Gogol's Adult Life
Some of Gogol's longest lasting friendships were formed while he attended a private boarding school at Nezhin. He attended this school from age 12, shortly after his younger brother's death, until age 19. It was an all-male school, and Gogol participated in both literature and drama, often playing the female roles in dramatic productions (Karlinsky, 13). This aspect of his adolescent life may have no connection with his later transvestism, since cross-dressing by male actors had been widely accepted in drama for centuries for the purpose of playing female roles. However, Gogol's homosexual interests were already strongly established by this time, as can be seen in one of the letters he wrote to an older student who had just left the school.
After Gerasim Vysotsky left Nezhin for St. Petersburg, Gogol planned to join him and sent him many affectionate letters. One letter dated March 19, 1827 begins: "So you do love me after all, my kind, precious friend. You sacrificed a portion of your valuable time in order to give joy to someone who burns for you with an unfathomable, ardent attachment". He goes on to finish "Yours till the grave, unchanging, faithful, eternally loving you, Nikolai Gogol" (Karlinsky, 15). Unfortunately for Gogol, Vysotsky did not return his amorous feelings, and after leaving Nezhin, Gogol was apparently rebuffed by Vysotsky.
In conflict with his (homosexual) attraction to men, Gogol seems to have been attracted specifically to heterosexual men in almost every instance. This was the case with Gerasim Vysotsky at the beginning of his life, as it was with Nikolai Yazykov in later years. This attraction to heterosexual men has been described as a way for a homosexual man to deny his own homosexuality (Karlinsky, 308). The rationale seems to be that if a man is attracted to a heterosexual man, then he is obviously not homosexual, but simply attracted to an individual who inconveniently happens to be another man. Kiell, however, describes this attraction to heterosexual men as a normal consequence of the transsexual's belief that he is truly a woman.

He prefers normal, heterosexual men as sexual partners, and rejects homosexual men or the idea that his sexual activity is homosexual. Feeling he belongs to the female gender, he considers it appropriate to have a love relationship with a man, and feels 'unnatural' in a relationship with a woman, considering this 'homosexual'. (332)

He is constantly being cheated and swindled and fleeced by the Italians, whom he trusts as if they were honest and whom he respects exceedingly. He spends money as if it were dirt and fusses and bustles, being quite sure that he outsmarts everyone and buys everything cheaper than the others, and takes pathological offense if he is contradicted in anything. (Karlinsky, 224)

Cross-dressing Activities
Throughout his adult life, Gogol was fascinated with such things as clothes and fabrics, and "[h]e particularly liked brocaded and embroidered vests (the art of embroidery had interested him since his early youth, and a considerable portion of his correspondence with his mother during his stay in St. Petersburg is devoted to embroidery patterns and designs)" (Karlinsky, 205).
This phenomenon has a correlation in the case studies of transsexual boys, gathered by Stoller (1968, 336-344). In one particular case, involving a four-and-a-half year old boy who was diagnosed as transsexual at a very early age, the boy not only enjoyed feeling and wearing feminine clothes and fabrics, but in his behavior he somehow linked the wearing of feminine clothes to creative expression. In opposition to the definition of cross-dressing by transvestites above, this boy did not wear women's clothes for reasons of sexual arousal. Instead, he usually wore women's clothes while engaged in drawing. In the classroom, the boy would go to the dress-up box and pick out a skirt, bolero jacket and high heels. Once he had this outfit on, he would begin drawing. His drawings were described as very advanced and detailed for a child his age. At one point, however, the child was transferred to a different classroom where he was not permitted to dress up except during playtime; the boy then stopped drawing (Stoller 1968, 339). In this example we can infer that creative expression was somehow linked to the new identity assumed by the boy when he was allowed to 'become' a woman.
This connection of cross-dressing with creativity, rather than sexual arousal, may be seen in the single documented instance of transvestism by Nikolai Gogol. On this occasion, Gogol was surprised in his room by two friends, Vasily Zhukovsky and Sergei Aksakov, in an episode described by Aksakov in his memoirs.

"There was Gogol in front of me, wearing the following fantastical costume...Instead of boots, he wore long woolen Russian stockings, reaching higher than the knee; instead of a jacket, a velvet spencer worn over a flannel camisole; around his neck was a large multicolored scarf and on his head was a crimson velvet woman's headdress (kokoshnik), embroidered in gold and very similar to the headdresses of Finnish tribeswomen." Gogol did not seem to be particularly embarrassed at being caught in this outfit. He simply asked Aksakov what his business was and then dismissed him by pleading the need to go on writing. (Karlinsky, 205-206) [see Appendix]