Anal play was something that was never discussed early on in our relationship. In fact, we pretty much assumed that the ‘back door’ was completely off limits. Although we loved sex toy play, we didn’t have any anal toys in our personal toy box. A couple of years later, our thoughts about anal play changed in an unpredictable way. We’d like to share our story about our first time with anal play.
How the idea got started
Robin: I love reading erotic fiction. Many of the stories that I’ve read include anal play and anal sex scenes. After reading several stories, anal play started to seem more and more interesting to me. The descriptions of the anal scenes were very detailed and the characters seemed to love what was happening to them. As I read several more stories, I started to become very aroused with the idea of anal play. Although it seemed really hot, I was still afraid to try it myself. Also, I wasn’t sure how to approach the subject with Liam. I’ll let Liam tell you more…
Liam: I remember Robin sitting in our recliner on a Saturday morning with her face buried in her Kindle. I started cooking breakfast and, once finished, I politely asked her to come into the kitchen to have breakfast with me. While we were eating, I asked Robin what she was reading. She told me that she was reading a book about two lovers that were into light bondage. This piqued my interest so I asked Robin to tell me more about it. She described the scene and went on to tell me how the female character was submitting to her husband and they were having anal sex. As Robin was describing the scene, I noticed that she seemed either bothered, or aroused, by it…it was really hard for me to tell. Her cheeks were red but the rest of her body looked flushed and pale. I reached out and touched her skin which felt very clammy. I asked her if she was feeling okay and she confirmed all was well. It was at that time that she told me that she’d found the scene to be very “hot” and had been sweating a bit while reading. I was really surprised by the conversation that followed.
How we communicated the idea
Robin: After describing the anal scene to Liam, I decided to softly approach the subject with him. Upon telling him how hot the scene was, I mentioned that I was very curious about anal play in our own relationship. I continued to tell Liam about several other scenes I’d read from previous books. All of these scenes, for one reason or another, were etched into my brain. As I was describing all of the scenes to him, I could tell that he was interested by his posture. He was leaning in close to me, eyes locked on mine, and with raised eyebrows. After I finished describing all of the scenes that raced through my mind, I straight-forwardly asked Liam, “Do you have any interest in trying anal play?” I couldn’t believe those words just came out of my mouth! I figured that Liam would receive the question with much openness…what man wouldn’t? I’ll never forget Liam’s response.
Liam: I was in complete and total shock when Robin told me that she was curious about anal play. Early on when we first met, she briefly mentioned that her ass was an “exit only.” I quickly responded to Robin’s question with, “Of course I’m interested!” I could tell after answering that she was relieved to hear that I was interested. We continued talking about anal play for the next half hour or so. We both expressed our own opinions, and both of us agreed that we were scared to try it. We wanted to make sure that our first time would be perfect. Little did Robin know, I’d already read several “how to” articles on getting started with anal play. I ended up telling Robin this and also mentioned that we would want to educate each other and put a plan in place prior to our first experience.
How we put our plan together
Robin: I was a bit relieved when Liam told me that he had already researched anal play. We discussed everything…I mean EVERYTHING. We covered several topics: being ‘clean’, fingering and toying, patience, pain vs pleasure, lubrication, and communication during and after play. After discussing each topic, I knew that I wanted to move forward with anal play. I ended up telling him that I wanted to give it a try, yet I was very scared about our first time. Liam also expressed that he’d like to move forward. However, I was very surprised by what Liam said next.
Liam: I really appreciated that Robin came forward about her interest in anal play while simultaneously expressing her fear. I was taught early in life to always lead by example. My personal philosophy: never force someone to do something that you wouldn’t first do yourself. With that said, I asked Robin, “Since you’re scared, would it be okay if I receive first?” Robin was really taken off-guard by my response. I think she was under the impression that anal play was going to be one-sided and that she would always be on the receiving end. Robin ended up telling me she was relieved to hear that I was also willing to receive anal play. My personal opinion is that experiencing both sides of anal play makes you a better giver and receiver. Robin soon agreed that she’d like me to be on the receiving end first. We ended up discussing when the first time would take place and agreed that we would try the following Saturday.
How we prepared for our first experience
After finishing our conversation, the two of us enjoyed the rest of our weekend together. On Sunday evening, we went online and shopped together for a few small anal toys to use the following weekend. Monday morning came quickly and we both went back to work as usual. After having several busy days at work, Friday had finally arrived. We ended up meeting for lunch during a work break and had a nice meal and conversation. Since we were going to play the following day, we wanted to ensure that we would be as clean as possible for our first time. With that said, we agreed that our lunch would be the last thing we would eat until after our anal play experience was over. We didn’t want to engage in anal play with a full stomach or bowels. After lunch, we resumed back to our jobs to finish the workday. After arriving home from work, a box was sitting on our front doorstep. We brought the box inside, opened it together, and discovered that our anal toys had arrived. We thoroughly looked them over, had some laughs, and cuddled up and watched a movie. Friday eventually passed and we both woke up Saturday morning in anticipation for our first anal adventure.
Here’s how each of us prepared for our new adventure:
Liam: I wanted to be as clean as possible so our first time would be as enjoyable as possible. I didn’t want Robin to be grossed out by the sight of poop so I ended up giving myself an enema. It’s recommended to wait a couple of hours after having an enema before anal play should begin. Once cleaning myself on the inside, I then proceeded to take a shower. After my shower, I set up our Love Altar (massage table) in our living room. After the table was set up, I then went to our personal toy box and grabbed some water-based lube and the new anal toys we received the previous day. The scene was set, now all I had to do is wait for Robin to get ready.
Robin: Similar to Liam, I also gave myself an enema followed by a refreshing hot shower. Once I was finished getting cleaned, I walked out to the living room and saw a beautiful arrangement of sex toys, lubrication, and massage oils on display. Our massage table was set up, the window blinds were closed, and a few candles were lit. Liam did a great job setting things up and our play area was very relaxing and inviting. I was a bit nervous about what lied ahead, but I knew Liam was going to take good care of me. As it turned out, Liam ended up giving me a full-body massage to relax before beginning our anal adventure. After my massage was over, we commenced our anal play.
Liam’s first anal play experience
Robin: I first had Liam lay face-up on the table. I grabbed some massage oil and massaged his front side from head to toe. After doing so, I had him roll over onto his stomach and proceeded to massage his entire back side. Once finished with his massage, I asked him if he was relaxed and ready. He muttered, “Uh huh.” I stood at his left side just above his waist looking forward towards his feet. Using both of my hands, I now concentrated solely on his butt. I deeply rubbed both cheeks for a few minutes. Then, I spread his cheeks open exposing his nice little puckered hole. Again, with both hands, I rubbed the tips of my fingers through the crack of his butt and continued past onto his perineum. I continued to rub back-and-forth through this area for a few minutes. Liam was enjoying it a lot as he was starting to breathe more heavily.
Once I could tell that he was really warmed up, I started circling around his pucker with just my middle finger. Every now and then I would cross directly over top of his hole. Liam started to breathe even harder. Still using my middle finger, I completely stopped circling and started to target the center of his butthole. Before doing so, I lubed up my finger and poured a generous amount of lube directly onto his rosebud. Using slight pressure, I started poking my finger into his hole. After a couple of pokes, I left my finger tight against his hole without any further movement. His ass suddenly relaxed and my finger sunk deeper inside up to my finger’s first joint. I pulled out slightly and then entered again going slightly deeper this time. After 6 or 7 of repetitions, my finger was as deep as it could go. Then, I used my finger in a gyrating motion to help loosen him more. While do this, Liam was moaning, sighing and breathing very quickly. I checked back in with him to see how he was doing. His reply, “It feels good, don’t stop, I love you.” With a smile on my face, I continued to finger his asshole for a few more minutes.
Once finished, I had Liam flip over so he was facing up. I grabbed one of our new anal toys. This toy looked like a g-spot dildo with a very narrow shaft. I lubed the toy and then went back at his hole for more. As I was toying him, his cock became hard very quickly. I continued thrusting the toy faster, then slower, then faster. Liam was moaning with pleasure. Within a few minutes, I could tell he was getting close to having an orgasm. Wrapping my hand around his cock, while toying with the other hand, I started stroking him. Within a minute or so, Liam shot a huge load of cum while letting out an animalistic roar. It was so hot! I continued stroking him and eventually removed the toy. I moved up to his face, leaned over, and gave him a kiss. I rubbed his chest and allowed him to rest for a few minutes before cleaning up and switching places.
Liam: My first time was absolutely amazing! Robin did a great job with her hands. She was really good at communicating with me to ensure I was always comfortable. The experience was not at all painful. Robin remained very patient and made sure I was properly warmed up. As she was fingering me, I could feel myself loosening up with each stroke. The toy definitely put me over the edge since the curved end rubbed against my prostate. I could feel each pass that the toy made across my prostate and it felt wonderful! The part of the experience I enjoyed most was having my ass played with while having my cock stroked. Stimulating multiple erogenous zones at the same time was difficult to handle but was different from anything I’d ever felt before. Overall, I knew that future anal play was a solid “Yes” vote from me.
Robin’s first anal play experience
Liam: I’m very thankful for volunteering to receive first. Robin was a good teacher and made my experience better than I could’ve ever imagined. Now, the pressure was on me to provide the same amount of pleasure to her. Similar to my experience, I started by having Robin lay on her stomach. She’s pretty lucky as she got a second back massage from head to toe to help her relax. After the massage was finished, I did the exact same thing to her as I had received. I started with her butt cheeks and crack, then to circling around her anus, and eventually ended up with my entire finger inside. She gave out a few really sexy moans and was breathing heavily. I wanted to change things up and not do the exact same activities that were done to me.
Once I finished with the finger, I had Robin move to her hands and knees. Our massage table is fairly long and wide which gave me perfect access to her entire backside. The view was pretty amazing too! With Robin on all fours, I grabbed our We-Vibe Tango and pressed it against her clit while simultaneously fingering her cute little pucker. It was extremely sexy as she started to rock back and forth on my finger. I used a gyrating motion with my finger eventually loosening her up more. I pulled my finger out and grabbed for another of our new toys. This was a slender dildo that was similar to the shape of a penis. The toy was at least double the girth (if not more) of my finger and slightly longer. For several minutes, Robin rode the toy while still having the Tango buzzing against her clit. She was moaning loud, almost screaming…again, very sexy! She ended up having an intense orgasm. Just as I thought things were coming to an end, Robin demanded, “I want you to fuck me hard.”
Robin moved forward on the Love Altar so I could join her. Before climbing up, Robin begged for me to put a plug in her ass. Our third toy we ordered was actually a set of three anal trainer plugs. Looking at the three of them lined up side-by-side, I knew the first was too small so I reached for the middle one. I lubed it up, put some more lube on my hand, and then climbed up behind her on the table. I took the lube in my hand and reapplied it on her cute little pucker and then gently pushed the plug inside. Robin moaned as her gorgeous ass swallowed the plug. Then, I entered her and started to move in-and-out very slowly. The plug had a convenient little ring attached to its base. I slid my finger through the ring and grabbed her left hip with my free hand. I started thrusting faster and faster while simultaneously gently tugging on the plug’s ring. Robin was moaning really loud and started pushing back against me. I kept a constant pull on the plug’s ring and before I knew it, I had stopped thrusting altogether. Now, Robin was rocking back-and-forth banging her beautiful backside against my pelvis. She kept rocking harder and faster when suddenly she let out the loudest moan/scream that I’ve ever heard. Orgasm number 2…check! After her orgasm, I gently pulled the plug out and climbed off the table. Robin looked exhausted so I helped her lay back down on the table to rest. I didn’t even have to ask her if she liked it, but I did anyway. Her response, “Oh my god, mmmmm…”
Robin: My first time was better than I could’ve imagined. Liam did a great job and, in my opinion, was due to having such a wonderful teacher (wink, wink). Seriously, I was really nervous as I was climbing up on the massage table but Liam soon had me feeling at ease. He was also very patient with me and did not do anything too fast nor too hard. Pain was on the forefront of my mind. Surprisingly, it felt really good. There was some uncomfortable pressure at first, but certainly no pain was felt. I was expecting to receive almost the exact same experience that I gave him. That was not the case at all. I loved the fact the he used a clitoral vibrator along with the other new toys that we purchased. The anal dildo felt amazing and was not too big nor too small. Like Baby Bear’s porridge, it was just right! Everything felt wonderful, however, I always love having Liam inside me. The combination of his cock and the plug, it left me with an earth-shattering orgasm. Like Liam, future anal play was a solid “Yes” for me too!
Our first anal play experience, to that exact point in time, was the most intense sexual experience that we ever had. To date, it still ranks in our top ten. Since our first time, we’ve continued on with anal play. We’re no longer novices and have graduated to experts over the last couple of years. We now play with larger toys, perform anal sex, rimming, and have included pegging into our bedroom adventures. Anal play has helped improve our communication and our trust in each other. We always discuss what’s going to happen beforehand and debrief when our play is over. Additionally, our trust in one another has improved as we know we’re going to be cared for. For us, anal play is sacred, sexy, and lots of fun!
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