What happens when you have a healthy relationship and one of you wants to try new things?
I got out of the shower, walked to the bedroom, and narcissistically checked myself out in the mirror. A tall guy with an athletic build, dark hair, and piercing blue eyes stared back at me. I may have flexed my biceps and abs. They weren’t quite a six pack, there was definitely definition.
I was just heading towards my closet to get some clothes when a hand slapped my naked ass. “Yes! You know I love that butt!”
Caught off guard, I yelped and jumped a bit. I hadn’t heard my girlfriend, Jen, come into the bedroom. I turned so she could get the other cheek; she’d get annoyed if she couldn’t even them out. Then I turned until I faced her.
Jen was an absolute knockout. She was five-six, her lean face was framed by curly dark hair that hung well past her shoulders. The pajama bottoms and t-shirt hid a thin, athletic build with amazingly perky c-cup breasts.
Her hazel eyes met my blue ones and I wrapped my arms around her torso and pulled her close for a kiss. We made out passionately, our tongues dancing together. I slid my hand under her shirt and tried to remove it altogether.
That’s when her hand gripped my now erect penis. Well, hello sailor!” She broke the kiss and winked at me.
Her other hand grabbed my arm and lowered it down. “Hmmm, no. Not just yet.”
I nodded with a sigh. “You’re right, it’s date night and we have a dinner reservation in half an hour. We should behave.”
She laughed. “Not that, in fact, let’s skip dinner tonight.” She grinned and then led me by her handhold on my dick over to the bed. She pushed me onto the bed and followed me down.
Her lips wrapped around my member and I let out an audible gasp. She blew me for maybe a minute before she stopped, wrapped a hand around the base, and looked me in the eyes. She licked the underside of my tip once while maintaining eye contact. “I want to try something new tonight. Can I?”
I groaned, desperate for her to continue. “If I say yes, will you keep blowing me?”
“God, you’re too easy. Say yes and I’ll get you off as much as you want tonight, when you’re not busy helping me with my…experiment.”
I was intrigued and too horny to argue. “Fuck, yes, keep going and we’ll do whatever you want.”
She smiled and started blowing me again. We’d been dating for eighteen months, and living together for nine of those. Her blowjobs were amazing and, even though I got one almost every day, they always left agog at her skills.
One hand and her mouth worked up and down on my dick, leaving me moaning in pleasure. I felt her other hand sneak towards my ass and I felt a finger enter me.
I gasped at the intruder. Jen had started doing this a couple weeks ago. I’d protested at first but made me promise to try it once. I’d agreed and it had felt so good I told her she could do it whenever she wanted. “That…ugh…isn’t new.” I managed to say between moans.
She paused for a second, my dick popping audibly popping out of her mouth. “No, this is just the warm up.”
Warm up? Whatever, it didn’t matter.
Her finger was pressing on my prostate while she was sucking me. The pleasure was overwhelming and so intense it was almost agony.
She kept up her endeavor for another eight or nine minutes before I felt the too-familiar sensation of a building orgasm. I had hoped I’d last longer, but I was wildly inconsistent: sometimes I’d last for over an hour, sometimes only a tenth of that. The feeling built quickly.
“Jen. I’m close.” She redoubled her efforts pressing hander on my prostate, sucking harder, and jerking faster.
It was too much for me. I cried out loudly as I erupted in her mouth. She sucked and swallowed like a champion, never spilling even a drop of the six shots I unleashed. My hips bucked as she kept sucking.
I got super sensitive after I’d cum, and she’d gotten into the habit of half-torturing me by continuing to blow me nonstop until I’d deflated in her mouth. I gripped the bedspread and whimpered, completely overwhelmed by the sensation.
Eventually, my dick softened and she let it fall from her mouth. She went back for one last suck, and then met my eyes and said “Roll over.”
I did. I had promised after all. I heard a cap snap and a very lubricated finger reentered my ass. I moaned into a pillow and she worked it in and out of me.
After a few minutes, she surprised me by slowly pushing a second finger in. I gasped again but she shushed me and went slower. Eventually, my hole acclimatized to the second finder. Then she repeated the process with a third.
Once I could handle three fingers easily, she pulled them out. “Don’t move, I’ll be right back.”
I felt her leave the bed, I heard walk away and then the bathroom sink ran for a minute or so. I heard her come back into the room.
“Okay, just lie there. I’ll do the work.”
I had a suspicion about what was coming. My guess proved correct when she returned to the bed and I felt something rubbery and lubricated push against my hole. I moaned as the strap-on pushed inside me.
She did it slowly, but eventually the entire thing was inside me. I felt her hips pressed against mine and her breasts against my back.
Once it was inside, she started sliding it back out, just as slowly. It felt incredible and I moaned as she did. When it was almost completely out of me, she reversed course and pushed it back in, just barely faster. She worked it in and out of me again and again, getting incrementally faster each time.
Before I knew it, she was fucking my ass hard and fast and we were both moaning. She grabbed a handful of my hair on the back of my head. “Tell the truth. You’re loving this, aren’t you?”
“Fuck. Yes, Jen. Oh fuck, you can do this to me any fucking time you want.”
I think that was what she wanted to hear, because she started fucking me even harder. “Good, because I’m going to. Now get up. You’re going to ride me.”
She pulled the dildo out of my ass and laid down on the bed. I mounted her the same way she’d done to me countless times, lined the strap-on up properly and slowly lowered myself down.
She bucked her hips up and the entire thing entered me in one movement. I kept lowering myself, forcing her hips down. Then I started riding up and down.
Well, shit. This was amazing. I felt my own dick bouncing up and down and realized I was hard again.
Jen saw it too and barked an order at me. “Keep going! Jack yourself off while you ride me.”
I obeyed and continued what soon proved to be a fairly intense leg workout. We lost track of time as she watched me jerk off as I rode her, but I looked at the clock on the nightstand when I started to get close and realized we’d been at it for more than twenty-five minutes.
“I’m getting close.”
“Good. I want you to cum with my dick in your ass.”
As I was about to cum, I slammed myself down, hilting her strap-on into my ass and pressing it against my prostate as hard as it’d go. Ropes of cum exploded out of my dick and the pressure and distance was astounding.
The first shot hit her cheek, just under her right eye. The second draped over her lips, her open mouth, and onto her chin. The third hit her neck and collarbone. The fourth, her left breast. The fifth, her stomach.
We stayed like that for a few minutes, both of us panting. Finally, I found the energy to speak. “Holy fuck, Jen. That was intense. What brought this about?”
She smiled wickedly at me. “Well, you get to fuck my ass. I thought it’d be hot to turn the tables on you.” She paused for a moment. “I’m glad you enjoyed it, I want to do this all the time.”
I couldn’t think of a reason to say no, not that I wanted one. I just looked at her and realized our relationship was changing, and not in a bad way.
“Don’t get up, but could you clean me up with your tongue?”
Well, that was also new. Eh, whatever. I bent over as much as I could and licked the load off her stomach. I worked my way up cleaning up all five shots and collecting them in my mouth. After I licked her cheek clean, I met her mouth with mine and we shared the load with a passionate kiss. She definitely got most of it, but I wound up swallowing some of it too.
We rolled onto our sides and she eventually pulled the toy out of me. I lay there exhausted and drifted off to sleep.
I woke up early the next morning when Jen started sucking me off. She did that a lot. In fact, the only times she didn’t wake me up that way was when I woke up. On those days, it was her turn to wake up with my tongue licking her snatch. After a few minutes of enjoying the absolute heaven that is her mouth, I pulled her off me, flipped her onto her back, and we fucked like animals for over an hour until I started to get close. Despite her having an IUD, she always preferred I came anywhere other than inside her pussy. It had been pretty early on that we’d fallen into the routine of me pulling out when I got close and her having me cum in her mouth.
It was Saturday and we spent the day relaxing around the apartment and smoking some joints. We’d agreed a long time ago that pot was only something for when we didn’t have work the next day. Apparently we were both in the mood to get wrecked because we went through a huge portion of our stash, lots of joints and a pair of edibles apiece. We’d have to go back to the dispensary some time in the near future.
I lost track of time. I vaguely remembered us eating lunch and then Jen having me lie on my back while she fucked my ass again with the strap on.
I came partially back into focus in the early evening. I was lying on the couch and Jen was sucking my dick again. I kind of remembered eating her out through three or four orgasms. She’d returned the favor by blowing me, but she’d never stopped. I had a distinct memory of looking at the clock right before I came. It was half an hour later and she was still sucking my dick. I wasn’t sure if she realized I’d been soft for most of that time but I wasn’t going to stop her. It felt absolutely incredible. She kept going and something happened that I never knew was possible. I came while I wasn’t hard and without shooting a load.
Holy fuck. The dry orgasm was intense and lasted forever. Jen never stopped blowing me. Eventually, a little while after it ended, she seemed to come to her senses and pulled my dick from her mouth.
“Oh, I got lost in thought. How long was I doing that?”
“An hour, maybe an hour and a half?”
“No wonder my jaw is sore.” We looked at each other and burst out laughing. We partook a bit more and had a few drinks while we cuddled on the couch.
“Hey, let’s try something new.” Jen led me by the hand into the bedroom. She placed me at the foot of our double bed, facing it. “Stay there and don’t move.”
I was too dazed to even think about disobeying her. After a minute or so, I felt something around my ankle, then the other ankle. I looked down and Jen was securing a strap around my left ankle. Attached to the strap was a long pole that, in turn, was attached to the strap around my right ankle. The whole ensemble forced my legs apart.
“Right, get on the bed. Hands and knees. I crawled up onto the bed. After a minute or so I felt something metallic around my right wrist and then my left. I’d used the handcuffs on Jen more than once and she’d done the same to me. Our bed was one of those Ikea numbers that had a headboard made of a bunch of different wooden rods. Jen took a second pair of handcuffs and cuffed the chain of the first pair on one end. She cuffed the first pair of cuffs to the headboard’s vertical pole.
Ah, this maneuver. I’d come up with it to use on her. Each cuff end could rotate easily. With this setup you could cuff someone to the headboard but still be able to flip them over without issue.
I’d barely gotten settled when I felt Jen push the strap-on into my ass. She’d used it enough on me since the night before that it met little resistance. She wasted no time and started pegging me again. I moaned and she fucked me doggy style for half an hour before she collapsed onto me and we both fell onto the bed. We lay like that for a while, breathing together.
“Tommy, I know it’s weird timing, but can I ask for a favor?”
“Of course, sweetie. What’s up?”
“Okay, I told one of my friends how awesome it’s been fucking your ass. She got pretty envious. Could we invite her over to have a turn with you? I really wanna watch that. You can even fuck her after.”
Jen and I had had threesomes before with one or two of her friends. The key was a mutual understanding that everything during those times was in good fun and didn’t change our emotional devotion to each other.
After the crazy blowjob she’d given me earlier, I wasn’t sure if I’d be able to go again. But it wasn’t always about me. Relationships are a two-way street, even when a three-way is involved.
“Oh, uh sure. When were you thinking?”
“I’ll text her now.”
“Okay. I guess you’d better uncuff me.”
“Nope. Stay just like that!”
Oh boy. I’m pretty sure I’d be getting embarrassed if I were less stoned. Wherever, we had fun pushing each other’s boundaries, it was my turn.
Jen put another joint to my lips. “Here, puff on that while we wait for her to get here.”
It wasn’t the easiest thing to do, but I managed. I had just barely finished the entire thing when I heard a knock on the door. Jen slipped a sleeping blindfold we sometimes used over my eyes.
“We’ll be right back, don’t go anywhere.”
I rolled my eyes, not that anyone could see. I heard some whispers and a little giggling and I felt my face blush. Then I felt the strap-on push into me and I moaned.
The toy buried itself in me and I felt someone press into me. “Hey sweetie, she wants to watch first so I’m going again. Then it’s Lexi’s turn.”
Jen fucked me for five minutes or so before she pulled out. I heard her say “Oh fuck, I’m going to cum playing with myself while I watch this.”
A throaty, feminine voice I didn’t recognize said “Thanks, Jen.” And then I felt more pressure on my hole. I guess Jen’s friend brought her own toy because this one wasn’t as wide as before. But it still felt fantastic.
I moaned as it slid into me. I felt a slender figure lean against me, her breasts pressing into my back. Lips kissed the back of my neck and I felt her chew gently on my earlobe. A hand reached around and grabbed my dick which, to my surprise, was hard again. A very feminine voice whispered in my ear. “I’m going to take my time fucking your beautiful ass. If you haven’t cum by then, I’ll let you put your dick in whichever one of my holes you want.”
With that, our mystery girl started fucking me at a steady pace. She had a vicegrip on my dick but wasn’t really jerking it at all. I moaned over and over as five minutes turned to ten which turned to fifteen and then twenty. I only managed to hold the classic doggy position for the first five or ten minutes, after that the exhaustion, the alcohol, and the pot overwhelmed me and I felt my shoulders fall onto the bed, my face pressed into the mattress.
Unexpectedly, I had two dry orgasms as she fucked my ass. I was in heaven and I never wanted this to stop. From the sound of Jen’s moaning and running commentary of “Yes, fuck his ass. God damn. That’s so hot,” she’d had at least four.
A little after the thirty minute mark, I had a third dry orgasm. I was on the tail end and still moaning enthusiastically into my pillow when the girl in my ass said “Oh fuck, I’m gonna cum.”
She pushed all the way into me. To my confusion, I felt something warm and wet splash inside me. It took me a minute to work out what was going on.
Oh.
Eh, whatever. A girl is a girl, I decided. It doesn't matter if she was cis or trans. Besides, she’d just given me thirty minutes of absolute ecstasy and I trusted Jen to make sure her friend was clean.
Still. Jen hadn’t specified I’d be getting fucked with a real dick instead of a toy. I was going to have to do something to get even.
I moaned again and Lexi held me there for another couple minutes before she softened and pulled out. While she was still hilted in me, Jen removed the blindfold.
Without missing a beat, I said “Jen, you didn’t tell me my ass was going to get fucked by a real dick.”
She blushed. “I knew you’d love it, but I was afraid you’d say no.”
I looked at her. “I absolutely did love it. But be honest with me next time, okay?”
“Okay, how can I make it up to you?”
“Funny you should ask. There seems to be a lot of cum in my ass. Be a dear and clean it all out.”
To her credit, Jen didn’t even complain. She spent the next ten minutes giving me a rim job, licking the cum out of my ass.
Right after she’d started, I looked at Lexi. She was gorgeous: a little taller than Jen, an amazing figure, great breasts, platinum blonde hair. “Go clean yourself up. Once I’m untied, we’ve got more fun on the docket.”
Ten minutes and a fantastic rimjob later, Jen uncuffed me and freed my ankles. I wasn’t really angry with her, but I was definitely about to extract some payback.
I had Lexi lay on the bed. “Sweetie, blow our guest until she’s hard again.”
Jen obeyed and, before long, Lexi had an erection to match my own. Well, almost. Her’s was a bit narrower and maybe only six inches long, half an inch shorter than my own.
I cuffed Jen to the bed, exactly as I’d been. I turned to Lexi. “Just checking. Do you like fucking girls too, or just guys?”
She smiled at me. “I’m pan. What were you thinking?”
“Well, I think my wonderful girlfriend deserved a turn getting her ass fucked, don’t you? While you’re at it, I’m going to give her a good face fucking.”
As payback went, this barely qualified. I knew Jen had always wanted to take two dicks at once. The look of absolute lust on her face confirmed what I’d suspected, she was going to enjoy this.
I knelt in front of Jen’s face as Lexi warmed up her ass. My dick had been in her mouth for barely five minutes when I watched Lexi push her own member into my girlfriend’s ass.
Jen moaned into my dick as Lexi entered her. Then Lexi and I got to work.
We fucked Jen hard and fast from both ends nonstop. After a minute or two, she both leaned forward and started making out. It disrupted our rhythm a bit but we quickly got the hang of it.
We fucked her like that for twenty minutes in perfect sync. She spasmed a few times as she came but we ignored her and just kept fucking. Without coordinating, we both hilted out dicks inside Jen at the same time and came. I could tell because her breathing got as frantic as mine as we kissed. We held it like that for a minute or two before I broke it off and pulled my dick out of Jen’s mouth and got off the bed.
Jen gasped for air. Lexi pulled out of Jen’s ass and I replaced Lexi’s genuine article with Jen’s silicone facsimile. Jen moaned as I pushed the toy as deep in her ass as it’d go. Then I picked up Jen’s body and flipped her onto her back. I covered her eyes with the blindfold and turned to Lexi. “Want to go smoke on the balcony?”
She smiled at me and agreed.
“Great, go get cleaned up…again. It isn’t even nine yet. We can smoke for a bit while I decide which one of your holes I get to play with.”
The apartment’s balcony isn’t much. Maybe four feet deep and eight feet wide. It had a sliding glass door that led to the living room. Jen and I kept a pair of lawn chairs for when we wanted to sit out there and watch the city lights. At twelve stories up, we didn’t have to worry about anyone catching us on the occasions I bent her over the railing and railed her.
Lexi met me outside a couple minutes later. I passed her a beer and my lit joint.
We sat in amicable silence for a bit, passing the joint back and forth, before she said. “I’m sorry she didn’t tell you I was trans in advance.”
“Eh, don’t worry about it. She didn’t technically lie. She just left out what…kind of equipment…you’d be using.”
She gave me a searching look. “You really don’t care if I'm trans?”
I shrugged. “I’m uncomfortable around guys, around masculine…energy. Always have been. And they’ve never done anything for me aesthetically. It’s why Jen and I have never invited another guy into the bedroom. I couldn’t get it up with a guy around if I tried. This was very different, otherwise I’d never have been able to doubleteam Jen with you. You’re gorgeous and, as soon as I’m ready, I’m going to give you a good fucking.”
Lexi looked at me. Tension had visibly drained from her. She laughed. “A good fucking? Who talks like that?”
I returned the look. “I am incredibly stoned right now.”
Lexi hogged the rest of the joint to herself, which was probably for the best. When she finished, I said “Wanna help get me back up?”
She got out of the chair and kneeled in front of me. She took my dick in her mouth and started sucking. It took about a minute of watching this beautiful girl’s head bob up and down before I was hard again.
She blew me for another minute or two before she turned around and leaned forward on her elbows. I noticed she had a butt plug in her ass.
I carefully removed the toy and slid my erect penis into her ass. We moaned at the same time. It was slow going at first, but eventually I was fucking her at a solid pace. She moaned and a flurry of profanity and verbal reinforcement left her mouth. “Fuck. Don’t fucking stop. You feel so good. Yes. Fuck. Yes. Yes, yes yes yes yes. Shit. Fuck my ass. Oh god, it’s sooooooooo gooood.”
I pounded her ass for fifteen minutes before I unloaded inside her. As I pulled out, I noticed she was hard.
“Lexi, lie on your back.”
She looked at me questioningly but did.
I took her dick in my mouth and she gasped.
I’d never sucked a dick before. It was hot and hard but also soft at the same time. I just tried to emulate everything Jen always did for me, aside from fitting the entire thing in my mouth. I only managed to get most of it, I couldn’t get the last couple inches. After maybe ten minutes, Lexi rewarded my efforts with her final orgasm of the evening. She came in my mouth and I did my best to swallow everything.
I got up and helped Lexi off the floor. I led her to the bedroom and we uncuffed Jen. Then we had her lick Lexi’s ass clean of my cum. While she was going down on Lexi’s ass, I hopped in the shower for a quick rinse. I was just wrapping myself in a towel when Jen shambled in and brushed her teeth. I did the same and we headed to the bedroom together. Lexi took yet another brief shower and borrowed one of our toothbrushes before joining us. The three of us were a bit of a tight fit on the bed but we drifted off to sleep cuddled together.