I was exploring my new life as a mid-thirties divorcee who recently relocated to a new state for work with few local connections. I have been bi-curious for many years but never dared to act. I would often navigate to trans porn websites. I eventually ventured to crossdresser and then to gay porn. I began to read free online ads to understand the dynamics of how to explore my fantasies.

One Saturday morning, I awoke with no weekend plans and found myself in online classified ads. One ad stood out. It described a 50-year-old-average male looking for an NSA regular partner since his previous hookup had moved.

I kept it open and finished masturbating to the fantasy of how the meeting would go. Later that evening, I reopened the ad with some liquid courage and replied, “Interested in exploring, never been with a man, but curious.” I proceeded to masturbate to videos of older and younger men. I went to bed with no reply in the inbox. I woke up Sunday and immediately logged in, there was a short reply inquiring what was I looking for.

This reply spurred deep thought and required coffee. I truthfully had not thought through what I wanted. I wanted to bottom, I wanted to top, I wanted to suck, I wanted to be sucked. I wanted to try it all. I couldn't answer what exactly did I want to try first? To say I was nervous was an understatement. I was determined to go through with the experience. I had to know.

Later in the morning, I returned to my computer and replied. I stated I was nervous and would require him to take the initiative. I knew what I wanted and I told him I was ready to meet and see. I reminded him this was my first time.

Instantly the reply came back with an address with an invite to come over now. I ran to the shower, cleaned up, and got dressed. I replied I was on my way. I was in a daze as I drove through town toward his neighborhood. I drove by the turn into the neighborhood twice, hesitating to take the final step. I finally pulled myself together and pulled into the driveway. Most of the neighbors' driveways were empty, so I assume most were out for Sunday morning activities. I got out, took a few deep breaths, then walked up the driveway and knocked on the door.

A taller man, roughly 6'2, opened the door. He was wearing a white Terry cloth bathrobe slightly open towards the top of his chest. He had thick chest hair protruding over the top and a slight gut. I caught myself wondering if he would be considered a bear. He smiled and invited me to step inside. I heard the door shut and immediately froze where I stood staring at his chest hair.

He broke the tension by extending his hand and introducing himself as Terry. He had a firm, but not overbearing handshake. I managed to make eye contact as we shook hands. His gaze was warm and calming. I followed him through the small hallway and into the living room. He offered me a beer which I eagerly accepted. He walked around the corner and returned with two beer cans. I thanked him, opened the beer, and took a hearty gulp.

Internally, I had butterflies galore as we stood there facing each other. He took a step back and untied the band on his robe and let it fall open revealing his full nude body. I looked down at his cock, it was average size and semi-hard. The hesitation and butterflies began to compete with horniness and desire.

I stared for what felt like minutes. He stepped closer, grabbed my hand, and put it on his chest. He guided my hand down his chest, past his stomach, then slowly down to his pubic mane. He removed his hand and without thought, I kept moving my hand down to his cock. I lightly grabbed the shaft, and a wave of emotions and the most intense sexual desire bubbled up. It felt warm, soft, and right. I explored his cock and balls with my hand as he slowly closed the gap between us. He grabbed my shirt and lifted it over my head which broke our body contact.

I had many thoughts going through my head. I didn't know if I should kiss him, put my hands back on his cock, or hug him. My indecisiveness froze me in place. He retook control by reaching over, unbuckling my belt, and button, and opening my shorts. He leaned in and took my nipple in his mouth while gripping and massaging my ass cheeks between my shorts and underwear. He slowly eased down my pants and kissed his way down my stomach. He slid off my underwear and my cock sprang free and hard. He took me in his mouth and began to suck slowly utilizing his tongue masterfully. I was easing towards ecstasy when he pulled back and helped me slip off my shoes, shorts, and underwear. He rose slowly, grabbed my hand, and led me down the hallway to a bedroom.

He stopped in front of the bed, turned around, and dropped his robe. He put his hands on my shoulders and pushed me downward. I reflexively bent my knees and found myself at eye level with his cock. It was now or never. I opened my mouth and put my lips around the head while licking his shaft. The feeling of a cock in my mouth was indescribable. I was cognizant of having a cock in my mouth while also feeling this could be a dream. I slid more of his cock in my mouth trying to take in as much as I could. I bobbed up and down a few times and felt his cock growing harder and longer. He began to moan reassuring me I was doing well.

He tapped me on the shoulder and said we could get more comfortable. He spun me around and told me to lay back on the bed. He crawled up from my feet and put my cock back in his mouth. He gave my cock a few licks and proceeded with the best blowjob I could have imagined. I was quickly approaching orgasm when he suddenly withdrew. He laid back on the bed and pulled himself face to face. He rubbed his cock on mine and began kissing my neck. We rubbed our cocks together while he continued to kiss my neck and ears.

I wanted to feel his cock back in my mouth. I reached down and grabbed it as we tried to change positions. We rolled over and I licked my way from his nipples down to his cock. I eagerly sucked his cock while my hands explored his balls. He spread his legs slightly. My fingers explored his balls and then down and around his hole. I kept sucking while rubbing his ass with my fingers. The realization this was a man's ass in my hand and cock in my mouth just increased all emotional and physical sensations. I began applying pressure to his hole with my fingers while increasing the tempo of bobbing up and down on his cock. I felt his cock grow in my mouth as he began moaning. I sucked quicker and pushed my finger harder. I could taste a saltiness permeate my mouth. He violently squirted in my mouth to the back of my throat. Stream after stream filled continued to fill my mouth and escaped down my chin. I caught as much as I could savoring the texture, taste, and smell. I instinctively swallowed while the flavors remained on my lips. It was not off-putting, and the aftertaste was quite stimulating.

He pulled me up and rolled over to again switch positions. He asked if I wanted to cum in his mouth or his ass. Without hesitation, I blurted out, “Your ass.”

He pulled back and retrieved lube and a condom from a drawer. He lubed his hole and told me to put on the condom. He then gave my covered cock a few licks then squeezed some lube and stroked my shaft. He got on all fours with his ass facing me. I positioned myself behind him and began to put my finger in his ass. It felt tight and warm. I added a second finger and slowly pulsed in and out.

I put my cock to his hole entrance and applied pressure. It was tight but well-lubed. I pushed until the head disappeared. The view was amazing. I watched my cock slowly enter his ass a little at a time. After a few more pushes and pauses, our balls touched. The sensation was overwhelming. I have done anal with several girlfriends in the past, but this experience felt different. The realization this was a man's ass was dominating my thoughts. I slowly began very short strokes with pauses between them. I increased to a rhythmic motion and he started pushing back against my thrusts. The condom was the only barrier preventing me from spraying my load quickly.

This was the horniest and most sexually fulfilling moment I had ever known. I heard his moaning as he pushed back in rhythm. It was less than two minutes before I felt the orgasm grow in my loins. I filled up the condom while still pumping his ass. It was a violently long orgasm draining my energy. I collapsed on the bed beside him as my hardness subsided. He lowered himself beside me and we both lay in silence breathing heavily.

He finally broke the silence. He explained he normally tops but wanted to ensure I went all the way through on my first time at a comfortable level. We both got dressed and returned to the living room. I finished my beer and agreed to come back in the morning.

I'll forego the range of emotions and thoughts on the drive home, but by the time I crawled into bed, I was already horny for the following morning. I awoke before my alarm. I quickly showered and drove over at our agreed time. He let me in wearing the same bathrobe and led me back to the bedroom.

I quickly undressed and sat on the side of the bed naked as he dropped his robe to the floor. He walked over and put his cock at eye level. I knew what to do. I took my time exploring his shaft and balls with my tongue and mouth while feeling his ass with my hands. He quickly grew hard. I took all I could in my mouth and bobbed up and down in short and long strokes, stopping short of gagging myself.

After a few minutes, he withdrew his cock and pushed me back on the bed. He grabbed the lube and a condom from the drawer then came back and gave my cock a nice suck. He spread my legs slightly and began rubbing around my hole. He put some lube on his finger and rubbed the outside. My ass was both resisting and inviting his finger. I felt slight pain and pressure as he broke the barrier. He continued to ease his finger in and out. After working my hole loose, he then stood up and put on the condom.

He told me to roll over on all fours with my ass facing him. I felt him crawl behind me and grab my hips to maneuver me into the proper angle. He stuck his finger in a few more times then I felt the pressure of something else. He lined up his cock and began to apply pressure. My hole slowly admitted his head with a pop. It hurt and he paused to let the pain subside. He continued to ease in bit by bit pausing a few seconds between pushes. He stopped when his hips were flush against my cheeks and waited a few moments. I tried to breathe and relax. Slowly, the pressure started to ease. He began with slow and short strokes. The feeling was indescribable. I felt full and stretched. The pain slowly transitioned to pleasure as I relaxed. He maintained a slow and gentle tempo while I adjusted to his girth.

After a few minutes, he withdrew and told me to roll over. He pulled my legs to my chest and lined up for the missionary position. He slowly pushed in. The feeling was different and more pleasurable. He pumped me while holding my legs to his shoulders. He then leaned in and moved my legs behind him while keeping his cock inserted. He leaned down and began to kiss me while continuing to pump. Instinctively, I kissed back.

The two new pleasures of being a bottom and kissing a man were enough to bring me into a new ecstasy. He continued to increase the length and speed of his strokes. The pleasure eventually overtook all the pain. I was in pure heaven. He then raised back up on his hands and continued to pump. He told me to jerk off while he increased the intensity. I began to stroke my cock in time with his strokes and became completely lost in pleasure. The orgasm started deep inside and fired out through my cock. Streams of cum squirted up to my chin and all over my chest. He moaned and filled up the condom while still deep in me. He collapsed back on my chest with his cock still inserted. We lay there recovering in ecstasy as his cock slowly subsided.

This could have been what happened had I responded to the ad. The first is yet to cum...