Exploring My Bi Side Ch. 02

Randy and I kept up our meetings, sometimes weekly sometimes two or three times a week, just depended on our schedule and how horny either of us were. We always met at his house in his home studio which offered us a lot more privacy and freedom. As I had stated the massages pretty much stopped but he would still give me one when I needed one or just wanted one. When I would request a massage I'd lay on his table on top of a towel nude. Randy would give me a full body always including his massaging and fingering my asshole. This always drove me insane and would always give me the most intense orgasms.

One day while getting a massage Randy said "You always keep your pubic hair and balls trimmed and shaved, have you ever thought of shaving your ass?"

"I have shaved it in the past, but as you can imagine its not the easiest thing to do."

Randy replied "Would you let me do it for you and you can do mine?"

As his fingers worked over my asshole "If you really want to, I suppose you can." was all I could say.

Randy said "Great, I'll be right back." A few minutes later he returned and said "Roll over." As I rolled onto my back I saw Randy was carrying a bowl with hot water with a washcloth in the bowl, shaving cream and a razor. He took the washcloth, rung out the excess water and placed it over my pubic hair and cock, he took a second one and wrapped it around my balls. After a few minutes he removed them and began to lather up the area with the shave cream, his hands really massaging my cock and balls began to make me hard.

Randy began to shave me, I never shaved my pubic hair completely smooth before but here I was letting him do it. Randy continued shaving all of the hair from my pubic area, base of my cock and my balls. By the time Randy was washing the excess shaving cream my cock was rock solid, he leaned over taking the head between his lips giving it a quick suck then letting the head pop from his mouth saying "You'll have to wait for that, now roll onto your stomach."

After rolling over Randy pushed my legs apart and placed the washcloths between my cheeks. I couldn't believe I was letting him do this, it felt a little odd, I felt a bit exposed knowing he was going to be looking at my asshole. I know it was weird being he had played with and fingered my ass numerous times by this point, so I just let it roll. After several minutes I felt Randy remove the washcloths and then heard the shaving cream being applied to his hand then I felt it being applied to my ass crack. I felt the razor begin to slide along my ass, Randy's hand spreading my cheeks, allowing him better access between the cheeks. I reminded him to be very careful and not to cut me.

After several minutes Randy instructed me to kneel on the table, I was very hesitant, made me feel very vulnerable, but be reassured me and got me to relax and soon there I was kneeling as my ass was just inches from his face as he continued shaving me. I felt the washcloth cleaning the excess shaving cream and began to thing this is almost over. Once Randy had cleaned the remaining shaving cream, he poured a little oil into his hands and began to massage the oil into my ass, taint, balls and cock. He was massaging every area he had just shaved. He started stroking my already hard cock his free hand massaging my balls, then my ass. Soon his finger was in my ass as he continued stroking my cock. I knelt there enjoying everything, it felt so much better being completely smooth, like everything was more sensitive.

As Randy's finger slipped out of my ass I felt his hot breath as his tongue replaced his finger, his hand still stroking my cock as he ate my ass. A loud moan escaped my lips as his tongue licked around my ass, pressing against my hole. My moaning must have encouraged Randy. The more I moaned the more he licked, the effect he was having on me was directly effecting the way he ate my ass. I was so close to cumming, I told Randy I was close which caused him to snake his tongue inside my ass, stroking my cock faster. As my moaning turned into screams, Randy gripped the head of my cock tight, and continued pumping my cock, not allowing my cum to escape but build up in the shaft, as my moaning subsided a little, Randy placed his mouth at the head of my cock and loosened his grip allowing my cum to shoot into his mouth, then sucking the head, getting out every last drop. He looked up at me and said "I love your cum."

I took several minutes to recover from my orgasm, it was probably one of the most intense of my life. I threw on my boxers and a t-shirt as Randy poured us a couple beers from his bar. After 2 beers Randy said "OK, time for you to shave me." I have never shaved anyone, I was a bit nervous overthinking this as Randy was changing the water and getting a new washcloth. He returned, placed the bowl on the side table and jumped up on the table. I just did what Randy did to me, I took the washcloth, covered the same areas he had done to me, waited several minutes then lathered him up, I loved feeling his cock grow in my hand as I lathered his cock and balls. Randy really has a nice cock, cut, a little thicker than mine. When soft its about 5" and still pretty thick, when hard it gets to about 7/7.5" and just a little thicker compared to his normal state. Where as I am also cut, but when soft I'm smaller and thin, when I am hard I'm about 6.5/7" and fairly thick. Anyway, I continued stroking Randy's cock much longer than I needed to just to later him up, he definitely didn't seem to mind. I began to shave him slowly being very careful not to cut him. I took several minutes to shave him completely smooth as he had done to me. When I was finished, I cleaned the excess shaving cream, I was surprised how much nicer his cock looked all cleaned up, I stroked him and then leaned in taking his cock between my lips. It felt amazing, so smooth, no hair, just pure smoothness. I sucked that beautiful cock for several minutes until Randy pushed me off saying, "You're not done yet."

Randy rolled over onto his stomach and spread his legs without hesitation. This was the very first time I really saw his ass, I really was never drawn to a man, for me it was more about stroking and sucking another cock. I've always loved anal play with women, licking, fingering and anal sex, absolutely love it all. I was very hesitant as I covered Randy's ass with the washcloth, I waited several minutes then filled my palm with shaving cream, removed the washcloth and began to lather Randy's ass. It was very odd feeling another man ass, especially when my fingers traced around his asshole, but as my finger kept running across it it seemed less and less odd plus the reaction from Randy every time I touched him was encouraging.

I began to shave Randy as he had done to me, spreading his cheeks to get between them as far as I could. Without my asking Randy moved to his knees, allowing his ass to spread wider. This also gave me access to his hard cock that was pointing straight towards the table. I was able to shave the entire area completely smooth, stroking him throughout the final shaving. Once complete, I wiped all the excess shaving cream and admired the work I had just done. As I looked at Randy's ass, completely smooth it didn't look much different than a woman, minus the cock and balls that were visible.

Following what Randy did, I poured some oil into my hands and began to massage all the area I had just shaved. Paying the most attention to his cock and balls, by this time I had another raging hard on, his cock felt amazing, so hard, so smooth. My other hand running along his balls and between his ass crack feeling his smooth asshole. I began to touch and massage around his hole, I felt him begin to press back as I held my finger in place, feeling his ass open letting my finger in easily. I continued to slowly finger his ass as I stroked his beautiful cock. Once I knew Randy was close I had him roll onto his back, immediately taking his cock in my mouth and moving my finger back into his ass. I took his cock easily down my throat, working up and down his entire length. Randy's moaning got louder and louder, his hips began to move forward, thrusting each time my mouth moved down on his cock. With in a few more seconds Randy was holding my head down on his cock as he exploded inside my mouth. I felt his cock throbbing as jet after jet of cum sprayed into my mouth swallowing every drop.

The ass play became a standard part of our play as did the mutual shaving every two or three weeks. Randy would often finger and lick my ass, occasionally he would use the prostate massager or some other toy on me as well. I really loved having my ass played with and really loved the toys, I loved the feeling of being stretched. One day after Randy shaved me he gave my ass a thorough licking as he always did, then he began to massage me with the oil, finger fucking my ass and stroking my cock. Then I felt a second finger, I moaned as Randy slowly and gently worked 2 of his fingers in my ass, I don't think any of the toys he had used were as big as his two fingers, once I relaxed it felt amazing.

After several minutes Randy instructed me to lay on the floor, he wanted to show mw a new massage technique he recently learned in a class he had taken. I laid down on a towel, Randy kneeled along side me and began to massage oil into my back, he poured more oil into the crack of my ass massaging my asshole and slipping his 2 fingers back inside me. Next I felt Randy swing a leg over my thighs, straddling me, using both hands on my ass he pushed upwards, spreading my ass then releasing, he did this several more times each time it felt as though he was spreading me open more and more. Next I felt Randy lean forward, nestling his cock between my ass cheeks and slowly sliding between them, I could feel the length of his entire cock glide along my asshole, I was shocked how intense the feeling was, I never in my life thought I'd be in this position and loving it.

Randy slid his cock along my ass for the next several minutes, adding more and more oil. As Randy slid his cock between my cheeks I began to really enjoy the feeling. I began to want to feel his cock inside me. I started moaning louder, pressing my ass against his cock, letting him know what I wanted. Without thinking I reached back grabbing Randy's cock and placing the head against my asshole, I felt him pushing forward, very slowly, I felt his head begin to enter me, the feeling was intense, not painful but pleasurable. I pushed back wanting more of his thick cock inside me, stretching me open, taking more and more inside me the pressure I was feeling eased as Randy was buried deep inside my ass. He slowly began to withdraw, then enter me again, this continued over and over, Randy was know fucking my ass, feeling his entire length slide in and out of me was incredible. As Randy's tempo increased I knew he was getting closer, I looked over and begged him to fuck me, I begged him to cum inside me, I wanted to feel him cum inside me. Randy grabbed my hips, lifting me to my knees, he began to drive his cock inside me, harder, deeper. "Fuck Randy cum inside me!" I repeated over and over. As I looked down I could see the cum dripping from my cock as Randy pounded me harder, then with a final thrust Randy buried deep, he held my hips tight as he began to fill my ass. I felt him throbbing, I knew he was pumping his cum deep inside me.

After Randy pulled his cock out reality set in, I was just fucked by another man! I had many many mixed feelings, but the overwhelming feeling was just how amazing it felt, sure there was embarrassment, I felt a little shame/guilt but felt all those when this bi exploration first started and I knew they would not last long. I went into the bathroom to clean up, my cock was still rock hard, cum still dripping from the head, Randy's cum dripping out of my ass, reaching back slipping a finger in my ass, feeling Randy's cum, fuck it was turning me on. I cleaned up, got dressed and went out and had a couple more beers before heading home.

When I got home I jumped in the shower cleaning myself thoroughly started dinner and waited for my wife to get home from work. She barely made it in the door and I was pouncing on her. I led her into the bedroom, stripped her down, literally ripping her shirt off, buttons flying everywhere. I laid her down and immediately went down on her devouring her sweet little pussy. Going down on her is one of my favorite things to do, she is so responsive, cum's multiple times and just tastes delicious. I ate her to several orgasms before stopping. We stopped for dinner, then relaxed on the couch with a few glasses of wine, touching, kissing and teasing for a few hours. We went back into the bedroom, Kelly immediately began sucking my cock, returning the favor from earlier. As she was between my legs I told her to play with my ass, its been a while since she has done this and typically its only when I ask. I handed her the lotion as I asked, she lubed her fingers and began to play with my ass as she continued sucking my cock. Her fingers are much smaller than Randy's and definitely smaller than his cock. As Kelly was fingering my ass I told her to use a second finger, she obliged and inserted a second finger, fucking my ass. This pushed me over the edge and I told her I was about to cum, she took my cock deep in her throat, driving her fingers deep in my ass as I began to flood her mouth with my cum. I pulled her up, kissing her, tasting my cum off her lips and tongue. I know she always loves when I do that. As we relaxed in bed Kelly asked "What has you so turned on today?"

Part of me wanted to tell her but I couldn't, I just said "Its been a while eince you played with mybass and I really wanted it."

"Well if that's the reaction I'm going to get from you, I will be sure to pay much more attention back there."

"I'm going to hold you to that." Was my reply.

For the next several days all I could do was replay my last meeting with Randy. The thought of his hard cock gliding between my cheeks, then the feeling of his cock sliding inside me, the first time a real cock entered me, everytime my mind went there I immediately would get hard.

By the time Randy and I met again, its all I was fantasizing about. I walked down to Randy's studio he had a beer waiting for me. We sat and bullshitted for a few minutes as we always did, his hand was rubbing my crotch, which had me hard in seconds. Before we got too far I told him I was going to take a quick shower. When I returned Randy was already laying on his massage table, naked and waiting.

I walked over, looking at Randy's limp cock, I reached out taking his cock in my hand, I leaned over taking the head between my lips. I moved my hand and slowly sucked his entire length in my mouth. Using only my mouth I began to work is cock, it immediately began to harden. I loved feeling his beautiful cock harden in my mouth, such a huge turn on knowing it was me doing this. I loved Randy's reaction to the way I sucked him, surprisingly I found it very empowering. Knowing his cock was hard because of me, his moans were because of what I was doing and finally knowing when he came it was going to be because of me.

I took my time sucking his cock, feeling his entire length slidung between my lips and taking him in my throat. Feeling his cock in my throat was such a turn on to me. The feeling is always amazing. I love opening my mouth, lowering my head letting the underside of his cock slide along my tongue. When I feel the head hit my throat it opens, allowing him deeper, once I have him in all the way I close my mouth, wrapping my lips around the base of his cock and sucking as I move up his shaft. I do this repeatedly, then I just keep my mouth wrapped around him, working up and down his shaft, letting him fuck my throat.

It's not long before Randy's moans increase, him telling me he is close to cumming. This makes me increase my tempo as I want his cum badly. Randy's hips begin to thrust meeting my down motion, trying to get more if his cock in my throat. When I feel his cock start to throb I know he is close, I pull back so just the head is in my mouth, I don't want his cum shooting directly down my throat, I want to taste every drop before swallowing. I feel his cum beging to shoot in my mouth, his first two shots are always so powerful literally hitting the back of my mouth and tongue with some force. I swallow them happily then begin sucking the head working out the remainder of his cum. Sometimes I feel I just cant get enough if his cum, its so fucking delicious.

Randy reaches over stroking my hard cock as I finish swallowing his last drops of cum and letting his cock slip from between my lips. He grips my cock, pulling me towards the head of the table, guiding my cock between his lips. After a few seconds I start fucking his mouth, sliding my cock down his throat.

Afrer a few more minutes Randy excused himself and said he'd be right back and went into the bathroom. He returned a few minutes later dressed in a short denim mini skirt, he leaned over his table showing he was also wearing a thong, I said "what is this all about?"

He said "I know you do not want to fuck a guy, so I thought maybe you'd fuck me if I was a good little girl." As he was saying thus he was walking towards me, oil in hand, reaching out and lubing my cock. "Please daddy, I want you to fuck me."

Randy kneeled infront if me, hiking the skirt up and pulled the thing to the side, his fingers massaging his snooth ass with the oil, begging me over and over "please fuck me daddy, fuck your little girl."

Before I knew what I was doing I was pressing the head of my cock into Randy's ass. Once the head was in the rest of my cock slid in easily, in a soft sultry voice Randy continued to beg ne to fuck him...or her, he kept referring to himself as "my little girl."

Randy knew of my roleplaying with women, he knew what it woukd take to get me to fuck him and it worked. As I fucked his ass I thought if him as a woman, just like he was acting. Which definitely made the whole experience more enjoyable for me. I pounder "her" little ass as sge begged me to fuck her harder. it wasn't long before I had to cum, I grabbed Randy's hips, pulling yer onto my cock as I plowed deeper into her. With a final thrust I buried my cock deep inside Randy, filling him with my cum.

After words I jumped in the shower, after showering I came out and we had a few more beers before I headed home. With a lot of this exploring I get some guilty feelings or feeling a little shame, this time was no different. over time I realized it's just sex. I couldn't deny it felt good too, quite honestly it didnt feel any different than a womans ass.

When ever we had anal after that it was always when he was completely smooth and dressed. Randy admitted later he enjoyed crossdressing and the feeling of being used. It turned out being a lot of fun and we kept it as part of our playtime.