Help keep this site alive with your VIP membership and unlock exciting site features available only to our supporting members!
VIP
$14.95
Buy Now!
MVP
$24.95
Buy Now!
Superstar
$34.95
Buy Now!
UPGRADE to get lifetime access to dig420's video section, the Meet Up! forums, AD FREE surfing and much, much more!

Crossdressers, Transvestites, and Transexuals!

  • Thread startertinylittlecd
  • Start date
  • #241
Tg 215

He raises up and moves to the head of the bed. He lowers his wet cock into my mouth and I take him deep. He moans out load and I can feel his hot cum filling my mouth, overflowing and running down my chin!
 

Attachments

  • Tran11 (152).jpg
    Tran11 (152).jpg
    36.5 KB · Views: 266
  • Tran11 (154).jpg
    Tran11 (154).jpg
    47.2 KB · Views: 247
  • Tran11 (155).jpg
    Tran11 (155).jpg
    25.8 KB · Views: 398
  • Tran11 (156).jpg
    Tran11 (156).jpg
    53.4 KB · Views: 325
  • Tran11 (158).jpg
    Tran11 (158).jpg
    31.1 KB · Views: 286
  • #242
Tg 216

When I was young my sisters used to dress me up like a girl and I was in bliss. Of course I couldn't tell anyone about it but secretly I just loved it. When mom was gone I would sneak into their room and go through their underwear drawers.
 

Attachments

  • Tran11 (161).jpg
    Tran11 (161).jpg
    29.9 KB · Views: 244
  • Tran11 (162).jpg
    Tran11 (162).jpg
    22.3 KB · Views: 182
  • Tran11 (164).jpg
    Tran11 (164).jpg
    30.4 KB · Views: 270
  • Tran11 (165).jpg
    Tran11 (165).jpg
    35.7 KB · Views: 222
  • Tran11 (167).jpg
    Tran11 (167).jpg
    23.7 KB · Views: 242
  • #243
Tg 217

One day my sister had bought some sheer white bikini panties. I was young and innocent in those days and didn't realize this meant she was starting to feel her hormones. I slipped them on and was looking in the mirror when I was startled to see our neighbor standing behind me at the bedroom door.
 

Attachments

  • Tran11 (171).jpg
    Tran11 (171).jpg
    48.8 KB · Views: 213
  • Tran11 (174).jpg
    Tran11 (174).jpg
    37.6 KB · Views: 235
  • Tran11 (175).jpg
    Tran11 (175).jpg
    65.1 KB · Views: 298
  • Tran11 (176).jpg
    Tran11 (176).jpg
    38.6 KB · Views: 219
  • Tran11 (177).jpg
    Tran11 (177).jpg
    36.8 KB · Views: 314
  • #244
Tg 218

I turned around suddenly and was surprised to see Mr. Flanagan standing there looking at me with an aroused look on his face. I could see by the bulge in his pants he was sexually turned on by what he saw. It liked being looked at and made no effort to hide my tiny hard on!
 

Attachments

  • Tran11 (179).jpg
    Tran11 (179).jpg
    29.6 KB · Views: 296
  • Tran11 (184).jpg
    Tran11 (184).jpg
    26.3 KB · Views: 186
  • Tran11 (185).jpg
    Tran11 (185).jpg
    47.4 KB · Views: 233
  • Tran11 (187).jpg
    Tran11 (187).jpg
    39.5 KB · Views: 239
  • Tran11 (191).jpg
    Tran11 (191).jpg
    24.1 KB · Views: 286
  • #245
Tg 219

It was then I knew I wanted to be a girl. I liked the feeling of power I had when I was dressed and playing my girl role. Mr Flanagan stood there for the longest time and I turned around acting like I was going to close my sisters underwear drawer. My tight little ass crack could be seen clearly through the bikini panties!
 

Attachments

  • Tran11 (194).jpg
    Tran11 (194).jpg
    40.5 KB · Views: 311
  • Tran11 (198).jpeg
    Tran11 (198).jpeg
    22.2 KB · Views: 307
  • Tran11 (199).jpg
    Tran11 (199).jpg
    22.6 KB · Views: 271
  • Tran11 (204).jpg
    Tran11 (204).jpg
    28 KB · Views: 232
  • Tran11 (205).jpg
    Tran11 (205).jpg
    51.7 KB · Views: 320
  • #246
Tg 220

"Does your sister have any other panties like those", he asked? I don't know lets look. He came over by me and we rummaged through her drawer. There was a package of thongs she had bought that were stilll packaged. I opened them and held them up. Mr Flanagan whistled and said why don't you try those on. I slid the white bikinis down and slipped into a baby blue thong that was so lacy!
 

Attachments

  • Tran11 (207).jpg
    Tran11 (207).jpg
    58.8 KB · Views: 354
  • Tran11 (209).jpg
    Tran11 (209).jpg
    24.3 KB · Views: 281
  • Tran11 (218).jpg
    Tran11 (218).jpg
    28.5 KB · Views: 245
  • Tran11 (219).jpg
    Tran11 (219).jpg
    22.1 KB · Views: 286
  • Tran11 (220).jpg
    Tran11 (220).jpg
    25.8 KB · Views: 296
  • #247
Tg 221

"What do you think", I asked our neighbor? He just whistled. "Why are you here anyway", I asked him. "Your mom called and said to check on you as she had to work late", he responded! I looked at his crotch and it was bulging out like a tent. I didn't know what that meant at that time but I think I kinda knew it was normal. I got that way when I was being dressed by my sisters!
 

Attachments

  • Tran11 (222).jpg
    Tran11 (222).jpg
    32 KB · Views: 165
  • Tran11 (223).jpg
    Tran11 (223).jpg
    36.6 KB · Views: 174
  • Tran11 (231).jpg
    Tran11 (231).jpg
    25.8 KB · Views: 169
  • Tran11 (232).jpg
    Tran11 (232).jpg
    26 KB · Views: 178
  • Tran11 (235).jpg
    Tran11 (235).jpg
    24.1 KB · Views: 226
  • #248
Tg 222

Later that week my neighbor stopped me when walking down the street and handed me a little bag. He told me not to open it until I got home in my bedroom. I hurried home and told mom I was going to take a nap before dinner. I slipped into my room and opened the bag. In it was 3 thongs, tiny and lacy! One black, one white, and one baby blue.
 

Attachments

  • Tran11 (239).jpg
    Tran11 (239).jpg
    36.6 KB · Views: 141
  • Tran11 (243).jpg
    Tran11 (243).jpg
    37 KB · Views: 211
  • Tran11 (245).jpg
    Tran11 (245).jpg
    25.2 KB · Views: 269
  • Tran11 (246).jpg
    Tran11 (246).jpg
    33 KB · Views: 157
  • Tran11 (247).jpg
    Tran11 (247).jpg
    13.7 KB · Views: 235
  • #249
Tg 223

I was so excited my hands were shaking! I hid them until later that night. I knew my neighbor was a nice man and I liked him a lot. My bedroom was in the very back of the house with a ivy arbor just outside which hid my bedroom window from anyone looking in unless they went behind the arbor. Then they were free to look in! That night I left the gate open between our yards so as not to make noise in the dark!
 

Attachments

  • Tran11 (249).jpg
    Tran11 (249).jpg
    23.2 KB · Views: 152
  • Tran11 (250).jpg
    Tran11 (250).jpg
    16.4 KB · Views: 156
  • Tran11 (251).jpg
    Tran11 (251).jpg
    46.6 KB · Views: 214
  • Tran11 (252).jpg
    Tran11 (252).jpg
    39.2 KB · Views: 172
  • Tran11 (254).jpg
    Tran11 (254).jpg
    52.7 KB · Views: 295
  • #250
Tg 224

The afternoon just drug but finally it was bed time. I showered and then slipped into the baby blue thong. From where my bed is I can look into a mirror and see my bedroom window where I had pulled the curtains open. I thought I saw a movement so I went to the window and I couldn't clearly see out but I could see a dark shape next to the arbor. I didn't let on as if I saw anything but my cock started to stir when I thought it might be my neighbor. I leaned over with my ass pointed to the window as if to pick up something and then slowly stood up. I was getting aroused and knew this was just the start!
 

Attachments

  • Tran11 (256).jpg
    Tran11 (256).jpg
    35.6 KB · Views: 295
  • Tran11 (257).jpg
    Tran11 (257).jpg
    25.9 KB · Views: 222
  • Tran11 (258).jpg
    Tran11 (258).jpg
    28.3 KB · Views: 310
  • Tran11 (260).jpg
    Tran11 (260).jpg
    40.4 KB · Views: 243
  • Tran11 (261).jpg
    Tran11 (261).jpg
    35.7 KB · Views: 247
  • #251
Tg 225

The next morning I went out and looked in the soft soil around the arbor and sure enough there were footprints. The gate was still open and I left it that way. My sisters were going away to camp for a week and I had access to all of their underwear and nighties. That night our neighbor was going to get a show!
 

Attachments

  • Tran11 (262).jpg
    Tran11 (262).jpg
    44.7 KB · Views: 237
  • Tran11 (264).jpg
    Tran11 (264).jpg
    33.3 KB · Views: 207
  • Tran11 (268).jpg
    Tran11 (268).jpg
    18.6 KB · Views: 246
  • Tran11 (275).jpg
    Tran11 (275).jpg
    37 KB · Views: 232
  • Tran11 (276).jpg
    Tran11 (276).jpg
    28.8 KB · Views: 399
  • #252
Tg 226

I was so aroused I could hardly wait for bedtime. Moms bedroom was on the second floor and in the front of the house and I was safe. She never came downstairs at night! At that age I was very effeminate looking with curly blond hair and blue eyes. My sisters said I had the most kissable looking lips. I slipped into the white thong and then put on my sisters baby doll. I walked to the window and could again see the dark shape of my neighbor.
 

Attachments

  • Tran11 (278).jpg
    Tran11 (278).jpg
    44.5 KB · Views: 223
  • Tran11 (279).jpg
    Tran11 (279).jpg
    34.4 KB · Views: 236
  • Tran11 (281).jpg
    Tran11 (281).jpg
    36.3 KB · Views: 279
  • Tran11 (286).jpg
    Tran11 (286).jpg
    41.8 KB · Views: 292
  • Tran11 (289).jpg
    Tran11 (289).jpg
    22.3 KB · Views: 309
  • #253
Tg 227

I lay down on the bed with my ass facing the window. It was not more than two feet from the window. My cock was hard as a rock and I rolled over on my back pretending to read a book. I could glance under the bottom of the book and see the window. He had slipped closer and I could see his face clearly now. I reached down and put my hand inside the thong rubbing my cock.
 

Attachments

  • Tran11 (294).jpg
    Tran11 (294).jpg
    21.3 KB · Views: 166
  • Tran11 (295).jpg
    Tran11 (295).jpg
    47.4 KB · Views: 305
  • Tran11 (300).jpg
    Tran11 (300).jpg
    16.1 KB · Views: 230
  • Tran11 (306).jpg
    Tran11 (306).jpg
    14.4 KB · Views: 234
  • Tran11 (307).jpg
    Tran11 (307).jpg
    31.4 KB · Views: 197
  • #254
Tg 228

I was so enjoying laying there in his view. I loved the feeling that was going through my body. I spread my legs and pulled my cock out over the top of the thong! I was so hard and sensitive! I laid the book down and looked right at him. I stroked my cock making no more pretense not seeing him.
 

Attachments

  • Tran11 (304).jpg
    Tran11 (304).jpg
    30.7 KB · Views: 206
  • Tran11 (308).jpg
    Tran11 (308).jpg
    26.2 KB · Views: 281
  • Tran11 (310).jpg
    Tran11 (310).jpg
    24.8 KB · Views: 259
  • Tran11 (311).jpg
    Tran11 (311).jpg
    50 KB · Views: 259
  • Tran11 (312).jpg
    Tran11 (312).jpg
    42.3 KB · Views: 225
  • #255
Tg 229

He was watching me intently as I stroked my cock. He rose and unzipped his pants. I could see he was aroused and when his cock came into view I saw how tiny I was compared to him!
 

Attachments

  • Tran11 (315).jpg
    Tran11 (315).jpg
    35.3 KB · Views: 194
  • Tran11 (317).jpg
    Tran11 (317).jpg
    52.1 KB · Views: 214
  • Tran11 (319).jpg
    Tran11 (319).jpg
    41.7 KB · Views: 182
  • Tran11 (320).jpg
    Tran11 (320).jpg
    31.6 KB · Views: 208
  • Tran11 (321).jpg
    Tran11 (321).jpg
    46.1 KB · Views: 240
  • #256
Tg 230

I so wanted to feel that rod but I knew I couldn't. I rolled over on my tummy and slid the thong down showing him my cute little butt hole all hairless and tight!
 

Attachments

  • Tran11 (322).jpg
    Tran11 (322).jpg
    36 KB · Views: 213
  • Tran11 (323).jpg
    Tran11 (323).jpg
    44.1 KB · Views: 231
  • Tran11 (326).jpg
    Tran11 (326).jpg
    29.3 KB · Views: 371
  • Tran11 (327).jpg
    Tran11 (327).jpg
    34.2 KB · Views: 225
  • Tran11 (330).jpg
    Tran11 (330).jpg
    38.7 KB · Views: 213
  • #257
Tg 231

I tried to slide a finger inside me but I was to tight! I knew this wasn't going to stop here but I was frightened of anyone finding out about what I really wanted!
 

Attachments

  • Tran11 (331).jpg
    Tran11 (331).jpg
    37.6 KB · Views: 257
  • Tran11 (332).jpg
    Tran11 (332).jpg
    22.3 KB · Views: 236
  • Tran11 (333).jpg
    Tran11 (333).jpg
    54.6 KB · Views: 242
  • Tran11 (334).jpg
    Tran11 (334).jpg
    26.1 KB · Views: 222
  • Tran11 (335).jpg
    Tran11 (335).jpg
    10.9 KB · Views: 282
  • #258
Tg 232

When I turned over he was gone. I was hurt that he didn't stay longer but this was to become a regular ritual for us! My erotic life was just beginning and I was to become the hottest tranny in our town!
 

Attachments

  • Tran11 (338).jpg
    Tran11 (338).jpg
    27.6 KB · Views: 225
  • Tran11 (339).jpg
    Tran11 (339).jpg
    33 KB · Views: 302
  • Tran11 (341).jpg
    Tran11 (341).jpg
    55.4 KB · Views: 228
  • Tran11 (342).jpg
    Tran11 (342).jpg
    22.3 KB · Views: 255
  • Tran11 (343).jpg
    Tran11 (343).jpg
    32.7 KB · Views: 229
  • #260
Tg 233

After that night I would tease my neighbor any way I could think of. I would lay in the back yard sunbathing when the family was out of he house. The tiny thongs would barely cover my cock and balls. He would watch from his upstairs bedroom window.
 

Attachments

  • Tran11 (344).jpg
    Tran11 (344).jpg
    38 KB · Views: 161
  • Tran11 (345).jpg
    Tran11 (345).jpg
    39.8 KB · Views: 176
  • Tran11 (361).jpg
    Tran11 (361).jpg
    34.3 KB · Views: 242
  • Tran12 (1).jpg
    Tran12 (1).jpg
    30 KB · Views: 396
  • Tran12 (2).jpg
    Tran12 (2).jpg
    49.8 KB · Views: 202

Users who are viewing this thread