Letting My Boyfriend See It All

Throughout high school and college, I was extremely conscious about my small penis size. It fluctuates between one and four inches, depending on my mood, and whether or not I'm fantasizing about cuddling with a handsome man. If I were to have a few drinks, it tends to shrink even more. I've never masturbated by stroking my dick up and down like pornstars, but instead, I've always pinched the tip of my penis with both index fingers and thumbs and pulled back the skin to gently rub the underside of the tip until cum dribbled out onto my proportionately small balls. Size was something that had always brought feelings of embarrassment, and even today, it feels like a forced confession to write about it. As a teen, I hated doctor's visits and locker rooms and whenever I had to shower at a public Rec center or gym, I'd do so with swimming trunks on. I can hardly remember a time when I was not extremely conscious of how different I looked from other guys.

In college, I overcame unwanted peer pressures and decided to embrace my feminine side as a gay male. I can't remember exactly when I started wearing panties but it was probably around that time. What had failed to evolve over the years was my reluctance to expose my naked body, whether it was responding to a request from a Craigslist ad (that was the Grindr of the time) to send a photo of my naked self, or changing at the local 24-hour fitness. I just didn't like being naked in front of others.

When I lost my virginity to my first boyfriend at the age of 19, there was a huge burden lifted off my shoulders. The excruciating fear of being naked in front of a man I was attracted to, was dispelled in that moment. His name was Daniel Janowitz and I met him through Craigslist (that was the Grindr of the time) and from the very start, he found a way to make me feel comfortable in my own skin. When I gave him a blowjob on our first date, I was given the reassurance that I had the ability to arouse a man. Seeing Danny so erect for the first time brought a sense of reassurance and comfort in knowing that a man would be so aroused by my oral techniques. In hindsight, I don't think there was anything particularly special about it. I had only hoped that my mouth felt warm and arousing for Dan as I sucked on half of his eight inches as best as I could without being so obvious that it was my first time sucking dick. My lack of confidence in sex at the time might've been attributed to the fact that I was teased all throughout high school and really struggled with my sexuality. Dan was much older than my peers, who made my life difficult for being gay. He was 54 at the time, and while some might consider that unorthodox, I was simply attracted to him. All I've ever wanted in a significant other was a strong, sexy, faithful, sweet man who could treat me like his Asian sweetheart and Danny was that man.

Dan was the opposite of me. Experienced, large and strong, salt and pepper hairs covering his chest and stomach with broad, muscular shoulders. He weighed about 100 pounds more than me at the time and quite frankly, he was perfect. I loved the way he would kiss me and make love to me, and even today, I feel so fortunate to have lost my virginity to such a gentle, sensual, genuine man who was accepting of me. He asked me to be his official boyfriend after our fourth date and without hesitation I said yes.

It was after we became partners that I came clean to Dan about the reason for my shyness when it came to being naked in front of him. Yes, we went all the way on our first date and I knew he'd seen me bare down there, but I remember early on, I would try to make myself as erect as possible before we would make out to make my small size less noticeable.

It was an ordinary, cold rainy night in the Bay Area. We'd been dating for about a month and I went to Dan's apartment after my evening class to join him for dinner. I preferred doing my homework at his place anyways, as my dorm tended to get loud and distracting every week starting from about Thursday. We finished a light dinner and I lay my head on his lap as we both got comfortable on his couch. He put his hand in my shirt and started petting my abdomen with the backside of his hand. That's when I told him about my insecurities of being a small sized guy.

"Jamie, I think you're so attractive just the way you are," my baby reassured me.

"Thanks," I replied awkwardly. I wasn't sure what I was expecting or what his reaction would be but it felt nice to hear him say that.

"I want to see all of your beauty, Jamie. And I want to see my body connected to yours," Dan said, as he held me close. His hands began to massage my butt cheeks from outside of my jeans.

Not really knowing what to say, I looked up at Dan and he moved in for a kiss. It was as if I had said something to make him more aggressive, sexually. I closed my eyes and let his tongue gently part my lips and slither into my mouth. When our lips separated he asked me if I was OK with showing him "all of me". I looked at him straight in the eyes and saw a man I could trust and felt very safe in his embrace.

"Ok. I want you to see everything," I committed to him.

This time, I leaned into him for a kiss and he squeezed me even tighter into his masculine body. His manly hands unbuttoned my top and removed my shirt by gently stripping it off my shoulders. It was just chilly enough that my pink poofy nipples were hard and they felt more sensitive than usual. He didn't waste any time in continuing to remove my pants and my boxers.

"Oh my god. We're going to have sex again," was my only thought, although I tried to pretend like it was expected and familiar.

I was relieved to have not worn panties to class that day, as it was in college that I began to wear panties under my boy-jeans. On this day, I was wearing regular boxers and it was a relief. We were only a couple for a month, after all, and I didn't want him knowing that I often wore women's panties, for I just didn't want to ruin anything. I'd later learn that Danny loved femboys and by our one-year anniversary, I would have a closet full of girly clothes to wear for him in private.

There I stood, completely naked in front of a man I met on Craigslist only a month ago, yet feeling as confident as ever in my body as I had ever felt. It was a liberating feeling to have Dan check me out from head to toe, knowing he was getting turned on at the sight of my smooth, naked body. As intimidated as I was of Danny's eight inch cock bulging out of his shorts, I felt somewhat empowered to know that I dictated how hard it got in that moment.

"You're so hot, Jamie," Dan complimented me.

I felt my face blush a little and I didn't know what to say. He put both his hands on my hips and kept me at an arm's distance. I noticed my cock was still in its tiny-state.

"You don't mind that I'm not as big as other guys?" I asked Dan. Vulnerability and shyness began to take over my newfound confidence.

"You're perfect just the way you are cutie pie."

This was the first time he called me that. It would be a nickname he used for me over the next two and a half years.

Danny's compliment and his gaze was overwhelming and I could feel my heart beating faster and faster. I found myself wanting his embrace and I slowly moved closer to Dan until I was looking up at him and we were doing our tongue kiss again. His masculine, hairy arms wrapped securely around my buttocks and I could feel his hands spread my ass cheeks as the tip of his gentle fingers massaged my hole. I kissed him back with my tongue and closed my eyes to let him know I approved of what he was doing and wanted more. He seemed to understand.

"Let's go to the bedroom Jamie. I want to see all of you."

I didn't quite know what Dan meant by that, but I trusted him. Dan carried me into his bedroom and lay me on his king sized bed. I had a twin sized bed in my dorm so it was nice to sprawl out on so much space. His satin sheets felt like warm milk being poured over my hairless body. My cock was still only about an inch but I didn't care anymore. Dan stripped naked also and joined me on the bed. I was surprised to see that he was pretty hard already. I invited him to cuddle with me and he moved closer as I laid flat on my back.

"Show me how beautiful you are, Jamie,"Dan said to me as he put both his hands on the underside of my knees and lifted my thighs to my ribs. He gently spread my pale smooth thighs apart and continued to apply gentle pressure outward so that my legs were spread as wide as possible, knees bent and ankles in the air.

I'm a little bit on the thicker side and not as flexible, so it was a bit uncomfortable to be lying on my back with my knees being pinned down almost at my ears. My cock was 5-6 inches away from my chin and had my dick been a robust eight inches like Dan's I think I could've gave myself a blowjob. I glanced at Danny and saw that he was fixated on my crotch.

"Can you spread your pussy for me with your hands?" he asked me.

For the entire time that I dated Dan, he called my anus my pussy. It made me feel very feminine, but this might've been the first time he called it that. I knew what he meant. I instinctively put both hands on my butt cheeks and spread apart my ass so that Dan could see my opening and even some of my pink insides when I relaxed and took a slow breath out.

"That's it Jamie, show me everything," he instructed me, as I held my pose for him for as long as I could. I tried to relax my anus as much as I could so that he could see as far inside as possible.

I suddenly felt the familiar sensation of embarrassment and shame rush throughout my body as I tried to distract Danny's eyes away from my 1-inch penis by spreading my pussy open for him.

"I'm sorry it's really small," I said to him.

"Don't worry, Cutie pie, I think you're perfect just the way you are," he reassured me.

His words made me blush, as though my first crush had given me a compliment, and in that moment he pinned both my legs down to my chest and sunk his face into my pussy. I felt his tongue swirl in and out of my most sensitive areas and he was making all kinds of squishy sounds with his mouth. My hands were still in the same position, spreading my pussy wide open for Dan to kiss. As he put his tongue as far as possible into my opening, I could see that he was making me hard. I now had a full four inch erection.

"It sounds like you're eating a watermelon, Danny!" I teased my boyfriend for the sounds he was making.

"You taste better than a watermelon, cutie." Danny continued to slurp on my anus.

I had never imagined that a handsome man like Dan would ever enjoy eating me out like they did in the x-rated movies. Until a few weeks ago, I had never even kissed a man or woman, let alone given or received a blowjob. Yet, here I was with an attractive older man who was everything I'd ever dreamed of. He was gentle, courteous, sensual and thought my feminine body was attractive. I wasn't feeling uncomfortable or shy anymore. I was proud to let him see every inch of my body including my smooth cock which was now rock hard and bigger than I had ever seen it.

Danny soon transitioned from sticking his tongue in my hole to putting my cock in his mouth and it drove me absolutely wild. He bobbed up and down, still making the same slurping sounds as before. I could tell he was turned on too because his breathing was getting heavier as well and his fingers found its way into my wet pussy. He started to finger me while sucking my dick which made me moan uncontrollably.

"I'm about to explode Dan. Please. It feels so good."

I found the strength in between whimpers, moans and cries to let my man know he might expect some body fluids in his mouth soon.

Just as I warned him of my imminent orgasm, Dan pulled his finger out of my butt and crawled up the bed to snuggle right next to me. He always seemed to know when to slow down and it was a reminder that he was in control. I trusted him with all my heart and my body was yearning for more. His left arm was underneath my body, folded around my smooth armpit and his fingers interlocked with mine as I lay on his bed, in his arms, staring at his bearded handsome face. His right hand gently massaged my nipples and crawled down to my belly button, and eventually wrapped around my four inch erection.

He kissed me on my cheek and whispered into my ear, as if there were other people in the room.

"I want to see all of you Jamie. I want to see your pretty face when you squirt for me."

I had no idea what I looked like when I had orgasms but I had nothing to hide from Dan. He had just seen places on my body that nobody in the world had been exposed to and I wanted to share more with him.

I glanced over at Danny who was only inches away from my face and I could see that he had a loving gaze that fixated on my eyes. He began to stroke my cock. Of course this sensation was new to me because I never masturbated that way. I never even thought stroking my cock was possible because it was so small but Danny was proving me wrong. Every now and then I could feel his rock hard, manly erection press against my hips. I was happy to see he was aroused, too. His hand was large enough to envelope my penis and when I looked down, it just looked like he was making a fist below my tummy. Danny never said a word and his eyes stayed fixated on mine as he brought me closer and closer to orgasm. I squirmed around but his other arm held me firmly in place, hand still interlocked with mine. I could feel my palms getting sweaty but I couldn't move or get out of his strong, loving hold. My moans turned to whimpers and cries and I turned to Dan and tried my best to speak.

"Ah, Ow, awwww I'm gonna cum babyyy"

My mind went blank and I lost control of my body. In a half-conscious state I looked at Dan and he was still staring into my eyes with the same stoic expression. I knew I was making crying faces as I was shooting cum into his hand but I didn't care at that point. His palm was big enough to catch all of my love juices and not let any of it leak onto his bed. I lay there, twitching and squirming around but he held me close to his body and prevented my hips from going into a spasm.

He got up for a brief second and walked to the sink in his bedroom to wash his hands. I looked down at my body and there was no cum anywhere so he must've caught it all in his hand. There was a little bottle of lube that he used before fingering me. I remember feeling a little cold and wanting to feel the warmth of Dan's embrace. He crawled back into bed and this time, parted my legs and got on top of me. His upper body was supported by his elbows, pinned next to my ears and I hugged his wide, hairy back. I wrapped my legs around his lower back and I felt his warm hard penis at the opening of my pussy. He didn't have a condom on like the first few times we had sex but I trusted Dan at this point and didn't feel the need for one. Once he asked me to be his boyfriend, I decided that it was ok to take the next step together and do it without a condom. His cock felt warm and slippery but firm and I relaxed as much as I could to take him in. He kissed me on the lips to distract me from the initial pain and I hugged him as tight as I could. As his large 7 inch cock slowly entered my body, I felt a rush of emotions and started getting teary eyed. I continued to hug my Danny who was now completely inside of me, slowly pumping in and out.

"It feels so good it makes me cry. I don't want you to see me crying," I told him.

Danny got back on his elbows and wiped my tears with his thumbs.

"I want to see all of you Jamie. I want to see your pretty face when I'm inside you."

It was that moment where I just started all-out sobbing but my eyes must've communicated how much love and passion I was feeling.

"Thank you Danny for being my first," I just told him what honestly came to my mind in that moment. It wasn't our first time, but he was my first boyfriend and I was so grateful for everything he had done for me in my development as a gay man.

Danny just locked eyes with me and pumped in and out of my body. We kissed the rest of the way. Our tongues teased each other's but mostly my focus was on my pussy. I tried to appreciate the sensation of being connected, physically and emotionally to my boyfriend. Our hands were interlocked and every time Dan's cock would push into my tummy it felt like air was being pumped into my stomach, causing me to breathe hard into Danny's mouth. Dan stuck his tongue all the way in my mouth and released a loud groan. I didn't realize he came until he hugged me close and thanked me also for being his boyfriend.

"I want you inside me forever," I flirted with him, still breathing heavy from having sex.

Danny just hugged me and I knew I never had to be embarrassed in front of him ever again. We had a two and a half year relationship after that and grew really close. He helped me so much with my confidence as a feminine male. For my 21st birthday Dan and I even went to Las Vegas and I wore a (yellow) bikini in a LGBTQ-friendly pool party, which was something I thought I would never be able to do. I've had about a dozen different boyfriends after him, but I've thought of him from time to time and I would be lying if I said I didn't think of him during sex with other men these days.