Rocky and I had been lovers for several months and had hit a nice groove. He enjoyed my blowjobs and I loved servicing him while dressed in panties, stockings and heels. After one of our sessions, we were lying in bed, him enjoying the post orgasmic afterglow and me lying beside him savoring the exquisite salty-sweet taste of his semen that I'd just swallowed. As I ran my fingers through his chest hair, he looked over at me and asked if there was anything sexually he could do for me. Without hesitating, I said I wanted to receive anal sex from him.
He laughed and said "Well, ya just blew out my pipes buddy, but how about we make some plans for it?"
"That sounds nice!" I said as I looked up at him and smiled.
A few days later Rocky messaged me. Instead of his usual "You hungry?" text, this time he wrote "OK if I come to the back door this time?" I laughed as I wrote back "It'll be unlocked for you." We made plans to meet up that evening.
I'd experimented with anal since I was a teenager with various objects and had used a dildo with my first gay lover, but I'd never bottomed and had my lover's cock in my ass. Rocky wasn't particularly large regarding length or girth (some of my toys were bigger than his penis), so I knew I'd be able to accommodate him and was looking forward to having sex with him this way. I loved the submissive feeling of pleasing him orally and wanted to explore that in another way. I hoped he'd cum inside of me as I liked the thought of him as a dominant animal with his spunk claiming me as his sexual property.
Though I'd never received anal sex with a man, I had a pretty good idea of how to prepare, my objectives were being thoroughly cleansed, very relaxed and well lubricated. Several hours before we were to meet, I gave myself two enemas. I loved the feeling of preparing for him and I knew from past experience to take things slow. After the second enema, I picked out what I'd wear for Rocky. By this point, I'd gotten into the habit of dressing in panties, stockings and heels for him when I had sex with Rocky (see my previous story), and this wasn't going to be different. Since I thought (and hoped!) there'd be some acrobatics with Rocky positioning me the way he wanted me, I decided to wear a sexy body stocking that was crotchless. It was black and the legs had a pattern that flattered my long legs. I picked out some lovely pumps with a snakeskin look and some sheer black panties to hear over the body stocking. After I'd picked out what I'd wear, I took a shower to clean up from the enemas and shave my legs. I also took one of my favorite dildos in the shower to help me prep.
The water was very relaxing and I took my time shaving, making my legs smooth and luscious. I washed off my backside, lubed up my fingers, started massaging my anus, and gently probed with my fingertips. Starting with one finger and gradually working up to three, I could feel the initial tightness and resistance of my sphincter lessen as I worked myself. It felt great getting ready for my lover this way and I imagined Rocky's cock sliding into me. When I felt sufficiently loosened up, I lubed up my dildo, bent forward a little, and brought it around to my anus. The head popped past my sphincter with just a little resistance and the sensation of being opened created a warm sensation in my pelvis and sent a tingle up my spine. The first few inches had been stretched by my fingers but the resistance increased slightly as I advanced. Going slowly, I was able to work it in, til all 7 inches were buried in my ass. The fullness was very nice and I could feel it against my prostate. There was no pain so I held it there for a minute or so, then slowly withdrew. The head felt as good going out as it had going in and I was pleasantly surprised to find no fecal residue. I lubed up again and then reinserted the dildo, able to go faster this time and easily get it to the base. Taking it out, I repositioned myself, squatted, and inserted the dildo again. In this position, I could start thrusting it in and out more forcefully, which was feeling better and better. On one of the strokes, it popped out and a little bit of residual water from the enemas came out, without any residue. I repeated this a few times to get any remaining water out, cleaned up my ass and the dildo, then got out of the shower.
I was feeling a nice combination of anticipation and relaxation after the cleansing, shower and butt play so I lolled about the house naked for a bit. As the time for Rocky to arrive drew closer, I applied some lotion to my legs and slipped on the body stocking. It felt great sliding up my smooth legs and I loved the look and feel as I adjusted it. I slipped on a lovely sheer black high waisted brief, stepped into the heels and put on a light black t-shirt to complete the look. I also got my bed ready by putting out some towels, washcloths, and some lube, all within easy reach.
I have a selection of butt plugs and planned on using one for preparation. As a practical matter, I thought it would help keep my sphincter loosened and prevent it from tightening back up. On an erotic level, knowing that my anus was being held open for my lover turned me on. I fantasized about how it would feel to open the door and greet him with a butt plug in place. I figured that since I'd already loosened myself up a bit, I could skip the smallest plug and so got the next biggest size, lubed it up, positioned myself on my bed on my knees with my ass in the air, probed gently with the tip, then slipped it in. There was no resistance as it went in and I loved the sensation of my sphincter gripping the base as I let go. I got up and walked around a bit, feeling submissive with the plug in place. The plug moved slightly as I walked, gently massaging my prostate and causing some fluid to ooze at the tip of my cock. Over the next 30 minutes or so, I worked up to the 2nd biggest plug I had. It took a little bit of persuasion to seat it, but there was no pain whatsoever, the stretch of my sphincter was magical, and I felt *very* full with it inside. I could still walk around without discomfort, so I went over near a window for some natural light and took a pic of my legs and heels. I sent it to Rocky with a simple "I'm ready!" He replied that he was on the way.
I sat by the front window awaiting him and pulled up some gay porn. Watching it always got me worked up as I thought about how much I'd like to be the one sucking a lovely rock hard cock and swallowing cum. I was looking at a scene with gentle anal sex that was very nice when Rocky pulled into the driveway. I shut down the computer and went to the front door to greet him. Walking with the plug in place made the tip move slightly against my prostate, causing some precum to leak from my rock hard cock, which strained against my panties. Standing behind the door to shield myself from any curious neighbors, I demurely greeted Rocky as he stepped inside.
"Hey, lover!" I said.
He smiled as he looked me over then looked down and saw my cock bulging the sheer fabric of my panties. "Looks like my cocksucker is pretty excited to see me." he said.
"As always!" I replied, reaching out to rub my hand on his crotch. As I felt the hardness under the fabric, I laughed and said coyly "Feels like I'm not the only one!"
He smiled as we embraced and I imagined how it would feel to hold each other like this with his cock inside of me. We held hands as we walked back to my bedroom.
Standing by the foot of the bed, I looked into his eyes as I unzipped his pants, smiling as I discovered he didn't have any underwear on. Wrapping my hand around his cock, I went down on my knees and assumed the position I love so much. He was erect and not yet fully hard, with a drop of precum at the tip. I flicked my tongue across the head and savored the taste.
"Mmmmm...." I moaned, then opened my mouth and slid his cock in, going all the way to the base in one smooth motion.
He shuddered and groaned as I enjoyed one of my favorite parts of giving head, the first caress of my lips on the glans, followed by the warm, familiar feeling of a semi-erect cock filling my mouth, and the soft head lodging in my throat. Rocky's erection came quickly and easily to him and I loved the sensation of his now firm cock as I sucked up and down the shaft.
"Jesus buddy! You give the best blowjob I've ever had! It's like you were born to suck cock." he said.
I loved knowing that I was pleasing him and went all the way down his shaft, gagging slightly as the now firm head entered my throat but holding his ass firmly as I pushed past it and buried my face in his crotch.
"Easy!" he said, "Remember what I'm here for today. You don't want me to cum too fast."
