Like many cross-dressers I’ve been sentenced to a life of secrecy. Over the years I have accumulated a small stash of panties, bras, shorts, slacks, blouses, stockings, and shoes. I wear them on the too little opportunities where I can sneak away without suspicion, mostly to the trusty adult bookstore. It is such a thrill to walk around in a semi-public area dressed like a woman and, sometimes, being pursued as a woman. I’ve had both oral and anal sex several times with men when dressed as a woman at the bookstore. However, recently I’ve been yearning for more quality and time when dressed.
Recently, I took up saltwater fishing, first, going out on fishing boats, and then fishing off the shore during our summer vacations. We rent a house two or three times a season. I like the whole fishing environment. The people are friendly, the ocean breeze always feels good, and it’s quite relaxing. One day when I was fishing I was talking to another angler. He told me about a large fish he caught the night before. I didn’t realize the beaches were open to night fishing. He suggested I try it sometime.
That night, I took my surf pole, fishing gear, and a chair down to the beach. It was beautiful and quiet. I could see an occasional person fishing or just walking along. There was only a quarter moon, so it was dark. I couldn’t distinguish a person’s features unless they were twenty or thirty feet from me. I thought to myself, I could be buck naked and no one would be able to tell unless they walked right up to me. With that, I took off my swim trunks, leaving on my long shirt that came down to the top of my thighs. Dressed in only the shirt, I picked up my surf pole, walked down to the water, and cast my rig into the surf. Then, I walked back to my chair, put my pole in the sand stakeholder, and sat down. What a thrill.
The few people that walked past me that night saw my fishing pole and walked behind my chair to avoid my line. I was sure that no one knew or suspected I was naked from the waist down. It was a beautiful night.
The next day I went to the local beach shop to get some suntan lotion. While I was looking around I saw the ladies bathing suits. I was getting excited thinking how sexy it would feel to be wearing one of them. Suddenly, I got a great idea. I picked out a skimpy black two-piece string bikini. Then, I looked around the shop a little more and found a pair of short shorts and a long shirt with “You know what I want” printed on the front. I almost forgot to get the suntan lotion.
I stuffed the items under the back seat of the car and drove back to the rental house. My wife was waiting for the suntan lotion so she could lie out on the front deck upstairs. When she asked what I was going to do today, I told her I was going to relax in the sun with her and go fishing tonight. She thought that was a good idea since she wanted to have a few drinks with the woman next door.
As the sun went down, my excitement went up. I put my surf pole, fishing box, bucket, chair, and carry bag with wine coolers in the car telling my wife I would be back sometime after midnight. I drove to the parking area near the beach where I pulled my new stash from under the back seat. Since there were only a few cars in the parking area and it was pitch black, I decided to change next to the car. I slid down my loose-fitting shorts and pulled on the bikini bottoms. Oh how good they felt. Then, I pulled on the short shorts. I was in heaven. I pulled off my shirt and put on the bikini bra before putting on the long shirt.
I looked around the parking area to be sure I was alone before grabbing my stuff and walking to the beach. Just as the night before, there were only a few shadows along the beach. I found a quiet spot near a lifeguard stand and set-up my chair. Then, I took my fishing pole and waded into the water, casting into the surf, before walking it back to the beach, setting it into the pole holder.
I felt so sexy walking around in a tight bikini. I walked back to the water and milled around knee-deep, enjoying the wonderful feeling. As I was standing there, I noticed a shadow walking toward me, so I walked back and sat in my chair. A man walked up to me asking, “How’s the fishing tonight?”
I replied, “I don’t know, I just got here a few minutes ago.”
He responded, “Would you mind a little company for a few minutes?”
I wasn’t expecting this. It was dark and I didn’t think he could tell what I was wearing. I didn’t want to send up a red flag, so I told him,” Sure, would you like a wine cooler?”
As he opened his chair and sat, he said, “Thank you that would be nice.”
I leaned over and took two bottles from my little carry bag, handing him one and opening the other for myself. He said his name was Dan and I told him my name was Gene (not my real name). We talked for a few minutes when Dan asked me how I knew when there was a fish on my line. I told him the rod would bend quite a bit.
“Like it is right now?”
I looked and saw it was bent like a pretzel. Without thinking I jumped up and grabbed the pole. It was pulling hard, taking me several minutes to wind it in. As I pulled the line onto the shore I could see a decent-sized flounder. When I bent over to pick it up, Dan said, “Wow, nice. And the fish isn’t bad either.” I suddenly realized what he was talking about.
After getting over my initial shock, I turned and smiled saying, “Thank you.”
I took the fish off the line and put it in the bucket. As I stood back up I backed into Dan. He put his hands on my hips. I could feel his cock against my ass.
“How does that feel?” he asked.
I put my hands on top of his. “It feels good.”
He nibbled on my neck a little, moving his hands up and around my chest. I leaned my head back and to one side giving him better access to my neck. My whole body was full of goosebumps. Again, I put my hands on top of his while he continued to plant small kisses on my neck. He was driving me wild.
He pushed his cock tight against my ass as he whispered, “Would you like some of this?”
I let out a little whimper, “Oh yes, I’d love some of that.”
He took my hand and led me to the lifeguard stand prompting me to climb up into it. He stood behind me with his hands on my ass pushing me up. Once in the perch, I sat down on the bench. He climbed up after me. Then he stood in front of me and pulled his shorts down revealing a beautiful seven or eight-inch cock. I reached it with both of my hands pulling him closer to me before taking a little lick of precum from his slit.
I began exploring the tip of his dick with my tongue. It seemed much bigger than others I have had in my mouth. It was also continuing to grow and harden. I closed my lips on it while still moving my tongue around the tip causing him to shudder. He put both of his hands on the upper back of my head prompting me to take more into my mouth. His large shaft slid through my lips and along my tongue. I could feel his bulging vein against my tongue.
When he reached the back of my mouth, I began to lightly suck as I pulled back until he was almost out. Then, I pushed forward, again, holding my tongue up against his vein. Tightening his grip on my head, he forced his cock to the back of my mouth and then pulled outward. He began to fuck my face in a slow deliberate back and forth motion. I kept up my suction as he withdrew and held my tongue tightly on his vein as he pushed back in.
After a few minutes, he began to push harder against the back of my mouth on his inward thrusts. I knew what he wanted, but I didn’t think I could take him into my throat. Still, he persisted, causing me to gag several times. This seemed to generate a coating of phlegm that was beginning to lubricate his invasive member. My hands were on his hips, sometimes pushing him away from me when he made me gag. Yet I wanted more of his beautiful cock. My arms were beginning to push and pull in sync with his hands on my head urging him to continue.
We increased our pace which made my mouth wetter. I began to be consumed with his dick in my mouth, pushing and pulling harder each stroke. In an act of desperation, I wrapped my arms around his waist and pulled tight. I could feel his cock begin to push into my throat. I moved my head around changing my angle until my throat was in an alignment that accepted his huge member. He squeezed his hands on my head as his dick was forced into my throat. He let out a moan, thrusting his pelvis forward, and raising his body by pushing up on his toes, while leaning his shoulders back. Then, he pulled out a little, followed by another almost violent thrust forward.
He grunted out, “Holy Shiiiiit!!!”
Finally, I had to push back to get some air. But I kept my arms around him to keep his cock from completely coming out of my mouth. After I was able to take a few breaths, I pulled him back into my mouth and into my throat. It seemed once he was in my throat, it became dilated, allowing me to take him in multiple times with less effort, pain, or gagging. Now he could fuck my throat and he did.
Within a few minutes he warned, “You’re going to make me cum.”
I pulled him into my throat and held him tight. He tensed up and squeezed me tight as I could feel his thick vein throbbing against my tongue as he began to pump his cum down my throat. We both held each other tight for a few seconds as he emptied his load into me. As I pushed him out of my throat to get some air, I could taste a hint of his cum in my mouth. There was a strange sensation in my throat from his warm cum. After getting some air, I put his softening cock back into my mouth, licking and sucking the few precious drops that were left in him.
He declared, “That was the best head I’ve ever had in my life.”
I helped him pull up his shorts. He said, “Let me see if the coast is clear.”
As he poked his head out and looked both ways, I asked, “Well is the coast clear?”
He laughed and replied, “No. It’s cloudy.”
He turned around and climbed down to the ground. Then, he reached up and helped me down to the ground holding the cheeks of my ass. When both of my feet were on the ground, he hugged me from behind. “That was great, will you be here tomorrow?”
I answered, “I will be now.”
We went back to our chairs where I started to secure my hook to the pole. Dan came up behind me and put his arms around me. I responded by letting my head fall back against his shoulder. He whispered in my ear, “I can’t wait until tomorrow night to see you again, but it’s getting late and I have to leave. Can I bring anything tomorrow?”
I said, “Yes, bring a condom.”
He kissed me on my cheek, “You’re the best. Good night, Baby.” Then he folded his chair and walked away. I waited a few minutes before packing up my stuff and went to the car. I reluctantly changed back into my shorts and shirt, and then drove back to the house.
When I walked in, my wife asked how the fishing was. I showed her the flounder I caught. She replied, “You must have found a good spot. It looks like we have dinner for tomorrow.”
“Yeah, I found a real good spot. I think I’ll try it, again, tomorrow night, if you don’t mind.”
“No go ahead. The girls and I are going to play cards tomorrow. I’m glad you found something good to do.”
Needless to say, the next evening I packed up my fishing gear and headed back to my new favorite spot. It was another warm night, but a little cloudy, making it darker than the night before. I changed on the side of the car, again, and walked down to the beach near the lifeguard stand so Dan could find me. I put a lead weight on my line, but no hook. Then I walked into the water and cast my line into the surf. After I walked the pole back up near the chair and put it in the sand stake, I walked back into the water until it was almost up to my bikini bottom.
The cool water felt good on my bare legs. A wave hit me wetting my bikini bottom. I’m not sure why, but I felt so sexy standing there like that. I guess I’ve had visions over the years of finding a lone woman in a sexy outfit enjoying herself. Only this time, I was the woman waiting for someone to find me. After a few minutes of frolicking in the surf, I saw a lone man walking along the beach toward me. I couldn’t tell if it was Dan. I thought to myself, I’ll stay in the water since it is dark and no one could make out my bikini anyway.
As the shadow got closer, an unfamiliar voice yelled, “How’s the fishing tonight?”
I replied, “Just getting started. You’ll have to ask me, again, in an hour or so”
“Okay, I might just do that. Good luck.”
I was getting more comfortable being out here. There was almost no fear or concern of being discovered by someone. In fact, I was excited at the prospect of meeting men on the beach. Then I heard, “Gene, is that you out there?”
“Yes, it is. How are you tonight, Dave?”
I walked up to the beach toward Dave. He held his arms out and gave me a big hug before kissing me on the lips. I have only kissed a man on his lips a few times in my life. I never really liked it before. But, tonight was different. I had a connection with Dave and I knew I would be having sex with him. He must have taken a shower before coming, he smelled clean, yet masculine. Kissing was foreplay in this case, and I wanted us both to be hot to trot. We kissed, again. This time he pushed his tongue into my mouth. I squeezed him tight with my arms before pushing his tongue back into his mouth with my tongue becoming the aggressor this time. He held my ass cheeks with his two hands. I could feel his cock against my lower abdomen. My temperature was rising and I felt like a woman beyond my wildest dreams.
When we finally finished our minute’s long kiss, Dan said, “I brought a blanket to lie on.” He took my hand and we walked to the side of my chair where he spread the blanket out. He sat on the blanket, leaning back on his arms, with his legs open. “Come sit with me,” as he pat his hands on the space between his legs.
I sat on the blanket, between his legs, with my back to him, looking out into the night surf. He wrapped his arms around me pulling me back. I leaned my head back onto his left shoulder. He began to run his hands over my chest as he nibbled on my right ear with his lips. I put my hands on the side of his thighs as I ascended into a trance. He used his fingers to strum my nipples. I could feel them harden. I was never so relaxed, yet excited at the same time. He was seducing me.
“Would you like a drink? I brought some margaritas,” he asked.
I replied, “Okay, sounds good.”
He got up and got a container and two plastic cups. He handed me a cup and then filled it. Then, he poured himself a cup. We sat there for ten minutes drinking. I was getting anxious and wanted to get back to the feelings I had before the drink intermission. I finished my drink and laid on my stomach. Dan started rubbing my back, working his way down to my ass. He pulled my shirt up over my waist.
I could feel him pulling on one of the strings that tied the top of the bikini bottom together. Then, he moved to the other side doing the same. He pulled the back down exposing my ass. His hand began to rub my bare cheeks. I began to return to that trance, again, spreading my legs apart. Dan planted several small light kisses on my cheeks. They were giving me chills. It was everything I could do to not yell out: “Fuck me you fool!”
Then, he moved over between my legs sitting up on his knees. He leaned over to his bag reaching for something. I could hear him ripping open a wrapper. The anticipation was building. He moved around a little before I could feel the tip of his cock probing the crack of my ass looking for my rear door. It found its target. He spread my cheeks with his hands as he began to push his large blunt cock into my long-neglected, yet welcoming entrance. My hands were folded under my chin and my eyes were looking out at the beach. I hadn’t even thought of the possibility of someone coming along while in this compromising position. All I could think about was Dan’s dick being inside me.
My anal ring started to yield to the large intruder. I could feel my asshole opening up as he began to enter. I could feel his helmet clearing the way for the inches of shaft behind it. There was a slight relief as my sphincter was able to contract as the larger tip passed through. I could feel the raised nubs on the condom sliding through my anal ring. My colon was being filled with his magnificent man meat. I began to appreciate his size as he packed it into me. The first penetration is always so fulfilling. My own dick was oozing pre-cum.
I could feel his balls against my cheeks as he buried his cock in my ass. I had to let out a small moan. He asked, “Does that feel good?”
I replied, “Heavenly.”
He let the weight of his body rest on top of me. Then he moved his hands under my chest, grasping my shoulders to pull himself forward along with using his knees. He started a back and forth motion messaging his cock in my ass. I pushed my ass up to give him a better angle. The coolness of the night was replaced by the heat of our passion and the friction of his cock in my tight ass. He increased his pace and we both started grunting. The grunts turned to gasps as we continued our pace for quite a while. I could detect he was struggling to keep up the pace.
I closed my legs part way forcing him to move his legs outside mine. Now he had better leverage to thrust into me. He was sitting up with his hands on my waist. As he resumed, his thrusts were more powerful in this new position. My whole body was moving up and down the blanket. My own cock was being pushed back and forth into the sand underneath the blanket. His entire weight was now concentrated on top of my ass. My colon was heating up like an oven.
I started moaning quietly, yet uncontrollably. Dan was gasping, again, as he gave all of his effort to moving his cock that was so tightly lodged deep in my ass. I started to feel a tingling inside me. Dan began to utter “Ah, ah, ah” as he was reaching a climax. I instinctively closed my legs completely. I felt like I captured a hot potato in my ass. The heat was intense. My colon began to spasm and my dick came in my bikini bottom.
Dan froze still at the top of his thrust letting out a long groan. His thighs became tense; his hands were gripping my waist tightly, as I could feel his cock pulsing inside me as he held it in me with all of his force. I was in a state of euphoria. I lay still for several minutes. Dan started to relax his body from its tensed up state. He leaned forward and kissed the back of my neck before whispering, “I’m not sure if I’ll be able to get up. You’re incredible. We would have been in trouble if someone came along.”
Another five minutes passed as we both recovered. Dan finally pulled his softened cock from my warm ass. I could feel the cool air and emptiness when he was completely out. I rolled over and sat up watching him remove the condom, placing it in a little trash bag. I waved him over to me as I sat up on my knees. I licked the cum clean from his warm cock.
When I was finished, I stood up losing my bikini bottoms from under my long shirt. I gave Dan a naughty smile saying, “Look what you did to me.” I picked up the bottoms and walked into the water. I washed the cum from my bottoms and rinsed my own dick clean of my cum, as well. Then I walked back up to the beach and asked Dan to help me put my bikini bottom back on. I held up my shirt and handed them to Dan. He looked at them for a minute trying to figure out how they worked.
Frustrated, I took them back and tied both sides before pulling them on. Then I had Dan re-tie them tighter so they wouldn’t fall down. I still felt chills when he touched me. I said, “I guess we better get going. Will I see you, again?” He said he was here for the summer, every summer. He gave me his number and told me to text him when I’m going to be here. I’m so glad I took up fishing as a hobby.
