Jack's First Time

There were no secrets between Jack and Marcy, hell when you have been married to the same person for almost 24 years and together for even longer there was no need.

Marcy had professed to Jack well before they were even a couple that she was bi and soon after they were dating Jack confessed he was a Crossdresser, a few years later he also said he thought he was at least bi-curious.

Fast forward some 20 years later and their sex life together was still good, but jack was still interested in a relationship with a man and his curiosity was growing every day. After some conversation with Marcy, it was agreed that Jack could find someone and explore theses fantasy's he was having.

After Jack had joined some online groups for local bisexual people he was met with a huge number of emails in his inbox, most just seemed way too rude and wanting to just jump right in to the sack, not exactly what was envisioned for his first time, then he found the email from Marcus.

Hello,

I recently saw your ad and just wanted to drop you a line. I myself have been with a couple of men over the years and would love to try it again sometime. My wife is also understanding of this and thinks its a great idea for me, plus I really love the fact that you are a Crossdresser. Hit me up if you want to chat sometime.

His message seemed really great and just what Jack was looking for. They passed a few emails back and forth and really seemed into each other. A coffee date was planned so they could meet and discuss what each other wanted out of the relationship.

Jack was always early when it came to meetings and he spent almost 20 minutes sitting in the coffee shop waiting wondering if every guy that walked through the door was Marcus. Right on time, he walked through the door. He was a taller man with a clean-shaven face and wearing a t-shirt and jeans, he was not overweight but for sure had what would be considered a dad bod. The back corner was free of any other people so they could discuss whatever they wanted without anyone hearing. Marcus explained how he had had a couple of experiences in the past, one before he met his wife and one year after he was married (With his wife's approval) and he was really wanting to try it out again. He explained how he loved his wife but there was such a rush when he was able to fuck another man in the ass, just something he could not explain. This was all fine with Jack as he had always envisioned himself as a total bottom, there for the pleasure of his man. It seemed like this situation would work out just great. Dates were set and there very first time together would be 2 weeks from now.

The Friday night before the first encounter, Jack's insides were filled with butterflies. Had been talking to Marcus pretty much every night since the coffee date and was asked it was cool that he would dress up for the first time, it didn't take much convincing to get Jack to agree. Marcus had mentioned that his wife would still be home when Jack got there so she could show him where he could change and set up space for his makeup.

Saturday morning rolled around and the butterflies had become a swarm of hornets in Jack's gut now but there was no way he was backing out of this. He had decided it was best to wait until the morning before going to have a shower and shave everything so he was smooth for Marcus. Marcy could see Jack pacing around the house and tried to reassure him the evening was going to go just fine and everything would be awesome.

It was finally time to leave and head over to Marcus's house, thankfully it was not a long drive because Jack could not really concentrate on the road thinking about what was going to happen tonight. After about a half-hour drive Jack was pulling into the driveway. The front door was opened even before Jack was able to ring the doorbell and he was greeted by a very chipper lady. Hi, I'm Candace, you must be Jack? Jack was able to at least replay with a Yes and Nice to meet you before he was ushered inside. Marcus is in the shower still Candace said, so I will show you the spare room where you can change and store your stuff.

The spare room was just off the master bedroom and was a very large comfy bed and it's own ensuite bathroom with shower, and best of all it had a full antique vanity, the kind jack had always wanted to put his makeup on. There should be lots of room for you to get all your makeup out here and get ready Candace said pointing to the vanity, and if you have lots of clothes to hang up you can use the closet.

Candace seemed like a very nice and understanding wife reminding Jack of his very own. Candace asked Jack you like a coffee to which he replied "Yes, Please"

Marcus was still in the shower as Jack and Candace sat down in the living room, Jack had never been in a situation like this before and was not really sure how to start the conversation off. It felt like forever of staring down into his coffee before he was able to start thinking of a cohesive sentence to say. "So how long have you and Marcus been married?" Seemed like a good start. Turn out Marcus and Candace had been married almost as long as Jack and Marcy.

Candace grabbed her purse and overnight bag and ran out the door, Jack was left sitting in the living room with his coffee all alone. It wasn't long until Marcus came back out of the bedroom wearing a t-shirt and some jeans. The guys talked for a few moments about what they both wanted to happen tonight, some rules, and what would happen if either one decided it was time to end the playing.

At this point, it was close to 1 and Marcus asked if Jack wanted to start to get dressed. Jack headed back to the guest room to get ready. He had packed only what he absolutely need for makeup to bring over and started to unpack it all on the vanity. His foundation, powder, and blush along with a single eyeshadow palette and a couple of different shades of lipstick depending on what eye look he was going to go for. He pulled out a short lace skirt from the bag and placed it on the bed to try and get out any wrinkles then got out his white silk blouse to hang up. He had decided on a very sexy red and black lace bra set with a matching garter to bring along, it was not the most revealing piece he had but he loved how he looked in this set. And last to come out of the bag was a brand new pair of thigh high stockings.

It didn't take Jack long to drop out of his street clothes and get into his bra and panties before he was able to sit himself down at the vanity. It was nice having an actual place to set all his makeup out, normally Jack has to just use the bathroom mirror which has no room at all to get things out. After about 20 minutes jack was fairly happy with how his makeup had turned out and finished up with a coat of coral pink lipstick. Jack had also brought some press on nails that he put on that were a matching color as his lipstick. He took one more look in the mirror looking from side to side before giving himself a kiss into the mirror before getting up to finish getting dressed. The skirt slid up Jack's stocking legs and sat nicely on his hips and his silk blouse buttoned up with just a few buttons undone at the top. A large hoop chain necklace highlighted his cleavage. The Wig went on and was adjusted and then time to slip into some heels. There was a full-length mirror in the corner and Jack could not help but prance around in front of it for a few minutes before it was time to head back out to the living room.

Back in the living room, Marcus was sitting on the couch watching some TV, He saw jack and motioned him over to sit beside him. "Wow", Marcus said looking up and down at Jack, "I don't really think I should call you Jack anymore, is there something else you would like?"

Jack had never really thought about a fem name before as he never left the house when dressed, he thought for a moment and said "How about Nicole?" Marcus looked up and down again and said Nicole was a great name. "Have a seat beside me" said Marcus as he motioned to the section of the couch beside him. Jack sat down right beside Marcus and promptly crossed his legs and leaned back into the couch. "Would you like to watch something special?" asked Marcus to which Jack replied "What do you have? Marcus flipped the TV over to a connected laptop and he already had a porn website loaded. "What would you like to watch," he asked as he was already scrolling down through the gay section. Right there near the top was one that caught Jack's eye, "BAREBACK BREEDING COMPILATION" and he pointed it out to Marcus.

As soon as the video started it was a super close up of a bottom getting fucked with slow, long pumps. You could hear the 2 guys moaning and it was already making Jack hard. With one last slow pump you could tell the top was cumming and then slowly pulled out to see a few pearls of cum drop onto the bottoms ass, then the closer up of the cum starting to leak out of the bottoms ass. Jack could feel his cock getting harder and pushing out on his panties as he watched. He tshen turned his attention back to Marcus who was just staring into Jack's eyes. "Is that what you would like to do, Nicole?" asked Marcus, Jack couldn't get any words out but was able to give an agreeing head shake.

Without saying another word Marcus reached down and started to unzip his pants and to Jack's surprise his half-hard cock popped right out, turns out Marcus was not even wearing underwear to make life a little easier. Jack had never been this close to another man's cock before but is looked like most he had seen in the porn. It was not huge (Which was good) but it was well defined and perfect looking cut cock with the mushroom head. Jack looked up at Marcus and he gave a glance letting know Jack it was okay to do what he wanted.

Jack reached out with his hand and wrapped his fingers around Marcus's still growing cock, it was a great experience seeing his own hand with his coral nails wrapped around another mans cock and was getting him even harder than the porn. He could tell he was already getting his panties slightly sticky. He could feel Marcus's cock expanding just by his hand being there and that gave him the push he needed to start exploring more. He gave a couple of long strokes all the way from the head down to the balls and cupped them a little before moving all the way back up to the tip again. He was taking care to pay attention to the tip. After a few more strokes Jack could clearly see Marcus was thoroughly enjoying himself as he was starting to leak pre-cum.

Jack moved a little closer before locking eyes with Marcus before moving his head down and kissing the tip of his cock. He could taste the salty pre-cum on his lips before he proceeded to part his red lips and encompass the whole head. Marcus's hand was instantly in the back of Jack's head as he worked the tip with his tongue before taking as much as he could in his mouth. It was a weird feeling at first, never having a cock in his mouth before this was totally alien to Jack but he did his best to try and find out what made Marcus feel the best. After a few seconds, he had the perfect rhythm with just enough twist on his neck to make Marcus push down with every bob of Jack's head.

Jack could feel Marcus lean over a bit and then felt his skirt being pulled up revealing his pantied ass, thigh highs, and garter. Marcus's hand was starting to move back and forth over Jack's ass going cheek to cheek with a little squeeze on each one before moving back to the other. Marcus leaned over and whispered to Jack "I thought you have never done this before?" Jack just made an agreeing sound not letting his lips off Marcus's cock.

After a few minutes of groping Jack's ass Marcus slid his hands under his panties so he could get some skin on skin contact. He slowly stuck a finger between Jack's ass cheeks at which point he said "Should we move to a more comfortable place to get more ready, Nicole?"

Jack shot off the couch and was standing up, there was a definite outline of his cock protruding from his skirt. Marcus grabbed Jack by the hand and lead him off to the guest bedroom, once inside the door he leads him to the bed and had him sit down before starting to unbutton Jack's blouse. At this point, Marcus's cock was right at Jack's mouth height and he could not resists taking it into his mouth again as Marcus was working.

The blouse was undone and pulled back over Jack's shoulders revealing the black and red lace bra. Jack pulled his arms back and let the blouse slide off his arms. As he looked up at Marcus and their eyes met Marcus pulled his cock out of Jacks' mouth leaned him back and forced him down onto the bed. Jack's legs were pulled up and his skirt was pulled down revealing his thigh highs, garter, and panties. Jack was always smart and wore his panties over top of his garter so the panties could be removed. After the skirt had hit the floor the panties were soon next. There as jacks fully erect cock sticking straight up at attention. Marcus removed his shirt and was now completely naked and looking at Jack with lust in his eyes.

Marcus got onto the bed and came close and whispered into Jack's ear "I think it's time to get your ass ready, get up on all fours". And with the command, Jack rolled over on the bed and proceeded to get up on his hands and legs with his ass in the air. Marcus got up off the bed and headed over to the nightstand, opened the drawer and pulled out a huge pump bottle of lube. He returned to the bed and sat down behind jack. Jack could feel hands caressing his ass cheeks and making large circles all over them, Slowly both sides were gripped and his cheeks were spread apart to reveal his tight little hole. Jack could hear the pump of the bottle and feel the coldness of the lube as it ran down from the top of his crack to his puckered little hole and a small shiver went through him.

It was only a second later and Jack started to feel Marcus's fingers rubbing up and down his crack passing over his pussy for a second every time, Jack buried his head into a pillow and let out a small moan and Marcus kept massaging. He was now circling Jack's little ass and paused right on top of it.

There was some pressure and jack could feel him trying to get a finger in. Jack leaned more into the pillow and relaxed and Marcus's finger slid right in. More moans into the pillow as Marcus was now slowly working in the lube by finger fucking Jack's ass. Jack could feel the finger being pulled almost out before being pushed back in. This went on for about 5 minutes before jack felt a second finger being placed in his ass, his moans were stifled as he faced into the pillow.

Jack could feel Marcus moving around on the bed and in a second he was right beside Jack's ear and whispered "Are you ready for this". Jack nodded in acceptance of the offer and Marcuse was gone again hopping back up onto the bed. He placed himself behind Jack. Jack could feel Marcus's hand's on either side of his ass holding him tight, then he could feel something warm and soft parting his cheeks again and planting itself right at jacks waiting ass. There was a small amount of pressure, then a bit more, and some more and within a second Marcus's cock head was just inside Jack's ass. Marcus took a slight break and just massaged Jack's ass cheeks while he waited for everything to adjust. "Are you okay?" asked Marcus to which Jack could only replay with a slight whimper and a head nod in agreeance.

There was some more slight pressure and jack could feel Marcus slipping right into his ass, with the amount of lube in there, once the head was in it was smooth. Marcus starting taking short thrusts at first but with each one he would slowly get deeper and deeper into Jack's ass until Jack could feel Marcus's balls lightly slapping against his ass.

Jack's moans were constant now as Marcus was slowly and deeply fucking his ass. He would quickly switch from shallow slow thrusts to full-on jackhammer mode to keep it feeling good. Turns out Marcus was great a finding what felt best for Jack as he could tell my the moans when he had hit just the right spot. After a few more minutes of pounding, Marcus pulled out and leaned down and asked Jack to roll over. When he rolled over Marcus had grabbed a couple of pillows to throw under Jack's ass to prop him up a bit. Once on the pillows, Marcus came back over and lifted Jack's legs in the air, and placed his cock head at Jack's ass again, and slowly slid it balls deep in one movement. Once he was all the way in he leaned over and said I want you to see my face when I cum in you.

At this point Jack really had no words left, just a head shake to the more experienced lover. Marcus started thrusting again, Being on his back was a whole new world of stimulation for Jack as now he could also grab his own cock but he only stoked a little as he was worried he would go too fast and be done before Marcus finished. He could tell Marcus was close as his pace and speed were changing and his grip on Jack's legs was tightening up. After a minute more of pumping, Marcus looked down at Jack and stated he was going to cum, Af few more thrusts and then he buried his rod as far as he could get in Jack's ass and let loose. Marcus made a few grunts while his cum was filling up Jack's ass.

Spent, Marcus leaned down and lay on top of Jack. Jack could still feel Marcus's cock in his ass but it was getting smaller and soon it popped out. At that point, Jack could now feel Marcus's hot cum trickling out from his ass and down his nuts. When Marcus moved off and laid down beside Jack and said "Let's make sure you finish too" before taking a finger again and rubbing his cum all over Jack's swollen ass and nuts. Jack started to stroke feverishly and within a few seconds was blowing his own load all over his stomach.

Jack laid his head back down on the bed and Marcus reached over with his hand and spread Jack's cum all over his stomach then reached down and gave Jacks now shrinking cock a few strokes. Marcus looked at Jack and asked, "Should we go have a shower?"