The use of --with-curses-dir=/usr in CONFIGURE_ARGS causes the makefile to prepend a  -L/usr preceding the -L/usr/local when linking with ssl, causing the port to always use the base ssl library rather than that of security/openssl, even when WITH_OPENSSL_PORT is set.  Here's one way to fix it (of course, in the future, if security/gnutls or devel/ncurses or devel/libslang2 support is enabled, a better fix will be required):

diff -ruN lynx.orig/Makefile lynx/Makefile
--- lynx.orig/Makefile	Fri Nov 16 03:23:23 2007
+++ lynx/Makefile	Fri Nov 16 03:19:27 2007
@@ -24,8 +24,8 @@
 WRKSRC=		${WRKDIR}/${PORTNAME}2-8-6
 GNU_CONFIGURE=	yes
 CONFIGURE_ARGS+=--with-screen=ncurses --with-zlib --libdir="${L_LIB}" \
-		--enable-nsl-fork --enable-persistent-cookies --with-ssl \
-		--with-curses-dir=/usr
+		--enable-nsl-fork --enable-persistent-cookies --with-ssl="${OPENSSLBASE}"
+SUB_FILES=	pkg-message
 
 .if defined(WITHOUT_NLS)
 CONFIGURE_ARGS+=--disable-nls
@@ -57,8 +57,6 @@
 
 post-patch:
 	@${RM} -f ${WRKSRC}/CHANGES.orig
-	@${REINPLACE_CMD} -e 's|-lssl -lcrypto|-L${OPENSSLLIB} &|g' \
-		${WRKSRC}/configure
 
 post-install:
 	${CHOWN} -R ${SHAREOWN}:${SHAREGRP} ${DOCSDIR}
diff -ruN lynx.orig/files/pkg-message.in lynx/files/pkg-message.in
--- lynx.orig/files/pkg-message.in	Wed Dec 31 19:00:00 1969
+++ lynx/files/pkg-message.in	Fri Nov 16 03:40:04 2007
@@ -0,0 +1,13 @@
+To enable certificate handling for SSL connnections, set
+SSL_CERT_DIR and SSL_CERT_FILE in your environment to the
+proper values (depending upon which SSL library
+%%PREFIX%%/bin/lynx uses), as described in:
+ 
+%%DOCSDIR%%/docs/README.sslcerts 
+
+and:
+
+%%DOCSDIR%%/docs/README.rootcerts.
+
+You may also need to generate keys and certificates as
+described in the latter document and your SSL documentation.