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An eight part story about cross dressing, sex and friendship.
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Da_Vida
Da_Vida
172 Followers

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Part 1

My name is Nelson and this is about my college experience, which came a bit later for me than for most. After high school, where I had mostly concentrated on football, girls, friends and classes in that order, I joined the army. I spent six years in the U.S. Army Rangers and served tours in Iraq and Afghanistan. At the end of my enlistment, I'd had seen enough fighting, dying and macho bullshit to last me the rest of my life. I decided it was time to take my leave of the military and use some of the benefits that I had earned. After discharge, I hung around my home town for a few months getting acclimated to being a civilian again and investigating colleges. I narrowed down my choices to three respected state supported schools and put in my applications.

I arrived on campus in the fall along with all of the other freshmen and was given a dorm assignment. I headed over to the dormitory and located my room. Upon entering the room I was struck with how similar it looked to on-base living accommodations for junior officers, which mind you was a considerable step-up from what I had been accustomed to. After first taking in the physical space, I noticed that there was someone lying on one of the beds. The young man had been reading but had put the book down on his stomach and was looking in my direction. I say young man but I was really thinking, "damn I'm rooming with a kid." I grinned and said, "Hello, my name is Nelson." as I dropped my gear in the doorway and advanced toward the bed with outstretched hand.

The kid's name was Terry and he looked to me to be about fifteen years old. He had an innocent looking face, which by the way had probably never seen a razor, longish hair and a slim soft body on a small frame. If I didn't know better I'd thought I was approaching a teenage girl whose breasts hadn't developed. I sized him up to be about five and half feet in shoes and weighing in at maybe 120 pounds, which was something of a contrast to my six feet and 180 pound hard body.

Terry seemed like a sweet kid but was a little on the shy side. However, I'm pretty outgoing and so we kind of balanced out. This was Terry's first experience away from home. He was apparently bright because he had a full academic scholarship. As classes got underway, we spent a good deal of time studying. Usually, we'd end up at the end of an evening with some downtime and would talk. He was quite interested in hearing about some of my combat experiences and I think took me for his idea of a masculine man. I suspected the kid was idolizing me as if I was some kind of rock star or something. He looked at me in the same sort of way that some of the girls in high school looked at me after I became something of a star player on the football team.

During the fall semester break most of the dorm had emptied out. Terry wasn't interested in going home nor was I and neither of us had anywhere else we especially wanted to go so we were just hanging out. The first Saturday evening I decided to dig out a little weed that I had hidden in one of my bags. I was ready to get mellowed out a bit and I thought I'd introduce Terry to getting high.

Terry was a little reluctant at first but he didn't take much persuading. We soon had a pretty good high on and began listening to some of my music and talking. Terry had gotten quiet and seemed to be enjoying just sitting there listening to the music. I decided that what I wanted to do was go take a nice hot shower. I became very partial to hot showers after spending a lot of time in the field for extended periods. I found that they were especially refreshing when one was stoned. I said I'd be back in a few and left to take a shower. I was gone about thirty minutes and came back into the room dried down and with a towel wrapped around my waist. I must admit that while I was in the shower I passed the time with some erotic fantasy and the towel was a bit distended by my erect member. I stretched to flex my heat softened muscles and the towel popped loose where it was tucked into my waist and dropped to the floor.

Right away I noticed that Terry's eyes were riveted on my hard cock. I don't know why but after a few moments passed and he had not looked away I suddenly felt compelled to say to him, "You can touch it if you like."

Terry's hand began to rise and hesitantly move toward my rigid pole as if drawn by a magnet. As his hand reached for me he looked up at my face as though to judge my reaction. I smiled slightly and continued to look into his eyes. When his fingers made contact with my firm, hot flesh, it was like a jolt to both of us. I shuddered slightly and his eyes widened a bit and a smile came to his lips. He let his finger tips slowly and lightly move along the shaft of my ample cock while gazing into my eyes. He looked like he wanted to say something but couldn't quite get it out. I became very aroused by his touch and began to breath more heavily. Terry wrapped his hand around the shaft and held my cock as if he were going to jack me off and squeezed the shaft tightly several times, as if testing it's firmness. By this time I was so excited that I badly needed some relieve and while still gazing into Terry's eyes whispered, "Kiss it."

Terry leaned forward and experimentally kissed the engorged head of my rigid cock. Then his tongue came out and licked off a bit of lube oozing from the tip. His tongue took the small treasure back into his mouth where he examined the taste. Apparently, I passed the taste test because in a moment he came back and squeezed a larger globule of the slick, thick, clear liquid out of the shaft and onto his extended tongue. I was now too excited to remain on my feet and moved to sit down on the couch beside Terry. Once sitting I swung one leg over and behind him so that he was sitting between my legs. I then leaned back and rested my head on the pillow against the arm rest at the end of the couch.

Terry leaned over and down to get his mouth back into proximity with my dick and took the head into his mouth. He licked and sucked on the head while grasping the shaft in one hand so that he could keep my member in position. He slowly moved the head in and out of his mouth letting the fluid coming out of the tip lube his lips so that the head slid easily between his lips. While he moved up and down on the head his tongue was busy stroking the underside of the head and shaft. It didn't take long until I knew I was going to ejaculate. Just as he slid the head well into his mouth I groaned and the dam erupted. I nearly passed out as I felt convulsions sweep over my body thrusting one glob of semen after another out of my balls, through my shaft, out the tip and into Terry's eager mouth. I could feel the mouth around the head of my cock holding on tightly and capturing every drop that erupted into it. After I exhausted my supply of cum and the convulsions stopped, I felt my cock slip from Terry's mouth and heard him swallow several times clearing my cum from his mouth and taking it deeper into his body. In a moment he was back licking up every trace of cum from my cock.

I opened my eyes and looked down to where Terry sat between my legs. When I made eye contact with him he looked away and appeared embarrassed or ashamed. I felt great and I did not want him to feel badly about giving me so much pleasure. I swung my leg over his head, sat up and turned toward him. I reached over with my hand and turned his face toward me and quietly said "thank you," while looking into his eyes. I then cupped his face in my hands and pulled him closer and gave him a lingering kiss on his lips. When I pulled back he gave me a faint smile and seemed a bit reassured. I said, "Go and get cleaned up and let's go out and have a great dinner."

Later after we returned to the room we had a few more tokes on a joint. Terry confessed to me that he had never sucked a cock before but had imagined what it would be like to be a hot girl and to go down on a guy. He told me that he had a small collection of lingerie that he had been accumulating since puberty and that he often put it on and masturbated while imagining having sex with a man. I told him that I didn't mind if he wore panties of anything else feminine and that as long as I was around he didn't need to imagine having sex with a guy. Terry told me that sucking my cock while wearing panties was his fantasy come true. Apparently, we were a great match because I love blow jobs and he loved giving them.

We were both sleepy from the grass and I suggested that we lie on one of the beds, which were for a single occupant but Terry was fairly small. I stripped down to my shorts and when Terry dropped his pants I was not surprised to see that he was wearing flesh colored panties with little lace insets on either side. We lay in bed spoon fashion and I enclosed Terry's upper body in my arms. I began to caress his naked skin which from the soft cooing sounds he was making I gathered he found stimulating. After the great blow job he had given me I was happy to reciprocate in some small way. I soon found that brushing my finger tips over his little nipples made them hard and erect. I cupped what little breast flesh the nipple inhabited and began to gently massage the flesh in my hand. I ran my hand down his body and over his nylon clad buttocks. As I did this, I confessed to him how erotic I found caressing buttocks covered by nylon panties.

About a week later I came in one evening after having spent some time in the library doing research and found Terry strutting around the dorm room in a pair of high heels, which he confessed he had been secretly practicing walking in for a couple of days. I noticed that he was also wearing nylon stockings with the shoes. I was curious to see what he was wearing under his jeans. I pulled Terry to me and gave him a hug while gripping his ass in my hands and felt the unmistakable feel of fabric slipping across nylon. I took hold of his t-shirt and pulled it over his head and then unfastened his jeans. I pushed the jeans down and found that he was wearing hot pink, nylon hip huggers along with a black garter belt, which was holding up his nylons. I sat him down and took his high heels off, pulled his jeans off and then replaced the shoes. I stood up and said, "Now, let's see how you look."

It appeared that Terry had removed all of what little body hair he had because his skin was completely bare. He walked around a bit in the somewhat confined space but he carried himself well and looked great. His practice walking in high heels had been successful as he pulled it off smoothly and with grace. He walked over to me and looked up into my face and asked, "Do you like?"

I looked back down into his eyes and replied, "I love what I see." I enfolded him into my arms hugging his face into my chest and reached down and cupped his panty clad buttocks in my hands. I began to caress his butt through the panties, which was a very erotic feeling. I soon noticed my cock straining against its restraints. Terry must have felt it also because he began unfastening my pants and pushing them down to let my erect member stand at attention. He took it in his hand and gazed up at me with a questioning look on his face to which I merely nodded in the affirmative. In a moment, Terry had dropped to the floor on his nylon clad knees and began ministering to my needy cock. I was really turned on by watching this sweet boy wearing pink panties, stockings and high heels down on his knees sucking my dick for all he was worth. I took hold of his head in my hands and stroked the back of it with my fingers as he lovingly sucked on my cock. Shortly, I pumped his mouth full of my love juice and collapsed back against the wall. When I opened my eyes, Terry was looking at me with a self-satisfied grin on his face.

We were soon ready for bed and to my surprise Terry brought out some sexy satin pajamas that he put on after taking off the high heels and hose. I asked him to lie on the bed with me for a few minutes. Once again we got into the spoon position and I enfolded him in my arms. This time, however, I wanted to give him something in return. I caressed his satin clad body and eventually found his crotch. There I found his modest member aroused and pressing against his panties. I maneuvered his prick so that it was lying parallel to his body, against his abdomen and with the underside of the shaft facing upward. I began sliding my open hand gently up and down the length of the shaft and down on to his balls feeling the satin pajamas easily sliding across the nylon panties. Terry was soon moaning and pushing against my hand to increase the friction. Before long I felt him begin to convulse as he shot his load into his panties and over his abdomen. I gave him a big hug and held him for a few minutes and then told him he should go clean himself up. Before he returned I fell asleep. The next morning I found him sleeping contentedly in his bed still wearing the satin pajamas.

During the balance of the school year Terry became the ideal roommate. He kept our room clean, did the laundry and generally took care of all the domestic duties. When we were alone in the room, he always wore something sexy under his male clothing and loved to wear high heels and stockings. I loved the way the high heels caused him to move and make his tight little butt stick out in a manner that invited me to grab it from time to time. Several times a week, Terry gave me great head, which could only have been done so well by someone who loved to suck cock. I could tell he got a thrill from making my cock erupt cum and he seemed to savor the taste and smell of my copious semen. I continued to occasionally masturbate him by friction between my open hand and his sexy attire.

I regretted the end of the spring term because I knew that our cozy little sex affair would have to come to an end at least temporarily. We rented a storage locker where he could leave much of his growing collection of girl clothes. After storing some of his things, I took him to the bus station and saw him off for home. I had picked up a full time job for the summer and was staying. Not being a student during the summer, I had to leave the dorm and found an apartment nearby.

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Part II

I missed having Terry around but was pretty absorbed in my summer job. One evening after work, I felt like a little social life and went to a nearby bar for a couple of drinks. After sitting down at the bar and ordering a drink, I began checking out the establishment and its patrons. Right away I noticed a very good looking, dark complexioned, lady with long black hair sitting at a table. She was surrounded by a cadre comprised of most of the unattached guys in the bar. She didn't seem to mind the attention and free drinks but didn't appear to be taking any of her would be companions seriously. I caught her eye a few times and smiled but didn't make any effort to join the fray. After a couple of hours or so and a few drinks, it appeared to me that the young lady was getting bored with the attention and I decided to test my hypothesis. I rose from my bar stool and walked over to the table where she sat along with several of her admirers. As I approached I was encouraged when she looked up at me and smiled. When I got to the table, I said, "Hi, it appears to be a lovely evening out tonight and I was wondering if you'd be interested in joining me for a walk on campus?"

She looked up at me and with another smile and twinkle in her eyes said, "Yes, that would be nice." She rose from her chair and told her admirers that she had to leave now and thanked them for the drinks and company. We then made our way across the room and out of the bar. As we were leaving I glanced back at the table we had just left and three guys were just sitting there watching our exit with dumbfounded looks on their faces.

This beautiful lady's name was Arlene and she was also a student at the university. While we were close in age she was an advanced graduate student who was studying to be a counselor. We went out several times for dinner and took in some movies. One weekend after we had become comfortable with one another, I suggested that we go to a nearby lake for a camping trip. Arlene readily agreed and so early on a Saturday morning I swung by the house she was renting to pick her up. She came to the door and looked stunning. She had her long black hair pulled back in a pony tail. She wore no make-up but her Mediterranean coloring, flawless skin and sparkling eyes turned her well proportioned face into an image of natural beauty. She wore tight denim short-shorts and a sleeveless blouse that tied up under her modest but pert breasts leaving exposed an expanse of beautiful skin. Her long shapely legs ended in feet with bright red toe nails and clad in leather sandals.

I had gone to the local Wal-Mart the evening before and picked up a tent and other camping gear. I had the gear stored in the trunk of the used car that I had bought to get back and forth to work. I helped Arlene get a few things that she was taking out to the car and stored them in the back seat. I told her that we still needed to stop by a grocery and pick up some food and beverages. As we drove out of town toward the lake, I spotted a suburban grocery store in a shopping center and pulled in. We headed into the store and began locating items for our shopping cart. As we walked up and down the aisles, I noticed that most of the male employees and customers had to take a second look as they went past us. Arlene seemed oblivious to their interests but I fully understood it because I had could hardly keep my own eyes off of this lovely example of feminine beauty.

After arriving at the camp ground and locating a suitable place to pitch camp that wasn't too close to any other campers we went about setting up camp. By the time we finished we were both hot and sweaty and decided to take a swim in the lake to cool off. Arlene went into the tent and changed into her swim suit, which was dusty colored two-piece suit that at first glance almost made you think she was nude. I went in the tent and changed into my swim trunks and we went down to the lake. We were camped on a little finger jutting out into the lake that formed one side of a small inlet. We found a good place along the shore of the inlet to enter the water and were soon enjoying a nice refreshing swim. Arlene was a good swimmer and was playful in the water. Once she went under and I lost track of her until she popped up right in my face laughing at my surprised look. She put her arms around my neck and held herself close to me. I leaned my head a bit toward her and she moved her head toward mine and soon found myself engaged in a deep passionate kiss. We were not too far out and I was tall enough to stand on the bottom and keep my head out of the water. Arlene kept her own head above water by clinging to me. Between our kissing and the feel of her tight, shapely body pressed against mine, I was soon very aroused, which I knew she could not fail to feel. I was hoping that she would not take offense when she whispered in my ear that she thought we should return to the tent and "rest" for a bit. I could tell by the sultry way she spoke that rest wasn't exactly what she had in mind. I readily agreed and we started for the shore.

Once we were in the tent we quickly stripped off our swim suits and were soon tightly embraced in one another's arms. I could feel her firm breasts spreading out against my torso from the pressure of our embrace. We completed several long, slow kisses and then gazed into each other's eyes as our bodies separated a bit. My rigid cock was pressing into Arlene's abdomen. She reached down and took it in her hand as she raised up on her toes and slid it between her legs. She sat astride my member squeezing it between her legs. I knew that it was a strain on her to stay elevated enough to hold this position so I put my hands under her arms and lifted her up. She wrapped her legs around my waist leaving my erect member protruding under her buttocks. I squatted and lowered us down and then over onto a sleeping bag.

Da_Vida
Da_Vida
172 Followers