My First Night with Ed

I've always known I'm bisexual. As I entered puberty and sexual thoughts became more prominent, my search history would confirm that I had as many thoughts about naked men as I did women. Surprisingly though, my sexual interest in men always has gravitated towards older men, silver foxes or silver daddies as they might be called.

My sexual experience has always been with older men, from my first encounter when I was 18 to this Friday night as 23 year old me types out a personal ad on the m4m section of craig's list looking for a submissive older man interested in regular 'daddy-son' role play, although tonight I'm mainly interested in getting my dick sucked a couple times. I'm new to the city, having moved here a couple months ago after finishing college, and I've had little time to make any meaningful connections yet.

As replies start to roll in, my pickiness in men becomes apparent. This guy is too hairy, this one doesn't have any body hair, that picture is too gross to seriously consider, this guy can't type a complete sentence...I like a confident guy, ironic since I tend to play the dominant role sexually with other men.

I don't have much success with my ad, the few emails I do respond to don't get a response back from the sender, and I settle into a session of prolonged edging that produces an incredible orgasm that I shoot all over my chest and stomach, scooping up the come and eating it as I would have for the daddy I never found tonight.

I shower, change and start to get ready for bed when my phone alerts me to a new email, another reply to my ad. I open the message as I turn on my electric tooth brush, and read through the thoughtful and respectful response:

Hi. I read your ad earlier and sat on the decision to write you or not, but it's been in my thoughts ever since so I thought it would be best to drop you a reply in case I am the 'daddy' you are looking for.

I am a 56 year old MWM looking for a special younger man with whom I can develop a long-term intimate relationship. My wife is aware of my needs, and has been encouraging in my pursuit. Given my professional status -- and detail to personal health -- I am looking to build a solid, trusting relationship with one man who I can be open with personally and sexually. I'm looking for more of a switch-style relationship though, so if you're looking for a total bottom that wouldn't work for me. Although I do love the idea of you calling me 'daddy' while I suck your cock, that turns me on very much.

I attached a couple of photos of me, I hope you understand not wanting to show my face until we know each other a little better for my own safety. To fill things out for you, I have a full head of white hair, blue eyes and am clean shaven.

I hope to hear from you,

Ed.

My cock twitched a little bit reading Ed's email, and I spit out the toothpaste in my mouth and started to rinse while opening the attachments he sent. The first was a heavily cropped photo of him in a tux with what must be his wife cropped out of the photo next to him. I couldn't get much from this other than she's taller than him, but maybe that's the heels, too?

The second photo was a delight, a full nose-to-toe nude photo, him standing off to the side but turned to the camera so you can clearly see his big, wide smile and the fullness of his magnificent cock. It wasn't enormous, it was both shorter and thinner than mine, but it was well proportioned to his body, stayed mostly straight off his body and had a delicious looking mushroom head that noticeably expanded past his shaft girth. I wanted to run my hands along it, and I gave my own cock a squeeze through my shorts.

I quickly fired off a response, thanking him for the thoughtful message, stressing how it is such a change from the other responses I received. I was into Ed from his first email, and I wanted him to feel special so he'd write me back. I complimented him on his body, acknowledging how hard he must work to stay in such good shape, and how hard looking at his cock had made me. I removed all pretenses and sent him back a full nude photo of me, sprawled out on my bed with my nearly 8" thick cock splayed over my stomach almost reaching my belly button.

I killed time a bit, just hoping he'd write me back, and after about 20 minutes I disconnected for the night. I woke up the next day to an email from Ed:

Tom,

Thanks for the kind response I really enjoyed reading your email. And your photo...wow!! I wish I had woken up to you in my bed this morning, I would have happily taken care of that big cock for you. Do you have any plans today?

Ed.

I was so excited to read his message, I couldn't type out a response fast enough. I had some plans with friends to visit the farmer's market and neighborhood book fair in the afternoon, but I'd love to meet up with him afterwards if that's what he was thinking.

He was putting in a few hours at the office, but we made plans to meet at a very swanky bar at 6pm.

I spent most of the day trying to distract my mind from my date that night, doing everything I could to not masturbate and save it all for Ed. I went to the zoo in the late morning before meeting up with my friends to walk around the remains of the farmer's market, then grabbing a quick lunch before walking around the book fair. It turned into a long day, and I didn't get back to my apartment until after 5, not leaving much time to shower, change and make it to the bar on time.

The bar was a 15-minute cab ride from my apartment and given my indecision over the exact perfect button-down and jeans combo to wear, I arrived about 10 minutes late. I emailed him in the car that I would be late, but didn't expect he would have read it and was nervous he would have left already. I hesitated a bit before going in because I didn't know what Ed looked like; I included my face in the nude I sent him the night before, but he didn't share any with me. Which, for the first time, got me thinking about the possibility I wouldn't find him physically attractive.

I was lost in thought when I registered someone was shouting at me, "What can I do you for?" the bartender was asking me, sizing me up, acknowledging I wasn't the usual clientele for this bar.

"I'm meeting someone here at 6" I said, scanning the dark, wood-paneled bar and the few patrons who were there. The bar stretched nearly the entire length of the room, open on both sides for patrons, with a row of highbacked booths on the right side and an elevated seating area above that.

Scanning the three guys at the bar, I didn't think any of them were Ed, and communicated that he wasn't there yet when a white-haired man popped his head from one of the booths and gave me a giant smile before standing up and walking over to greet me. We locked eyes, and any fear of physically attraction went away as I broke out in a broad smile. I closed the space between us and he engulfed me in a full hug and led the way back over to his booth. He told the bartender -- Charlie -- he wanted another old fashioned and asked me what I wanted to order. Unsure of myself, and wanting to appear more sophisticated than a guy who just order a beer in a bar like this -- I asked him to make it two and settled into the booth opposite Ed.

I apologized profusely for being late, but he told me not to worry about. He had gotten my email and had even emailed me back; I didn't check my email again and didn't get his reply. He told me that he was also running late, but his nearly empty drink told me that probably wasn't correct, he was just being polite.

Confidence and maturity exuded from Ed, and he immediately jumped into a series of very direct, very personal questions about myself, my life, and my previous relationships. He took sips from his existing drink as I answered each in more depth than was necessary, my nerves and the sexual tension was making me talk a lot more, and faster, than I normally would. I thought he was very handsome and sometimes had trouble holding his intense gaze, but he kept a warm smile on my face and nodded along

and asked follow-up questions as I went. I was starting a description of my first sexual encounter with another man as Charlie brought over our drinks. I brought the dark brown liquid to my lips and did everything I could not to spit it out, not to make a face that Ed would think is immature.

"You don't have to drink that" he said to me, laughing to himself a little bit.

"No, it's good" I managed to stammer out in a half-cough. And to show him my commitment, I took another sip of the hideous drink and set it down to continue my story.

When Charlie came back for another round, Ed noticed my barely touched old fashioned and confirmed it would be ok if I ordered something simpler like a beer, I didn't need to impress anyone tonight. Charlie ran through the tap list and I chose an IPA from a local microbrewery I'd never heard of before as Ed reached across the table to grab, and then down, my previous drink.

We stayed in the bar chatting for over two hours, Ed taking in two additional old fashions while I slightly outpaced him for beers, our conversation staying active and engaging throughout. He told me about his life as well, his wife and their family. How they started exploring more sexually after their kids went to college, Ed confessing his sexual interests in men and her encouragement in his exploration while she explored her own interests. After downing his fifth drink with me, he alerted me to the fact he needed to pee and got up from the table, stopping at the bar for a quick chat with Charlie on the way. Activity in the bar had picked up noticeably since we arrived, with most of the bar area filling up with a well-dressed, older clientele either waiting for their table to be called or making the first of many stops of the night.

I saw Ed walking along the far side of the bar, stopping to chat with Charlie again and obviously closing his tab. My eyes followed him as he came around the side of the bar and back to our table, reaching out for the coat on the bench hook I hadn't noticed before. He leaned down and asked me simply, "Do you want to head back to my place now?" and I couldn't get out of the booth fast enough.

Outside the bar, he easily hailed a taxi for us and followed me into the backseat. He pushed in right next to me, almost sitting on top of me, and after exchanging his address with the driver, he reached across my right leg with his left hand and started groping my hardon through my jeans.

"Mmm" he leaned over and whispered into my ear, the intoxicating scent of his cologne and whiskey-breath filling my senses, "you're so hard for me" he continued, fondling me more aggressively.

"Fuck, your hand feels incredible, I'm so horny for you" I whispered back, although apparently loud enough for the cab driver to hear as I saw his eyes flash into mine through the rearview mirror. I held his gaze and continued, "I wish you could suck me off right here in this cab" and slouched down a bit so he could rub more of my crotch.

The cab ride was short -- maybe 5 minutes total -- and I was completely hard and turned on upon exiting. Ed paid the driver and led me into his condo building, past the desk watchman he addressed by name and onto the elevator and up to his condo on the 39th floor. He maintained a respectful distance from me on the elevator and as we walked the short distance to his front door. But after leading me into his condo and asking me to remove my shoes, a switch inside him flipped and he instantly grabbed my body into his and pushed his lips onto mine, prying them open with his tongue which I met with an enthusiastic response. He pinned me against the wall as he continued his aggressive kiss, then broke it off just as unexpectedly and started walking down the hallway to the main section of the condo.

Which was absolutely fucking gorgeous! His condo offered more than a 180 degree view of the city and lake; later he told me that he and his wife bought and renovated three apartments to make their condo and owned most of the floor as a result. I was taken aback by the view -- accentuated by the low lighting in the room -- and was staring south out his windows when I saw his reflection approaching me with a drink in each hand. He offered me a beer while taking his whisky over to the coffee table and plopping down on the couch, looking at me lustily.

He leaned forward to grab his drink, and I caught his eyes as he returned to his seated position. Setting down my own drink, I started to slowly unbutton my shirt, one button at a time, exposing my bare chest and stomach more with each motion downward. I removed my shirt and set it on the floor behind me before aggressively pulling my belt open, then the button of my jeans before turning around and slowly peeling my jeans down my legs. I looked down at my protruding cock, a large, noticeable stain of pre-come on my boxer briefs. Then I turned around and put my arms behind my back, exposing myself to Ed's gaze.

He took me in, slowly sipping his drink, not saying anything but eyeing my up and down at length. I made no motion to go towards him, and after a minute or two of his gawking, he set his drink down on the table and stood up, closing the distance between us quickly. He reached with his right hand and cupped then squeezed my hard cock causing me to groan in lust.

"I love how you just took off all your clothes for me" he said, 'but I need to see the whole package" and he sat down on the coffee table, reached into my boxer briefs, and pulled them down over my large, hard cock in one quick motion.

"Oh, look at the surprise you have for daddy. My little boy has such a big surprise, is this all for daddy" he said to my cock, taking the base of it in his left hand and squeezing hard, causing a drop of pre-come to stream out of my cock head. He reached out with his tongue and caught the droplet, then swirled his tongue over my slit in a couple fluid passes that brought more and more of my cock head into his mouth before he fully engulfed it along with the top inch or two of my shaft, his tongue feverishly working itself over my cockhead and along the sensitive underside.

I was so turned on at this point, I raised myself on my toes and moaned loudly as I brought my right hand to the back of his head to encourage his oral exploration of my cock, his left hand pumping in rhythm with his mouth. My moans were met with loud slurping sounds and even moans from his own mouth as Ed continued to worship my cock with his mouth. I was struggling to hold off my orgasm, and he wasn't slowing down his pace at any rate.

I think Ed could sense I was close because he took me out of his mouth with a loud plop sound and ran his ran his hand from root to tip, using his saliva as lubricant. "I want you to shoot your load down my mouth and daddy will do his best to catch all of it, ok sweetie" he informed me as he took me back into his mouth.

"Oh god daddy," I replied in an excited state, "I just want to be a good boy and come for you. I want to be daddy's good little boy" I continued as he quickened his pace and brought me to the brink of orgasm. I was lost in lust and excitement and couldn't produce any discernable words in the groans and shouts of ecstasy I created as I pumped my large load down his waiting throat, three, four, five giant pumps from my cock as Ed tightened his grip around my head and accepted it all into his mouth without spilling any.

He kissed my flat stomach a couple of times before returning to my cock and cleaning off the remains of the orgasm. He took me out of his mouth but continued to jack off my sensitive, but still hard, cock as he looked up at me and smiled.

"Your cock is magnificent" he said, "let's go see what more we can do with this thing," as he stood up and led me by my cock down the hallway into his bedroom. It, too, featured a wall-to-wall view of the city and was nicely furnished with a large king-sized bed and several chairs and couch in a seating area off to the side.

I started working at the buttons on Ed's shirt now, reaching in to run my hands along his white chest hair and squeeze his nipples between my fingers while he worked the bottom buttons off himself. I leaned in for a kiss as he removed his shirt, tasting the remnants of my come on his mouth and the faintest hints of liquor still on his breath. Still engaged in our kiss, I reached my right hand out and grasped his cock for the first time through the fabric of his slacks. I couldn't get my hands to his belt buckle fast enough, and was soon fidgeting with the button of his slacks that I just couldn't get undone.

Ed stepped back away from me and worked the button of his slacks open and unzipped his pants showing off a patch of white pubic hair and the knowledge he had on no underwear. He stepped back towards me and leaned his head in to take my left nipple into his mouth as I reached my hands out and shifted his pants off his hips, leaving them dangling around his thighs but below his now exposed cock which I grasped in both of my hands, causing him to moan into my chest. I started pumping his cock in between my two hands as he continued to moan loudly and brought his lips back to mine.

I broke the kiss to tell him how much I loved having his cock in my hands, which caused him to moan even louder. I kept pumping him with my left hand and brought my right how down to cup his tight ballsack. I held them in my palm and pressed the tips of my fingers towards his perineum while using just the thumb on my left hand to tease his sensitive cock head. He was leaking precome aggressively which I used to coat my thumb as I continues its dance along his cockhead and sensitive underside.

"You ready, daddy" I asked in a playful tone and slide to my knees without waiting for him to respond. I helped him remove his slacks before taking his cockhead and about half his length into my mouth in one motion. He jumped as I put his cock into my mouth and instantly started grabbing at my shoulders, asking me to stop. I was a little disappointed when he exited my mouth, but he staggered over to the end of the bed and sat down, opening his legs wide for me before motioning me back over into my kneeling position where I quickly resumed my blowjob.

Ed's cock was almost perfectly sculpted for my mouth. It was less than 6" long and not very thick, so I had no problems taking almost all of him into my throat which his twitching cock told me he enjoyed. But I loved how his helmet was fatter than the shaft, and loved tracing my tongue over, sticking out the tip to trace under it and then taking long, flat licks from root to tip while continuing to smear precome over his sensitive cockhead with my thumb.

Ed was holding onto the comforter tightly with both hands as I brought him closer and closer to orgasm, easing off as I felt him grow more, keeping him hard and excited for me. Finally, he admitted that, "daddy needs to come" and I quickly brought him over the edge, removing my mouth off his cock as I felt the initial pumps of his come hit my throat and stroked him to completion, watching multiple eruptions from his cock as he flung his back onto the bed and fucked my hand with his cock.

Once he was done, left nearly breathless on the bed, I started scooping up globs of his come with my fingers and feeding it into his hungry mouth. He sucked my fingers clean each time I fed him, then rubbed the remnants into his stomach as his breath finally started returning to normal. I stroked my own hard cock a couple times and then left the bedroom and headed back down the hallway to the living room to collect our drinks, returning down the hallway with my hard cock swinging left to right as Ed has adjusted his position and was now laying on his side watching me come down the hallway.