Another New Boyfriend

I am a 46 year old crossdresser and travel often for work. I only started crossdressing again a couple years ago, but did it years ago and loved it. I can only crossdress when I'm traveling simce my wife doesn't know or would approve.

To describe me, I'm a bottom-only, sissy who only enjoys sex as a female. I love younger guys (18-21)! I completely act the part of a real woman, enjoy sex as a woman and do myself up as a woman 100% in every way. Let me tell you, this is hard work! From shaving, enemas (for sex), nails, eye brows, makeup, etc., it is not easy being a girl. I have learned how to do it well though and last year it really paid off when I met Aiden, an 18-year old college guy from Texas A&M.

I wrote about our first encounter. It was amazing! I still see him when I come to town. Although we've developed feelings for each other, we've agreed to just date. He has been open about dating another girl (a biological female) who he'd been dating before we met, which is completely fair and understandable.

As he explained, they have an agreement themselves to date other people and as of recently, he actually told her he was dating me. He said she was actually intrigued about it and not turned off. He said she wouldn't mind meeting me, but we haven't gotten that far yet.

Usually when I'm in town, we go out to one of a couple different gay bars, maybe see a movie (yes, I gave him a blow job in the theater once), out to eat, then back to my hotel and make love. It is amazing every time. I love time with him. He is wonderful.

Lately, however, I've been traveling to Seattle more. Last month, I got a reply to an ad I put out from another 18-year old college guy, named Kasey. Wow! He is soooooo cute. Blondish hair, cute smile, 6'2", 150, amazing abs, a tiny tat above his chest and a monster cock.

He is also bi and dates women too. He doesn't have a girlfriend now, but has a FWB that he meets up with often. I always like to compare and when I saw her pic, I was a bit jealous. She is very beautiful. I wouldn't think he'd be intetested in a crossdresser, but hey, to each their own.

After we chatted for a while and after seeing her pic, I did not think it would go anywhere, but we ended up chatting on the phone and he wanted to get together.

The hotel I stay at had upgraded me to a corner suite that overlooks the city. Funny enough, on one side, there are apartments. if you pull the curtains all the way open, everyone can see in. As you guessed it, I had every intention of leaving them open too.

When Kasey arrived, I knew i had to go get him since the elevators only operate with your room key, so I had a pair of capris and blue blouse with a cute pair of heeled sandles. Of course, I had a sexy bra and panties under.

The elevator stopped at a lower floor and two women in their 20s or 30s got on. I don't know if they realized i wasn't a woman, but they didn't seem to notice.

Once in the lobby, I saw Kasey. He smiled and came over. I put one hand on each shoulder, stood on my tippy toes, kissed him on the cheak and asked if he was ready to go up. He said "I'm excited and nervous". I was too.

Once we got to the floor, he was a gentleman and let me go first. I think it was also to check me out. As soon as we got into the room, he was stunned at the size. It had a guest bathroom, full dining table, living room with two couches and two chairs and a huge flat screen. The bedroom was in the corner and off that was a huge bathroom with stand-alone tub, huge shower and double vanity.

I had most of the lights on, as it was early night time and dark out. Of course, everyone from neighboring buildings could easily look in.

I asked him if he wanted to sit on the couch. My heart was racing. He looked so hot and smelled so good. He sat to my right as i sat to his left. As we sat, we made small talk about the room and his day. I asked him if I was what he expected. He said the pics on my profile helped, but that I was much more attractive in person.

After a few minutes of chit-chat, I put my hand on his leg, reached up and started kissing him. He was definitely shy, so I could tell I had to start it. Once we started kissing, he gently put his left hand beind my neck and pulled my left leg over his with his right hand and gently moved his hand up my leg to my butt. I was still fully dressed. As we kissed (btw he is a great kisser), I reached down with my left hand to feel his cock, which started to become hard.

I asked him if i could suck his cock. Without hesitation, he undid his pants and pulled them down with his underwear, almost as if he was quickly reacting to a command from a drill sergeant. lol. It was so cute. I pushed away the coffee table and assumed the position on my knees in front of him. In my mouth his cock went.

By far, this was the thickest cock I've ever had in me. He was long too, but that I wasn't worried about. I knew he'd be thick from his pic, so I had played with a butt plug I have all afternoon to relax me. It is thick too, but I usually only keep it in my "vagina", not move it in and out, so I wondered how well this would work. With Aiden's cock, it worked great because he wasn't as thick. As I sucked his cock and felt him get bigger and harder, I had only hoped this young stud would be gentle with me.

After sucking his cock for a while, I stood up and said I would be right back. He asked "Shouldn't we close the curtains?" "No." I said. I went to the bedroom, grabbed the lube and a towel and came back out. In our earlier conversations, I asked if he wanted to have sex bare. He was on the fence and said he would bring condoms in case, so I figured this was my time to convince him.

I set the lube and towel down and slowly started to unbutton my blouse. I pulled it off and thew it on the couch, then unbuttoned my capris, slowly turning around, then sliding them down as my butt pointed to him. I pulled them off, then kicked them aside with my sandles, spread my legs and looked back at him over my shoulder. My legs were super soft and shaved and I had on a cute dark blue low-cut demi bra with matching cheeky panties.

I said "Are you sure you want to wear a condom and not cum in me?" "No, I want to cum in you if it's ok" he responded. I turned around, grabbed the lube and towel, got back down on my knees as I gently ran my tongue up his cock, put it in my mouth and slowly went down as far as I could. He put his head back and moaned. As I came up, I opened the lube and began to stroke it on his cock, then stood up, reached between my legs and rubbed some in my pussy.

After drying my hands off with the towel, I threw it aside, placed my hands on his knees, then bent over and kissed him. He reached up, caressing my cheek and staring deep into my eyes with passion. "Are you ready to fuck me?" I asked. He nodded. I stood up, took off my panties, then placed my right knee on the couch next to him, grabbed the back of the couch and placed my left knee on his other side, adjusting so I was straddled over him.

I reached around and guided the head of his cock to the opening of my pussy, then worked the tip until i finally sat down. "OH FUCK!" I said as he penetrated me. I slowly sat all the way down in his lap. As I looked down, I saw the look of pleasure on this baby-faced 18-year old guy. He grabbed my hips as I began riding him. I thought he would hurt, but he actually felt really good. After a minute, I began going faster.

He kept looking at my face and into my eyes. I was in ecstasy as I was looking up and back down with my mouth open as I moaned from the pleasure of his stiff cock. I couldn't contain myself as I blurted out "FUCK ME!". When I eventually looked back down, I noticed him staring at me still, his mouth half open in amazement, as if I was the most beautiful girl he ever saw. I didn't have to say anything. I began kissing him, then we touched foreheads as we kept staring into each others' eyes.

I could tell he really liked me. He then said "I can't believe how pretty you are." Awe... my heart melted. I began tingling as I got wet. My clit began getting super hard. I know we just met, but is this guy seeing this as more than sex??? He is doing and saying all the right things and knows how to turn me on.

By this time, I was panting, mouth open and staring into Kaseys eyes. "Oh my gosh, baby, you are going to make me cum. Kiss me!" I said. As we kissed, I moved my left leg through the couch cushion and behind his back, then the right one so that both legs were wrapped behind him as I sat in his lap in the lotus position with his cock inside me. "Hold me" I said.

He had his strong arms wrapped around me, holding me in place with my arms over his shoulders and behind his back as we continued to kiss and stare at each other with the passion of two newly weds. I was getting close, but wanted him to go first. "Cum inside me" I whispered, then kissed him.

He tensed up a little more, then eventually moved his hands to my hips with a strong grip. I began to bite my lip as I looked at him with passion, awaiting his manliness to explode deep into my vaginal canal. My legs were shaking from gripping him hard and pulling my body deep onto his cock. He then said "I think I'm going to cum" as he moved faster, panting as much as I was. "Fill me up with your sperm, baby!" I said.

"UGHHHH!!!!" he screamed as he pulled my hips into him and thrusted with everything he had. He was cumming inside me. I could only jiggle a little bit, but then I came myself, cumming so much all over his washboard abs. Wow! He was amazing.

He was still panting afterwards as I smiled, looking down at him for a kiss. We slowly connected lips as I felt his tongue touch mine. We gently continued kissing as he held me in his lap, still fully inside me, as if we were a couple deep in love trying to make a baby.

As we stopped, I reached for the towel and begun wiping his stomach off. "I guess you enjoyed it too" he said. I responded "Oh yes, baby. You know how to work me. Now the trick is going to be trying to get off of you without cum leaking everywhere."

As i worked my way off of him, I stood up, putting the towel between my legs as i grabbed my panties. "I'll be right back. I need to grab a pad" I said. i hurried to the bathroom and realized my pad & tampon bag was still in my luggage. "Fuck!" I said as i could feel his load oozing out of my vagina. I ran to my bag, unzipped it and grabbed a pad. He could see me in the doorway and acted as though he was not trying to look, but I could tell he was. With my pad in place, I removed the towel and pulled up my panties.

I came out of the room and walked over to him. He already put his underwear back on, so i stradled him again and sat on his lap. "It's ok to stare at me. i'm not embarassed. I have maxipads and tampons for after sex. You boys cum a lot" I said as I laughed. He laughed too and we kissed more.

I had some wine and asked if he would open it. He said yes, so I brought it over along with two wine glasses and an opener. I went into the bedroom and grabbed a blue lace and satin flounce slip I brought and put it on. When I came out, he took one look and said "That is so sexy." "I hope it gets me a second round" I said.

I sat on the couch next to him as we enjoyed our wine. We both laughed wondering how many people in the next building saw us having sex. He ran his fingers through my hair and looked upon me with such affection and passion. He rarely stopped looking at me and was fasinated in me, asking me about my experiences as a crossdresser and what I like in a guy. I could tell he wasn't just here to fuck me and leave. He wanted more... and so did I.

A good hour or more went by as we started to kiss again. I could tell he was getting excited again, so I reached into his underwear and began stroking his cock. I then stopped kissing him, looked at him for a few seconds, then went down on him. I sucked his cock until he got really hard. He was more comfortable this time. As I stopped, I asked him if he thought he could carry me to the bedroom. I am 215 lbs and although he's taller than me, he was only 150 lbs. He was defined though and it has always been a desire to be held and carried by a guy. He said he would try.

We stood up as I reached up and locked my hands behind his neck. He reached down and grabbed my butt cheeks, so I lifted my legs behind his back. He had me with no problem. We kissed as we worked our way to the bedroom, where there were many more windows and surely a greater audience.

He gently bent over, lying me on the bed. He then pulled his shirt completely off. His shoulders were defined as was his chest muscle and abs. Any girl looking through the window at him with his hard cock would likely be amazed. I laid there on my back, legs spread looking up at him in awe. He reached down and began pulling my panties off. I could feel the stickiness of his cum as the maxipad pulled away from my skin.

"Do you mind grabbing the lube and another towel in the bathroom?" I asked. As he did, i moved up and adjusted a pillow under my head. He came back, applied lube on his cock, wiped off his hand, then got on the bed as he crawled towards me. My legs were spread as i began to tingle again in anticipation. He began kissing my stomach and slowly working up. I had goose bumps all over with my head laid back into the pillow.

When he got to my neck, I was so turned on that I started getting wet again. He wasn't even in me yet! He got up to me, with those beautiful brown eyes and kissed me. By this point, I looked forward to every kiss, as his touch was so gentle and his lips and tongue so luscious.

He stopped kissing me, grabbed a pillow and said "Lift up, honey". He placed the pillow under my butt and positioned closer to me. I pulled back on my legs with each hand as he pointed the head of his hard shaft to the opening of my vagina.

I looked right at his face as he gently slid himself into me. I let go of my legs and squeezed the bed sheets as I bit my lip in pleasure. As he worked himself further in me, he kept adjusting his legs so he was right where he needed to be. This isn't my favorite position, but I like it because the guy can go deep. In this situation, I actually was excited to do this position because I could kiss him and he was a bit longer than Aiden is, so I wanted to feel the difference.

He moved in and out of me, holding my legs back towards me, gently going deeper and deeper, all while looking at me. "You are amazingly beautiful. I could make love to you all night." he said. He started to work me harder. Ten or more minutes went by and he never lost his stamina. He just kept fucking me as I lay there and enjoy every thrust. He started to get more restless and positioned closer for leverage as his pace picked up. He slid my legs over his shoulders and pressed his body weight into me until my knees were close to my head.

Kasey was deep in me. His lust and desire for me was growing by every thrust. I couldn't believe how deep he was inside me. We kissed as he frantically worked his cock in and out of me like he was going for the Olympic gold. My hands were firmly on his cute tight butt cheeks as he worked me. I moved them up to his face, one hand on each side and said "Cum inside me, baby. I want you to shoot it deep and get me pregnant. Fill me up!" I said. After almost a minute later, he said "Here it cums, baby!" and shot his load deep inside me.

Kasey was out of breath and sweating. "Holy fuck I couldn't stop cumming" he said. I laid there a satisfied girl. Whooo that was amazing. This young stud knows how to please this girl!

As he slid himself out of me, I quickly got up and ran to my suitcase to change my pad. When I turned back around, Kasey was lying on the bed, still with a full erection trying to get his breath. "Hey now, if you stay like that, I'm gonna jump on you again" I said. "You can, but I'm gonna need a few minutes to catch my breath, girl". I laid down next to him, draping my leg over his as I rubbed his chest with my finger.

I said "For your age, you really know what you are doing in bed. You make me feel like you aren't just trying to get off, but that you see me and are making love to me. That turns me on more than anything". "I can tell you are really into me too, which is what I want. I'm pretty sure you can't fake an orgasm" he said. I laughed and said "No, especially with such a sweet and cute guy like you" I responded. I then kissed him.

We made love two more times that first night we met. We started to heat it up a little more for the potential voyeurs in the neighborly building as he fucked me doggie, cowgirl, reverse cowgirl and whatever else we can think of to give them a good show.

As the night went on, he opened up more to me. He felt more comfortable with me. It turns out he was in a relationship with a biological girl two years earlier who burned him. He was in love with her and she ripped his heart out for another guy who I'm sure she later regreted. Bitch. Kasey is so sweet to me and I couldn't imagine someone being like that to him.

Of course, Ive told him about Aiden and Aiden knows about him. They are both ok with it, as they are both dating other girls. Ive been back to Seattle two other times since, including now (where I'm writing this from) and Kasey and I have gotten together for some fun. Today, we went to the Fish Market, the first Starbucks cafe and had dinner before coming back to the hotel for drinks and an amazing night of sex. I'm not passable, but unless you're next to me or talking to me, it's not obvious. Regardless, neither him or Aiden have ever minded. This is one of the reasons my feelings for them run deep.

I am such a sore girl now. Kasey and I took a shower after sex and he is laying in bed passed out as he spends the night. I am writing this in the other room as I can still feel his spooge leaking out into my overnight pad. Oh, and "yes" for all those other girls reading this, get overnight pads when you're planning on going to sleep after sex. Believe me, the coverage is needed when you have a man who's young and full of cum! lol