent, but she stood up, legs wobbly, and told me to stay put. I stayed as told for a good ten minutes while she went to the other room. When she walked in, she was in a peach piece of lingerie and holding the rope.

“Stand here.” I did as I was told, my mind moving to that hidden, repressed submissive place, as I watched and felt her tie knots over my chest, my back, and my shoulders as I stood naked with the cold fall air seeping into my skin. I’d never allowed anyone to do anything like this to me before and it was exhilarating and nerve wracking at the same time.

*I took my time putting him into a harness. It was gorgeously soft and slippery rope that I let slip between his cheeks and over his still erect cock, each time making him flinch just a little. He kept his head hung, eyes lowered, slowly beginning the telltale descent into subspace that I knew so well from personal experience.*

“Get on the bed. All fours. Put the blindfold on.” I did as instructed. I felt her get behind me and her fingers teasing my exposed ass. And then I felt her mouth. On my ass. I was not expecting this; this is something I guess people do now? Regardless, it felt amazing.

Then I felt the lube. On my asshole. And pressure. “Are you okay with this?” “I trust you .. I trust you.” One at a time, each of her ten fingers entered my ass. Blind to the world with my face in a pillow, I was shaking, wondering what else to expect. And then came something much thicker. I kept moaning, “What is it? Tell me what it is!” No response; I took whatever my girlfriend was putting in my ass. When she was though with me, she un-blindfolded me, rolled me over and held her pet until I stopped shaking. It had been her two fingers. We crashed, holding each other and woke the next morning.

*I get off on the sounds my partners make, and to hear this man moaning and mumbling incoherently into the pillow was an absolute aphrodisiac. I was soaking wet and shaking by the time I was finished with him. Much to his surprise, I’m not as experienced as a Domme as I’d like, and I was drained from just fingering him and spanking his absolutely perfect ass.*

I knew our weekend together would be ending soon, and I needed to bond with her again. I needed her to know the very special way she made me feel. I got on all fours, looked pleadingly at her and begged for her hands again. I love seeing the dominant look in her eyes when she knows she can make this much older man submit to her, and I wanted my best to please her. After she was done, we cuddled again and we switched one last time. I told her, “lay here. Hands above your head. Don’t you move.” I went to get the Hitachi wand. I returned, and told her to spread her legs.

*Now before we get to me and The Wand, I have to expand a little on his second offering of submission. We repeated the experience from the night before, but this time he didn’t need the rope to secure him. He offered himself so willingly, ass raised, awaiting both loving attention and punishment for his wanton begging. This time, however, I got a little more into it. For a while, I’d been contemplating pegging him, to truly mount him and make him mine – and that morning I decided to see how he’d like the rhythm and sensation against his ass. I started to move my hips against his ass, as I gently pumped my fingers in and out of him. Before I knew it, I noticed my own juices running down my thighs and I started fingering myself along with him. He moaned louder and louder and I asked him if he wanted more. He weakly cried out that he couldn’t take it – however, that is not our safeword. As I continued working my fingers inside of him he yelped, begging to know why I wasn’t letting up. Between my own choppy breaths I told him, as firmly as I could, that he was MY pet, MY toy, and MINE to use as I see fit. He collapsed further into the bed and I knew I had done my job. Now, back to The Wand.*

I held the wand in both hands and nestled it against her clit. Turning it on the low setting, she bucked and groaned like nothing I’d seen from her before. I held it there for about 45 seconds and, without warning her, flipped it on the higher setting. She screamed and came and shook; I removed the wand and kissed and held her. “You know what? You’re getting 20 this weekend.” Once more, my good little girl laid there and took another round of the low/high. Panting and covered in sweat, her eyes knew her pussy was throbbing with oversensitivity but I needed her to trust me with giving her more than she thought she could handle. I bore down again with the wand, and her body reacted.

The sounds she made were otherworldly and her body jerked as if there was a current of electricity running through it. These weren’t sensual undulations, they were like she was absolutely possessed. I kept the wand on the highest setting until she screamed and pleaded our safe word after she’d cum twice more. She described the whole experience later as “as if I was on fire.” The power I felt over her body was unlike any dominant satisfaction I’ve ever had. She was sexier than I’ve ever seen.

*I will admit here that we both failed to communicate properly. I had forgotten what subdrop feels like, and I had thought that I was just becoming depressed that the perfect weekend was coming to an end. I was sobbing on the couch before we left the apartment, babbling about how it wasn’t fair but I was just a selfish idiot girl who wanted the world from her illicit lover. He held me tightly but insisted upon getting up and out, knowing that he had to call his wife from his house phone or it would raise suspicion. I spent the rest of the day in my twin-xl bed, unable to stop trembling. Don’t worry, we talked it all through once I realized what had actually happened, and after subsequent Wand sessions, it hasn’t happened again. Add that to the list of reasons I’m so in love with him: he tries harder than anyone else I’ve been with to be the best partner he can be.*

We held each other, got dressed, and I dropped her off at her dorm and I went home to shower and pick up my wife from the airport. It was the most amazing sex I’ve ever had, and things only get better with Kitten. She’s my special, wonderful little princess and I can’t wait until the next time we get copious private time in a hotel in a few weeks, and then again in January. Maybe I’ll write about those, too.

Thanks for reading.

Source: reddit.com/r/gonewildstories/comments/7hj51z/teddy_and_kitten_the_long_weekend_mf_m37f23_long