Shelly and I met in junior college. I was taking automotive repair technology classes; she was taking her general education classes. We actually met in the cafeteria during lunch break. The place was full, and I was looking for a table to sit at. Shelly and another girl were at a table with an extra chair, so I asked if I could join them. They were both very pleasant people. I don’t remember the other gal’s name, but Shelly really impressed me, so I would look for her on campus whenever I was changing classes, in the cafeteria, or in the library.
After running into her a few times, I finally felt comfortable asking her out for a date. She accepted my offer, and we met at a local tavern on Friday night. After a couple of beers, I asked if she was hungry, and she was. We left the tavern and walked down the street to an all-night cafe.
After eating and chatting, it was getting late, and I had work on Saturday; I worked at my dad’s automotive repair shop. I was explaining to Shelly that I had to work the next day; she seemed a little disappointed that our date was ending. Picking up on this, I mentioned that I was free on Sunday if she would like to spend the day at the beach. I offered to pick her up since the beach can get crowded and parking might be difficult to find.
I had Shelly in my car at 8:30 on Sunday morning; we wanted to find a good spot on the beach—parking and gathering our stuff, towels, mats. We headed down the beach. When we got to the cliffs, I told her that any further down, we would encounter naked people, mostly men.
She said that was okay, as she didn’t mind looking at swinging dicks. She did ask if we had to get naked also; I answered no, only if we wanted to. We found a great spot, laid out our towels and beach chairs. I dropped my shorts. I had a tight white Speedo on; it accentuated my cock. Also, I knew when it was wet, it would reveal my cock in an almost transparent view.
Shelly had on a skimpy two-piece bikini, also white, which made me think she wanted to expose some skin, possibly tits, maybe even her pussy. It didn’t take long, and we had a small audience. Guys walking by, covertly looking at us, probably her mostly.
We had just gotten out of the water, and these two guys, holding hands, tight Speedos on, set up towels about 30 feet from us. They laid out their towels, stripped off the Speedos, and hugged. They were both nicely hung, not huge, probably 4” flaccid.
I watched Shelly check them out. She took a deep breath when one bent over to adjust his towel, and his balls hung down, long and loose. Shelly lay down on her back and placed her hat over her face. I had a great view of her body; I could see her nipples were hard, a little pink showing through the suit, and couldn’t see anything showing on the bottoms.
We had been there for about 3 hours. I suggested we get some lunch, and Shelly agreed. When we got back to the car, she said, “I’ve got stuff at home; let’s just pick up a bottle or two of wine, and I’ll make lunch.” Perfect, I thought.
Once inside Shelly’s apartment, she turned and hugged me. I wrapped my arms around her upper back; she wrapped hers around my waist. She pulled me in tight. I think she was checking to see if I was hard. Well, I wasn’t until she pulled my groin in tight to hers. I went from flaccid to rock hard in a nanosecond.
When she pulled back, she had a grin on her face. After lunch and a bottle of wine, sitting on her couch, she cuddled up to me, kissed my neck, grabbed my hand and placed it on her right breast, then she reached down and cupped my cock in her hand. Looked me in the eyes and said, “You want to play, Dick?”
We started making out for about 10 to 15 minutes. I had been massaging her tits the entire time, even reached down to rub her pussy. She had been reaching under my clothes, pinching my nipples, and undid the belt and snap on my shorts, rubbing my cock over the Speedo.
That’s when she slid down between my knees, reached up to pull my shorts off, then my Speedo. When the Speedo cleared my cock, it sprang up vertical. With my shorts and Speedo off, she started to lick my cock, cradling my balls in one hand. She licked and sucked each nut into her mouth and lathered them with spit. Took my cock all the way down her throat.
I am average in length and girth, 6” long, 5” around; she had no problem with taking all of me. It felt wonderful. She was a great cock sucker, had me on the edge in no time. I pushed her off before I orgasmed. Reached for her top and slid it down to expose her tits, awesome tits, hard pink nipples, slightly darker aureoles, a nice big handful. I asked her to stand up so I could remove her bottom. As I slid them down, exposing her clean-shaven pussy.
Her pussy was beautiful, already some moisture collecting in the crease. I leaned forward and ran my tongue right up and over her hidden clit. A gasp escaped her lips; she said, “Let’s get more comfortable,” and led me into her bedroom. She lay back in the middle of the bed; I just spread her legs and settled in, licking her pussy.
The gasps, groans, and moans she made were really sexy and excited me a lot. I finally had her lips open and was concentrating on her little nub, coaxing it from its hood. I got up on my knees, working on her clit, when I slipped one, then two fingers inside her. When I touched her G-spot, she let out a loud moan, “Oh my god!”
I licked and rubbed her clit with my tongue, fingered her G-spot, until she was screaming my name, calling to God, begging me not to stop. She finally pushed my head away, grabbed my wrist, and asked me to stop; she needed to catch her breath.
After catching her breath, I moved to sit next to her, hugging her. She dropped to her knees, spread my legs, and moved in. She grasped my cock, licking and then sucked me into her mouth; all the way, I felt her tight throat. With her hand, she circled the base of my cock with two fingers; with her other hand, she grasped my balls, doing the same; two fingers circled the base of my balls. She sucked my cock voraciously, working the head as if her life depended on it.
I could feel my orgasm rising. I started moaning, “I’m going to cum.” I was squirming around, just as my cock expanded, ready to shoot. She clamped her fingers around my cock and squeezed hard; at the same time, she did the same to my balls and pulled them down, stretching them taut. It was almost painful.
My orgasm ruined, I looked at her, asking why. She just started all over again, sucking, taking my cock into her throat, swallowing it, rubbing my balls. As I approached orgasm again, I kept quiet, but my cock gave me away; it expanded, ready to squirt. Fuck me, she did it again. Ruined my orgasm.
This time she just giggled and smiled. When she felt me start to deflate, she went back to sucking, only this time I saw her grab the lube on the table, Vaseline, and dip her fingers in it. She started to rub it all around my bottom, my rosebud. She wasted no time, and she was finger-fucking my ass. When she hit my prostate, I erupted like a fire hose, shooting cum, squirt after squirt, in her mouth. Then I passed out.
When I came to, she still was suckling on me. A big grin came across her face, kissing the tip of my cock. She asked, “How was that?” I was still in shock from the incredible orgasm; I could only nod.
After regaining my senses, I just pulled her up to embrace, hug, and kiss; her mouth tasted like sperm.
After that day, Shelly and I started dating regularly; we became a couple. The oral sex was a regular thing, at least 3 to 4 times a week. She would mix it up when sucking me, sometimes edging me, sometimes fingering my bottom, other times just a quick blow job. She would always swallow my cum, until one day when she just quickly sucked me off, then with her mouth full of my load, she kissed me and pushed the entire load into my mouth. Which I swallowed; this became common for her.
She instructed and trained me on the art of cunnilingus, how she liked my tongue, how hard, how fast, when to use a finger or two, where to put those fingers, and her G-spot. She even showed me when to put a finger in her butt.
We carried on with oral sex for 8 months. I would talk to her about how I wanted to have intercourse with her. I thought about it all the time. I would masturbate thinking about fucking her.
It was the summer between the first and second years of college. I took the summer off, but Shelly took classes all summer. Tragedy struck: my dad had a stroke; he almost died when he fell and cracked his head on a metal table in the shop. He ended up being paralyzed on his right side.
I had to quit college to take over running the shop; at the same time, I moved back home to help Mom when I could. Shelly and I continued to date; the oral sex was less frequent; now it was mostly on the weekends. We would talk on the phone most every night and have phone sex; we would both masturbate to orgasm. I did get to stay and sleep at her house on Saturday and Sunday nights.
I was going crazy thinking about fucking her, when one Saturday night I asked her, “Shelly, when are we going to have sexual intercourse?” She looked at me, smiled, and said, “I thought you would never ask.” That night we had oral sex; she orgasmed, but not me. Then she pushed me onto my back; my cock was like a flagpole. When she just got up over me on her knees, reached behind and grabbed my cock, then just sat down, taking me all the way inside her pussy. The feel of her pussy was to die for; she rode me for at least 5 minutes before I screamed, “I’m going to cum.” Shelly just smiled and said, “Fill me up; cum in me.” Her pussy started squeezing my cock; she was milking the cum from my balls. It was such an intense feeling, nothing like other girls I had fucked; this was just over the top.
She finally just clamped down on my cock, squeezing me. She leaned forward and kissed me, then whispered in my ear, “Dick, I didn’t cum. Will you lick me some more now?” I nodded yes. She just moved up and sat on my face.
I was used to eating my own cum from the kisses after blow jobs; this was different. The musky smell from her pussy from fucking, mixed with the smell of my cum, was intoxicating, plus all the juice—hers and my cum—leaking out. It was definitely messy; she was grinding her pussy all over my face, lips, nose, eyes; she settled down right on my mouth. I wanted to please her, so I dove right in, tongue inside, cum pouring into my mouth. I nibbled on her clit, I tongue-fucked her. She was moaning, gripping and pulling my hair, with a final scream I thought would elicit a call to the police by a neighbor. After Shelly orgasmed, she rolled off me, curling into the fetal position.
She lay there for a good ten minutes before she rolled back over, embraced me, saying we need to do that again, are you hard yet? Then, laughing, she hugged and kissed me, finishing with “I’m serious, Dick, that was awesome.”
This was our life now for the next few years; my dad did recover, although he never worked again. Shelly and I did move in together. She was now enrolled in a master’s program and started working as a lab assistant for a company called XGENX.
The shop was doing great; in fact, I had expanded to 5 techs, a service advisor, and a receptionist. Shelly and I talked about marriage, but decided to wait until she graduated from the master’s program.
Sex with Shelly was always an experience; she wanted to try everything. We would watch porn, then try what we watched. We fucked in every position you can imagine, every hole she has. She even had me tie her to the bed; she bought a Sybian and would ride it until she was exhausted. Shelly was a sexual freak!
One night, we were lying in bed, with the afterglow from fucking, Shelly was fondling my soft cock. She says, “You know, Dick, all of our experimenting has been conventional sex—oral, vaginal, anal. We haven’t done anything really kinky, other than tying me to the bed. I think it’s time we experimented with some different things, with you on the receiving end. Like tying you up, putting things in your butt, dildos, butt plugs, strap-on, have you ride the Sybian. Dress you up in my clothes for a night, play Domme and slave, what do you think?”
Shelly knew I would not refuse her; anything sexual Shelly wanted, Shelly got. So started a new chapter in our sex life. She bought butt plugs, from small to ridiculously large; the same with dildos, a couple of different styles of strap-ons, one that was a harness type that took different dildos, and one that was called a Feeldoe; it fit inside her pussy.
We watched all kinds of videos on how to use all these toys; we even watched some bisexual videos, 3somes, and 4somes, men with men, women with women. I wasn’t sure about having sex with another man, but I promised to keep an open mind.
Shelly experimented on me with butt plugs, from small to bigger; she even got me used to wearing one to work. That was really kinky; I was so horny by the end of the day.
Shelly fucked me with the strap-on; I actually liked the feel the best. My butt hole got used to being fucked, I even started to orgasm when she fucked me, without touching my cock. It was a prostate orgasm; God, I loved those. It was so intense; the cum would just flow out of my hard or soft cock.
Shelly started to wear my shirts and jeans, with her cock sticking out the fly, and tied me bent in half on the bed. Telling me to call her Sam as she fucked my butt. The second time she did that, I orgasmed so hard I passed out.
The time together just flew by. Shelly was graduating with her Master’s degree in pharmaceutical engineering, and she was now in charge of her own group. We were planning our wedding for the next September, which was 6 months away.
The time went quickly; we were now in the Caribbean on our honeymoon, staying at a resort that offered nudist beaches and intimate opportunities, and was couples-only, Shelly’s request. I knew she took a couple of butt plugs and her Feeldoe, plus lots of sexy clothes, and also a new bathing suit for me, a red Speedo that was one size smaller than I usually wear.
The first night there we consummated our marriage; I fucked her, then she fucked me. We met a few other couples, had dinner, and hung out on the clothing-optional beach with one couple; we stayed in our swimwear that time. I struggled not to have an erection; both Shelly and the other couple were in very revealing swimwear. The other guy, Bob, had an erection most of the time; he was also in a Speedo so that nothing could hide it.
Both Shelly and Carol were in very skimpy bikinis, both with just a thin strip up the butt crack and very little covering shaved pussies, small nipple triangles covering their tits.
We went to dinner with them that night, then drinks at the outdoor bar; both ladies were dressed provocatively, very sexy.
The ladies were definitely getting drunk; Bob and I weren’t drunk but close. Shelly suggested we all go back to our suite; I knew where this was headed, as both ladies had been flirting with each other all night.
It didn’t take but about 10 minutes. I had just gotten drinks for everyone when I found the ladies deep in an embrace, making out. I handed Bob his drink, and we sat together to watch the show. Shelly was definitely the aggressor; she took charge of their lovemaking.
It didn’t take long, and they were on the bed, removing each other’s clothes. As soon as the naked bodies appeared, Shelly had Carol on her back, her legs spread wide, and was giving her oral. The two women were soon in a 69 position, going wild on each other, until both had a body-shattering orgasm. Carol left a huge spot of wetness on the bed; Shelly covered Carol’s face in copious amounts of pussy juice.
When they rolled apart, Bob fucked Kelly, and I fucked Carol. That was our first 4some, and it was a doozy! Afterward we sat around naked, talked about how fun that was. I noticed that Bob’s cock was slightly longer than mine, but a lot thicker. And he was flaccid, as I was.
Both Carol and Bob had swung for a long time; both had sex with the same sex. Both were bisexual. They encouraged me to try it, saying if I enjoyed Shelly fucking me, how much better a real cock would feel.
The next morning was warm; Shelly and I stayed in bed. We talked about the previous night, how I would feel about having a same-sex experience. I told her I wasn’t sure I could initiate it, but I wouldn’t refuse it for her. I could tell she was thinking about how to set that up.
Two days later, we were on the nudist beach with Carol and Bob when the subject came up. We all talked about it, and I agreed to have sex with Bob that evening, in their suite.
Talk about being nervous, I was a bundle of nerves, to the point Shelly gave me a Xanax; she also gave me a little blue pill, Viagra, but told me it was to counter any adverse reaction to the Xanax.
When we arrived at their suite, Carol was wearing a red, see-through nightie and looking absolutely stunning. Bob had on an open short-sleeved shirt, showing his masculine, hairy chest. He also had on a pair of short shorts, with his cock producing a prominent bulge. I’m thinking that big thing is going to be inside me tonight; I’m scared of how I will react.
I have taken a dildo that long or longer, but nothing that fat. A few more drinks, I was definitely relaxed, Xanax and alcohol, plus my inability to refuse any suggestions had me right where they wanted me.
When Bob leaned over and kissed me, pushing his tongue into my mouth, I accepted it and kissed him back. When he took my hand and placed it on his cock, I grabbed it, squeezed it, and rubbed it, then I pulled his shorts down so I could feel his flesh. My first touch of a cock that wasn’t mine.
The thrill I felt, I can not describe. Bob then pushed me to my knees, between his legs. He shimmied out of the shorts, held his cock up, and told me to lick it. I licked up and down on his cock, he then held his balls out and told me to lick them. He took my hand and placed his cock in it; I grasped it, squeezed and stroked it. Then I took him into my mouth; it was a stretch, and I could only get about half of him.
All the time I explored and sucked Bob’s cock, he stroked my head, giving encouraging words. Telling me how nice my mouth felt, I started to taste a slightly salty, silky fluid collecting on my tongue; it was his precum. It did taste good. I glanced over at Shelly; she had her finger busy in her cunt and rubbing her clit. Carol was doing the same.
They both mentioned how hot it was to see me with a cock in my mouth. I didn’t know it, but Shelly had been taking pictures of me and Bob’s cock in my mouth. Bob pulled me off his cock and said he almost orgasmed, but held off as he had somewhere else he intended to cum.
Bob then stood up. He came around behind me and told me to stay on my knees but to get my chest up on the couch. I felt the cool lube as he applied some to my rosebud, then he pushed a finger inside me, then two fingers, and finally three fingers. He worked them in and out, stretching my hole, for the main event, fucking me.
I was so relaxed, except my cock was hard and poking into the couch. I felt Bob move back a bit, then I felt the knob of his cock on my hole. He pushed a little; I felt myself open up for him. The stretch burned a little, then he was inside me. Both Shelly and Carol gasped, I guess at how easy I took his cock. Bob then fucked me slow, fast, changing speed and intensity, until he pushed in all the way, held it deep inside me. I felt his cock expand, then some pulses, some heat, his groan, and then he fucked me hard for a few strokes.
Bob relaxed, his cock still in my ass; he told me to squeeze his cock with my sphincter, to get all the cum out. As I’m doing that, I reached down to feel my cock, still hard but leaking; I had not cum yet. Bob then pulled out, pulled me back, and told me to lie on the floor on my back. He proceeded to give me a blow job. I lasted all of 2 minutes, then blew a massive load of cum in his mouth. Bob stood up; he kissed his wife, giving her some of the cum; then he did the same to Shelly.
After the sex with Bob, we all sat around, naked, and talked about it. Did I like it? How was my first real cock? Would I do it again? What did Shelly think about it? Just a sexy conversation about men having sex together.
The honeymoon was coming to an end, two more nights, then a long flight home, and back to work. Shelly had one request still not completed; she wanted to have sex with this big, dark-skinned man we saw on the beach. He wasn’t naked, but you could tell he was hung. She also wanted to have me play the cuck husband role.
Shelly and I were sitting in the outdoor bar when he walked by. Shelly caught his eye; he smiled at her and walked to the beach. He was wearing a black Speedo that accentuated his prominent manhood.
After he was settled in, lying on his towel, Shelly walked down and just sat in the sand next to him and started a conversation. It didn’t take long till they both got up, walking towards me. Shelly says, “Follow us, Dick.” I’m following them up to this man’s room. Once inside, Shelly just goes for it, drops to her knees, pulls his Speedo down, takes his cock in her mouth. The sight of his cock, it wasn’t super long, maybe 8,” but it was thick; Shelly couldn’t get her hand around it.
Shelly sucked him for maybe 5 minutes, then she lay on the bed, spread her legs, and said to me, “Dick, put his cock in my cunt.” Somewhat stunned, I looked up; he just nodded, so I grasped his hard shaft, positioned it at her opening, which was dripping already, and he pushed in all the way.
Shelly gasped, then with a sexy moan, said, “Fuck me, stud.” He took no mercy on her, fucking Shelly like an animal; he pounded her through at least 3 screaming orgasms. Shelly was yelling at him to fuck her harder; he’s slamming into her, just battering her pussy, when he pushes in deep, holds there. I can see his balls pull up, his cock flexing; he groans, “Take this, bitch,” as he pumps Shelly full of cum. His cum is leaking out around his shaft, running down to her cheeks, pooling on the bed.
As he pulls out, Shelly yells, “Get over here, Dick; don’t waste any. Lick it up.” I wasn’t planning on this, but did as she asked. I knelt down and just licked and sucked his cum from my wife’s pussy till she pushed me away. Shelly got up, pulled on her shorts, grabbed my hand, looked at him, said thanks, and we walked out.
After we were back in our room, I wanted to reclaim my wife. As I pushed my cock into her, I could tell she was really stretched out. It still only took me about 3 minutes to cum, as the whole experience was running through my head.
A few months have gone by since our wedding; we’re both heavy into work. We frequently talked about our honeymoon experiences. Shelly wanted to know if I was open to swinging with bi couples, having same-gender sex, maybe even a gay or lesbian fling. After a lot of discussions about it, I agreed to follow her lead and would do whatever she set up.
Over the next few months, we did meet some couples for sex; I did get to fuck my first man. It was okay, but I did prefer to be the one getting fucked by a man. That’s when Shelly started telling me about the new drug her work had been experimenting on, that they had started trials with people, and it was going well.
Another month went by; Shelly came home on a Friday. It was a 3-day weekend, Labor Day. She told me she had a surprise for us. Shelly laid out on the table two pills; one was blue, and the other was pink. She explained to me that they were gender-change drugs. The blue one would change a woman into a man, and the pink one would change a man into a woman.
She went on to tell me that we keep our own mind; only the body changes. It lasts up to 48 hours, depending on the individual. We take them tonight and wake up in the morning a different sex. I was skeptical, but Shelly reassured me it was safe.
That night, just before bed, I took the pink pill, and Shelly took the blue pill.
That night I had some weird dreams, ones I couldn’t exactly remember. The morning came, I woke up first, and the very first thing I noticed was a heavy weight on my chest. I had tits. I reached down to check, and yes, my cock was gone; in its place was a slit. I rubbed my finger up and down a few times when I realized I needed to use the bathroom. Getting up and padding across to the bathroom, it was a different experience, not just sitting to pee, but feeling the warmth and stream against my pussy lips; it was actually exotic to me.
Back in the bedroom, Shelly had woken up; the covers were thrown back, her morning wood was standing up straight and proud, and she had a hand wrapped around her balls. As I stood and admired her manhood, I thought it looked to be longer and thicker than mine was, or I should’ve said had been. Shelly grabbed my hand and said, “Here, Dick, hold it.” Holding it wasn’t the only thing I wanted to do, so I bent over and licked up and down a few times, then I took Shelly’s cock in my mouth, sucking it as deep as I could, holding her balls in one hand, and wrapping the other hand around the bottom of her shaft.
The experience was so new to Shelly that she orgasmed in a few minutes. The cum shot out like a cannon; a huge load of cum filled my mouth. It was bitter. No matter, I swallowed it all; it took 3 gulps to get it down. The look on her face was one of pure bliss. She uttered, “I could get used to that.”
Back in bed, we cuddled for a while, until I noticed her cock was getting hard again. So down I went; I wanted to taste it again. Her cum was what I wanted. Shelly had other ideas; she wanted me on top. Licking me was her goal. The first swipe of her tongue up my pussy was a jolt of pleasure. When she parted my lips and swiped her tongue up and down, then lightly sucked them into her mouth, kissing all over my inner legs and my bottom. When she finally ran her tongue up and over and around my clit, I squirmed and froze; the pleasure was instantly intense. Shelly knew what I wanted and how to give it to me.
We played with each other a long time; she drew out my orgasm, as only she could. I felt my body go into spasm; I could only bury my face in her groin. When that orgasm hit, I cried out, almost weeping from the intense pleasure she gave me.
The orgasm was so intense, I rolled off her, lying on my back, lost to the world. That was when I felt Shelly move; then she spread my legs, moving between them. I was becoming aware that her cock was pushing into me; it felt so big. I arched my back as I looked her in the eyes; the only words came from Shelly: “Dick, take my cock.” She pushed in; I felt the pressure, then the stretch, a slight pain, then she was fucking me deep, pushing on something deep inside; the feeling was like nothing I had ever experienced before. Before I knew what was really happening, I had this feeling; it was expanding throughout my body. I felt it from my toes to my forehead. Next was a heat inside my pussy, hot, so very hot; I felt her cock expand, then the pulsing of cum shots, filling me up. My orgasm was hard, screaming, body locking up, then euphoria, heavy breathing, finally a collapse.
We cuddled forever, it seemed; I could feel Shelly’s cock getting hard again, then she was licking me again. I had to push her away; I was just too exhausted to fuck or suck again. I wanted to sleep.
A few hours later, after a shower and admiring my female body, I felt shorter, my tits seemed big, my pussy was covered with hair, my bottom was peach-shaped. I walked into the kitchen; Shelly was making lunch. She was naked; I was checking her out. Her cock hung down about 6”; her balls were heavy; she had pubic hair, chest hair, and somewhat long hair. She looked taller.
As we ate lunch, Shelly was talking about how we needed to be cautious, as it was possible I could get inseminated and pregnant, which would make this very awkward, as I would not change back on Sunday night. I would remain, stay, a woman for life.
We talked about sex, how it felt; she was excited to feel more male ejaculations, blow jobs, hand jobs, fucking. She wanted to fuck my butt, anal sex. I was curious about that also; I knew what it felt like as a man to be on both ends, being fucked and fucking an asshole. I also wanted to feel it as a woman.
That night we had anal sex, exclusively. Shelly fucked my ass, then I fucked Shelly’s ass with the Feeldoe. I must say having my ass penetrated as a woman was different; yes, I did orgasm, yes, it felt different. I enjoyed it, and I recommend that every woman experience it at least twice. Why? Because the first time, it’s hard to relax enough to enjoy the penetration.
On Sunday night we only did oral sex; I enjoyed having Shelly’s tongue and fingers in me almost as much as her cock. After suckling her to multiple orgasms, I did come to like the taste of cum. The other part I liked was eating her ass first, then sucking her cock while I rubbed her prostate; the orgasms she had from that were violent.
I was relieved on Monday morning to feel my cock again; the transition from female to male was complete. Although I think Shelly was disappointed, she liked having the cock, being the one who was the primary penetrator. Over breakfast, Shelly expressed a desire to repeat events of the weekend.
A couple of months went by. When Shelly came home from work one evening, super excited, they had a breakthrough: another team had achieved a new X-pill that would last 7 days. That night Shelly pegged me with the Feeldoe; she really pounded me to a prostate orgasm, then she rode my face to a massive orgasm, squirting and drenched my face and the bed.
The next morning, Shelly started asking me about taking a vacation, going back to where we stayed for our honeymoon; she wanted us to use the week-long X-pill. She wanted to have threesomes, foursomes, and moresomes. I wasn’t sure about all of that, but Shelly always gets what she wants, one way or another.
I was concerned with the risk of getting pregnant, so we prepared: condoms, spermicide, and a diaphragm. Shelly secured the pills about a week before our trip. We planned the vacation for 10 days. One day for the flight, we had to be our normal gender, passports, you know, then a couple of days after the change back, and flight home, passports, you know.
Shelly had taken measurements of me when I was a woman, and of herself as a man. We bought new clothes, female for me, male for her. She bought all the clothes; all of mine were very sexy, revealing. She wanted heads to turn when men and women looked at me. Hers were somewhat conservative, except for the Speedos; I’m sure they were a size smaller than they should have been.
Upon arriving, once in the hotel, we took our respective pills and went to bed. Shelly sucked my cock; little did I know it would be my last blow job for quite a while.
We woke up the next morning, changed. My female body looked the same. Shelly looked the same, although her cock looked bigger to me. Yes, I measured it: 8” and 7” circumference. Damn, a real pussy and ass stretcher!
I was still holding it when it twitched in my hand. Shelly’s new cock was already filling out, the head swelling dark and fat, a thick vein running down the underside. She was staring at my tits as she’d never seen them before. I guess, in a way, she hadn’t—not from this side.
“Get up here,” she said, voice lower than it used to be.
I crawled up the bed. My new tits swung heavy and full; the nipples were already tight. Shelly grabbed one, squeezed it, then sucked it into her mouth like she was starving. The pull went straight down to my cunt. I could feel myself getting wet, that new slick heat between my legs I still wasn’t used to.
She flipped me onto my back and pushed my thighs apart. No teasing this time. She just dove in, tongue flat and wide, licking from my asshole all the way up over my clit in one long, sloppy stroke. I gasped and grabbed her hair. It felt different as a woman—sharper, wetter, like every nerve was sitting right on the surface. She sucked my clit between her lips and flicked it hard. Two thick fingers pushed into my pussy at the same time. I was already soaked; they slid in easy.
“Fuck, you’re dripping,” she muttered against me. “Taste yourself.”
She crawled up and kissed me, shoving her tongue in my mouth so I could taste my own cunt. Then she lined that fat cock up and pushed.
The stretch was immediate. Even after the first weekend, I wasn’t ready for how thick she was now. The head popped in, and I made a sound I didn’t recognize—high and broken. She didn’t stop. She kept feeding it into me, inch after thick inch, until her balls were pressed against my ass and I felt her in my stomach.
“Take it,” she growled. “That’s your cock now, Dick.”
She started fucking me. Slow at first, long strokes that dragged that fat ridge over whatever the female version of my prostate was. Every time she bottomed out, I saw stars. My tits bounced. She grabbed them and used them like handles, slamming into me harder. The wet slap of her hips against mine filled the room. I could hear how sloppy I was getting.
I came the first time with her cock buried to the hilt, my pussy clamping down so hard she cursed. She didn’t stop. She just kept pounding through it until I came again, then a third time, each one rolling into the next until I was shaking and crying and telling her I couldn’t take any more.
She pulled out, flipped me onto my stomach, and shoved a pillow under my hips. Two fingers smeared lube on my asshole—plenty of it—then that fat cock was pressing there too.
“Breathe,” she said.
I did. She pushed. The burn was worse than my pussy had been. I felt myself open around her, slow and reluctant, until the head popped through and she slid the rest of the way in one long, relentless stroke. I made a raw sound into the mattress. She started fucking my ass the same way she’d just fucked my cunt—deep, heavy, no mercy.
Every thrust shoved my clit into the pillow. I came again with her cock in my ass, a different kind of orgasm, deeper and dirtier. She felt it and started slamming harder, chasing her own. When she came, she buried herself and held, cock pulsing, pumping load after load into my guts. I could feel the heat of it, the way it leaked out around her shaft when she finally pulled out.
She rolled me over, still hard, and shoved her cock back into my mouth so I could clean it. I sucked her until she was dripping with my spit and her own cum. Then she pulled me up and kissed me, sharing the taste.
We stayed in bed until almost noon. She fucked me twice more—once in the shower, standing up, my back against the tile, one of my legs hooked over her arm while she pounded my pussy and sucked on my tits. The second time she sat on the edge of the bed, and I rode her, facing away so she could watch her thick cock disappearing into my ass. I came so hard I almost fell off.
When we finally got dressed, I put on the clothes she’d bought me. Tiny white shorts that rode up my ass and a thin white tank with no bra. My nipples showed through the second I moved. Shelly wore a pair of those too-small Speedos under loose shorts. The outline of her cock was obscene.
We went down to the clothing-optional beach. I felt every pair of eyes. Men, women, couples—people stared at my tits, at the way the shorts cut into my pussy, at the way Shelly’s hand stayed on my ass as she owned it.
We found a spot near the same area we’d used on our honeymoon. Shelly stripped first. That heavy cock hung down, half hard already from watching me walk. I took my time taking the shorts off. When I bent over to lay out the towel, I knew people could see everything.
A couple we’d seen the night before walked over. The woman was blonde, mid-thirties, small tits, shaved. The man was older, thick through the chest, cock already fat. They didn’t even pretend they weren’t looking.
“Mind if we join you?” the woman asked.
Shelly looked at me. I nodded.
They laid their towels right next to ours. Within ten minutes, the woman had her hand on my thigh. The man was talking to Shelly about the pills, about how long they lasted, about how good my ass looked. I could feel myself getting wet again just from the conversation.
The woman leaned in and licked my nipple through the tank. I didn’t stop her. Shelly reached over and pulled the tank up so both of them could see my tits. The woman sucked one; the man sucked the other. I lay back on the towel and let them.
Shelly pulled her Speedo down. That thick cock sprang out, already leaking. The blonde woman looked at it, then looked at me.
“You take all that?” she asked.
“Every inch,” I said.
She smiled and dropped her mouth on it. I watched her struggle the same way I had that morning. Shelly’s hand went to the back of her head and pushed. The woman gagged, pulled off, spit running down her chin, then went back for more.
The man moved between my legs. He didn’t ask. He just pushed two fingers into my cunt, felt how wet I was, then lined up and shoved in. I was still loose from the morning, but he was thick enough that I felt it. He started fucking me right there on the beach while his wife sucked my husband’s new cock.
People were watching. I didn’t care.
Shelly pulled the woman off her cock and nodded at me. The woman crawled over and sat on my face. I ate her while her husband fucked me. She tasted sharp and sweet. When she came, she ground down hard, and I swallowed whatever she gave me.
Shelly moved behind the man, and I felt the towel shift. A second later, the man groaned, and his rhythm changed. I knew that sound. Shelly was fucking him. I could hear the wet slap of her hips against his ass while he kept pounding my pussy.
The four of us stayed like that until the man came inside me with a grunt. Shelly kept fucking him through it, then pulled out and shoved her cock into my mouth so I could taste his ass and her cum together.
We didn’t last long on the beach after that. Too many people were gathering. We packed up and went back to the suite.
The blonde woman and her husband came with us.
Inside the room, it got messier. Shelly bent me over the couch and fucked my ass while the woman lay underneath me, licking my clit and sucking on my tits. The man stood in front of me, and I sucked his cock, tasting myself on it. When Shelly came, she pulled out, and the woman immediately licked the cum out of my ass. Then the man took her place and fucked my ass while Shelly sat on the couch, and I rode her cock, bouncing on that thick shaft until I came so hard I squirted down her balls.
They stayed the night.
By the time the sun came up, I had lost count of how many times I’d been fucked, how many loads were inside me, how many times I’d come. My pussy was swollen. My ass was sore and leaking. My tits were covered in bite marks and dried spit.
Shelly looked at me from across the wrecked bed, that fat cock already starting to fill again, and smiled.
“Six more days,” she said.
I reached for her.
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